Cruisers often bypass the small and lesser-­known southeastern Bahamian islands on their windward passage through the Exumas on their way south to the Caribbean. But they shouldn’t. Take the advice of Bruce Van Sant, legendary sailor and author of The Gentleman’s Guide to Passages South: “Don’t rush through the islands; they are too perfect.” So, Google up a map, friends, and follow along. 

Because the Bahamas are shallow, the water they occupy in the North Atlantic Ocean is that much lighter, and, frankly, more beautiful than the Caribbean Sea. You can sail for miles in 10 to 15 feet of the lightest hues of blues and turquoise, suddenly plunge into thousands of feet of dark blue ocean, and return to shallow turquoise toward the edge of the next island. The shelf acts and feels like a large V.

Conception Island is possibly the most beautiful of all the Bahamian islands and is only 45 nautical miles northeast of popular George Town on Great Exuma Island. As Van Sant suggests, to reach Conception Island, anchor the night before just south of George Town at Fowl Cay, an uninhabited island with a small swimming beach. This will save you 4 miles of motoring to exit Great Exuma. Raise your mainsail at first light, and a southwestern wind will give you one long, straight starboard tack to Conception Island. Uninhabited and pristine, the beach has water so clear, you’ll swear you can drink it. The whole island is less than 3 miles at its widest, and it’s low-lying like all the small Bahamian islands, making it almost unnoticeable on electronic or paper charts.

The Bahamas National Trust has designated Conception Island a national park, which protects conch, fish and lobsters. The coral heads and reefs that surround the island make for great snorkeling and diving. At high tide, an entrance to a creek two-thirds of the way down the western side allows you to dinghy into mangrove flats to see turtles, sharks, conch and other marine life.  

To relax, simply walk the deserted white sandy beach and let your mind wander in your escape to this stunningly beautiful anchorage. Or, from the deck of your boat, simply stare at the magnificent crescent-shaped beach, and imagine why no more than five sailboats and catamarans are anchored outside the island on any given day.  

Like this solo sailor, you might chance upon the only other sailors on the beach who happen to know the Bahamas like the backs of their hands. If you are fortunate, like me, they will buddy-sail with you 35 nautical miles northeast to San Salvador. There, anchor in deep white sand just east of the only town on the island, and your new friends will take you to their favorite coral head, where they will spear two huge spiny lobsters and share their spoils in a tasty dinner on their catamaran. For thanks, buy them cocktails the next day at one of the only open bars ­overlooking the beach.

Sparsely populated and somewhat larger than Conception, San Salvador Island hosts a handful of small resorts and, surprisingly, an airport that brings in daily flights from Florida. Still, it maintains the feel of a quiet and secluded Caribbean island. You can walk the traffic-free main road, and a friendly local might drive you to one of the two small grocery stores on the island. Much controversy surrounds the claim that Columbus made his first landfall in the New World at San Salvador Island, though a plaque on a building in the middle of town states that he landed there October 12, 1492.

From San Salvador Island, you can sail 30 miles southwest to Rum Cay in prevailing east winds. (An island with the word rum in it must be good.) Find yourself wind-protected on the absurdly beautiful, quiet and pristine Flamingo Bay on the western edge of the island. Your charts will show a submerged wreck, giving you fair warning to watch the depth and weave the coral heads using eyeball navigation. You can sleep soundly under a clear sky and shining stars in tranquil water. Among life’s finer experiences, one should enjoy a morning cup of coffee on the bow of a gently swaying sailboat in a warm, clear bay that is yours and yours alone. Dinghy to the deserted shore to create the only tracks on the white-powder beach.

On a rising sun, sail out of Flamingo Bay against an east wind to seek civilization around the corner to Port Nelson, the only inhabited town on the island, with reportedly fewer than 100 residents. With a handful of tacks, you will turn a 6-mile sail into 15 glorious sailing miles where you will see small flying fish burst out of the water to escape predators. At 30 miles in total area but still tiny in size, Rum Cay dwarfs Conception Island.

Port Nelson consists of a welcome sign and a government dock that accepts a mail boat three times a month. Near the dock, you might find yourself at The Last Chance, a ramshackle bar with sand floors, a pool table and a book rack. Kaye Wilson, the proprietor, will sell you a Bahamian beer for $3, a dozen eggs for $8 or a bag of frozen green beans for $6. She also will make you the tastiest burger for $12 and serve it in a foil wrap rather than on a plate. 

You might chat up the only other patrons, two Bahamian police officers also enjoying a lunchtime burger. Even though the island is crime-free and all residents know one another, the officers are on daily foot patrol. One might be wearing a polo shirt, while the uniform of the other is a ball cap and T-shirt that say “police.”

Don’t shy away from requesting a police escort to the only other open eatery, the Ocean View Restaurant, an establishment with wood floors that’s been proudly owned for 45 years by Ruby Bain. Her son will serve you a Guinness in a bottle delivered to the island on a mailboat. I watched in awe as she affectionately taught one of the officers a local song. After you share a beverage with the police and they insist that you stay on the otherwise sleepy Rum Cay for a weekend festival, you know that you have met some of the friendliest people on Earth.

To seek protection from an oncoming stiff and persistent eastern blow, depart Rum Cay at 4 a.m. and motorsail 30 degrees off an east wind to reach the western side of Crooked Island in daylight, some 60 miles southeast. You might find several sailboats and catamarans already there seeking shelter. 

At Crooked Island, it is impossible not to make new sailing friends, either on the beach or at Gibson’s Restaurant, where they seat customers, mostly sailors, cafeteria-style on a long table. They serve everyone the same delicious fare of locally caught fish, meat and vegetables.

Take the advice of legendary sailor and author Bruce Van Sant: “Don’t rush through the islands; they are too perfect.” 

At Crooked Island, you also might be lucky, like me, to find a stainless-steel spear pole washed up on the beach that you can use to spear your own lobsters. If you need diesel and water, motor a few miles to the Crooked Island Lodge and Marina, the only marina on the island. You might as well spend one night there instead of rolling on anchor in the big blow. The ­marina’s knowledgeable ­general manager will show you the nearby coral heads to hunt lobsters. (Using the ­newfound pole spear, this ­novice ­fisherman came up empty-handed, but the ­marina’s chef prepared a lobster dinner for me, the restaurant’s only customer for the night.)  

Sailors can do major provisioning at the marina for Bahamian beer, wine, local fish, vegetables, frozen hamburgers and delicious rolls. And what the marina does not have, the general manager will drive you 4 miles to find at the small grocery store. The marina is undergoing big renovations, including new hotel rooms, small cabana-like lodges, a new restaurant and a pool. It is also enlarging its jetty, so boats will enjoy a swell-free dock experience.

So far, you will have had days of pain-free windward sailing. That might end as you sail east toward the lightly populated Mayaguana Island, a staging ground for a ­southeast run to Turks and Caicos. If you have no time to wait for a favorable wind north of east, you might ­experience moderate bow-bashing and ­wave-crashing sailing to the small and uninhabited West Plana Cay, a good stop-off 43 miles toward Mayaguana. After you pass Acklins Island off your starboard and you steer 30 or so degrees south, the waves begin to behave, and you will reach West Plana Cay in calm conditions.  

Again, you will have all to yourself another beautiful ­turquoise-blue bay protected by an east wind, and you will ask why you are not ­spending long days there reading, beachcombing, fishing, ­sleeping, and just enjoying your escape from civilization. 

Last, the 37-mile east sail from West Plana Cay to Abraham’s Bay on Mayaguana will likely be similarly uncomfortable. Protected by a barely visible long stretch of coral reef, Abraham’s Bay will feel like you are ­anchoring in 15 feet of open ocean, but the overnight roll will be ­moderate and easy to handle. 

The next day, sail east in 14 miles of pain-free ­tacking across a small bay to Southeastern Point, where Van Sant suggests that you stage your departure to Turks and Caicos. From this point, you will have a better ­southward angle to sail a reach to Sapodilla Bay on the Caicos banks.

Damian LaPlaca is currently in Puerto Rico aboard his Jeanneau Sun Odyssey 39i Performance, Beckon.

The post Cruising the Southeastern Bahamian Islands appeared first on Cruising World.

I’m no Ernest Shackleton. I live in Hawaii, and I love the warm weather and clear blue waters of the tropics. Having done a little high-latitude sailing, I have to admit that freezing weather is not my favorite. My boat doesn’t even have a heater.

Yet here I was with Tracy, a surfing friend from Hawaii, ripping down Puget Sound at 12 knots under spinnaker, in the dead of winter. I had on about 10 layers, two puffy jackets, gloves, boots and a hat. I also had a huge smile on my face.

This was shaping up to be an ideal adventure, filled with solitude and unexpected experiences. It was also some of the best sailing I’d done on my Jeanneau 509, Kāholo. And it had all started with simple necessity: I had to move the boat to get new canvas.

In 2021, I had sailed ­new-to-me Kāholo 5,000 miles, across the Atlantic and the length of the Caribbean, from Portugal to Panama. While soaking under the torrential rains of Panama, I realized I definitely needed new canvas. Once we got to the Pacific Northwest, I learned that Iverson’s Canvas in Olympia, Washington, had a yearslong waiting list. And its team would not travel to your boat. Like the Soup Nazi in Seinfeld said, “No soup for you!” Unless you were ­prepared to travel.

Olympia is on the South Sound near Tacoma, 80 miles south of my winter berth in La Conner, near the San Juan Islands. Although I managed to secure a spot on Iverson’s busy schedule, the only date its team could do the work was in mid-February, the coldest month of the year.

Well aware of the shifting weather systems in Puget Sound, I stacked things in my favor by leaving plenty of time to choose a weather window. As luck would have it, a high-­pressure system was set to fill in, bringing a favorable, but very cold, northerly wind. To get ready for the next day’s northerlies, Tracy and I made a short sail out to the historic town of Coupeville on Whidbey Island, where we spent time in a warm pub with the colorful local crowd that had replaced the summer tourists. Well-fortified against the cold, we paddled back out to lonesome Kāholo, the only anchor light in the anchorage.

Leaving Coupeville early, we had a serene reach south in calm water, all alone, jibing back and forth across Possession Sound under an asymmetrical spinnaker. It was challenging sailing in shifting winds, amid evergreen-­covered islands down Whidbey, the second-longest island in the United States, after New York’s Long Island.

The wind began to build as we neared the bottom of Whidbey. The helm felt lively. Somewhere around freezing, the wind sent a chill right through me. Adding another puffy jacket at the helm, I was quite comfortable but looked like the Michelin Man.

We blew right past the mooring I’d had in mind for the end of the short winter day, not to mention the alternate destinations I’d marked off in case the weather or the gear failed to cooperate. This was no ordinary sail, and we were having too much fun. We continued south toward Seattle.

Passing the southern tip of Whidbey Island, we sailed into the comparatively open water of Admiralty Inlet. Both the seas and the wind began to build. Now we were reaching at 12 knots with more than 20 knots of apparent wind. This was the upper limit for the spinnaker. The boat was ­handling well, but I could feel the rudder loading up as the boat leapt through the following seas. Rounding up in this wind with the spinnaker would mean taking it down in pieces. Breaking seas to windward alerted me that the wind was still building in the exposed waters of Admiralty Inlet. As the saying goes, any fool can put up a sail, but it takes a sailor to know when to take one down—and I’d ­apparently left it a bit late.

“Tracy!” I called out. “We need to get that spinnaker down. Now!” 

As Tracy hustled forward, I brought the boat downwind to hide the spinnaker behind the main. Tracy tried to douse the sail, but the sock refused to come down. The spinnaker sock lines had become tangled after so many jibes. I managed to balance the boat on a deep reach, with the seas slewing her around and the spinnaker flailing behind the main. I set the autopilot, praying we wouldn’t wrap the sail around the forestay, and jumped forward to help. We managed to untangle the lines while the autopilot miraculously kept us safely off the wind. The sock ­finally slid over the unruly beast and we dropped the sail to the deck with a sigh of relief. After that battle, we were no longer cold. The wind increased to the point to where the working jib was now plenty of sail, and we surfed south to Port Blakely, just across Puget Sound from Seattle on Bainbridge Island.

We arrived as the sun set and the lights of Seattle came alive in a purple sky. We could see the huge marinas of Elliott and Shilshole bays, housing thousands of boats. Yet we were alone, swinging at anchor in a quiet cove at the end of a perfect weekend sailing day. Finally, one other sailboat joined us: a singlehander on his 30-foot Wauquiez. 

With the setting sun, temperatures dipped well below freezing. Luckily, we had thick down comforters on the bunks to keep us warm. In the morning, I found water pooling on the floorboards, something no captain wants to see. Assuming we had a freshwater leak in one of the pressurized lines, I pulled off panels to reveal the hullsides. They were running with water. In freezing temperatures, comparatively warm moist air inside the cabin condenses on the cold hull of the boat “like a cold can of soda on a hot day,” as one sailor described it. I immediately invested in a dehumidifier for use at the dock. The proper solution while underway would, of course, be a diesel heating system. 

The northerlies were still blowing the next day, and we raised the spinnaker again, doing an outside jibe back and forth down serpentine Colvos Passage to Gig Harbor. For an outside jibe, I bring the boat directly downwind, jibe the main to put the boat wing on wing, and then completely release the working spinnaker sheet, letting the spinnaker flag in front of the boat. I then turn the boat through the wind, onto the new tack, and haul in the leeward spinnaker sheet, which is led around the bow on the outside. I can do this singlehanded, and it works like a charm as long as the sheets don’t get snagged on anything. Sadly, they often do, which requires a trip to the foredeck to unsnag them.

Gig Harbor was where we’d planned to meet the team from Iverson’s Canvas. A lively harbor town shadowed by Mount Rainier—with several marinas, a fishing fleet, a strong paddling scene, and lots of maritime history—Gig Harbor was named in the 1800s for Capt. Wilson’s gig, or rowboat, brought into the narrow entrance for shelter. The town is home to Gig Harbor Boat Works, which builds traditional gigs from modern materials.

It was amazing to watch Kyle and Mike, two guys from Iverson’s. They installed custom, large-diameter stainless, and patterned the entire dodger and Bimini top with plastic sheeting, all in a day. They said it would be two weeks for me to receive the dodger and Bimini top, but they were back a day early. The new dodger transformed the cockpit, with better visibility and clear windows. It felt as though I’d been upgraded to an ocean-view home after cowering under an old tent for years. It wasn’t cheap, but it was money well spent.

As luck would have it, sailing north back up Puget Sound was also a downwind run. Southeasterlies are quite common in winter, often associated with the approach of a low-pressure system. This was exactly the case I encountered: An approaching low was sending me 15-knot southeasterlies. I jibed back and forth up the sound, this time singlehanding because Tracy had flown back to Hawaii. Often, I would tangle the sheets on some obstacle on deck or on the anchor, and I’d need to hustle forward to free it. On my last jibe across Admiralty Inlet, on a layline for Port Townsend, I noticed the unmistakable T-shaped mast of a submarine steaming at me en route to the naval yard at Bremerton. Two oceangoing tugs and two US Coast Guard vessels were in escort. Soon, the Coast Guard politely hailed me: “Sailing vessel Kāholo, I see that you are making tracks for Marrowstone Point. We request that you keep as close as you feel safe to the shore. We will be turning right, into your path.” Good thing I was on a layline, with good speed, and didn’t plan another jibe. The consequences of something going wrong were too great.

An old friend, veteran bluewater sailing instructor John Neal with Mahina Expeditions, met me at the dock at Port Townsend. He showed me around the bustling boatyards and introduced me to his favorite sailmaker, Port Townsend Sails, and riggers, Port Townsend Rigging. These are family operations where attention to detail and craftsmanship are the rule. John says that he can get 50,000 to 55,000 miles (two circumnavigations) on a single main and jib built by the craftspeople at Port Townsend Sails, who, by the way, are all women. 

I set out on foot to see the boatyards at Port Townsend, the premier wooden-boat building and repair region on the West Coast. It’s a dynamic place where the next generation of shipwrights learns traditional skills at places such as the Northwest School of Wooden BoatBuilding. I wandered around the yards, amazed at vessels like the 133-foot San Francisco bar pilot cutter Adventuress, built in 1913 and still sailing here. 

Port Townsend is famous for its annual wooden-boat show, but what seems to have escaped worldwide notice is that Kirsten Neuschäfer, the South African sailor who recently became the first woman to win the Golden Globe round-the-world race, sailed a Port Townsend boat: a 36-foot, 1988 fiberglass-hulled version of a traditional 1930s design built by Cape George Marine Works. Her boat was among only three boats to finish the grueling race without pause for repairs, and it survived 235 days at sea around the tempestuous Great Capes—and with Neuschäfer managing to rescue a skipper whose boat had sunk.

Continuing my stroll through Port Townsend on this cold, blustery afternoon, and seeing a small sign advertising “sails and canvas built and repaired” on an old wooden building in the harbor, I ducked into a shop called The Artful Sailor. Engulfed by the smell of tar, hemp and linseed oil, I found Emiliano Marino and Pami-Sue “Salty Sue” Alvarado practicing the ancient art of marlinspike seamanship. The late-afternoon light streaming in through the windows made it look like a scene from an old Dutch painting.

Only in Port Townsend could a sailor encounter a nuclear submarine, see a 1913 schooner and meet a couple practicing traditional marlinspike splicing, all in the same day.

Unfortunately, my luck ran out with the weather, and I sailed the 30 miles up to Deception Pass and to Kāholo’s La Conner slip in full foul-weather gear, in cold, drizzling rain and variable winds. The ending was a bit of a letdown, but overall, this had been an unforgettable voyage, precisely because it had happened in the dead of winter.

Not that I am planning any Shackleton-esque small-boat crossings in the Antarctic, but at least now I understand the beauty of a winter’s sail. Next on the my shopping list? A diesel heater.

Tor Johnson is an award-­winning photographer and writer who has shot 16 covers of CW, so far. He grew up sailing the world with his family.

The post A Winter’s Sail appeared first on Cruising World.

My wife, Kati, and I are among the million boaters who helped to make Florida the state with more registered boaters than any other in America. We’ve lived in Orlando for three decades, cruising our 50-foot schooner, Britannia, all around the sailing haven and beyond to the Bahamas. Florida really is a paradise for those of us who love to take to the water. For so many boaters, it can be hard to imagine living anywhere else.

But last year, Kati and I reached a pivotal moment: We needed a fresh start in a new place, even if it meant bidding adieu to all we held dear. 

So, we looked to the north. Yes, there were drawbacks to this idea. Venturing north would elongate the return trip to the enchanting Bahamas, a paradise we longed to frequent. We didn’t want the biting chill of winter to necessitate an entire wardrobe overhaul. Nor did we care to wrestle with the tedious task of winterizing our boat’s engine and generator each fall. We weren’t seeking wholesale change, but instead an adjustment; we still wanted to live in a haven that would allow us to sail Britannia year-round.

A nautical map of the Eastern Seaboard drew our attention to a vast expanse of water on the eastern shores of North Carolina—Pamlico Sound, accompanied by its slightly smaller northern sibling, Albemarle Sound. Intrigued by these alluring destinations, we embarked on a weeklong exploration.

The picturesque town of New Bern greeted us, its charming streets steeped in British and Colonial history, adorned with an array of delightful restaurants and three adjacent marinas. Nestled at the convergence of the Neuse and Trent rivers, the town would give us easy access to Pamlico Sound, which sprawls 60 miles in length and 20 miles in width—a vast playground for sailors, replete with winding rivers, meandering creeks and quaint waterfront towns. The mighty Pamlico River also beckons sailors, enabling navigation for 40 miles up to the town of Washington—­affectionately dubbed “Little Washington” by the locals.

Among the renowned destinations on the Outer Banks—guardians of Pamlico and Albemarle sounds—is the legendary Kittyhawk, where the Wright brothers took their first flight. Sailors too are familiar with the treacherous Diamond Shoals off Cape Hatteras. This entire part of the Atlantic coastline has earned the moniker “Graveyard of the Atlantic.”

Between the splendid realms of Pamlico and Albemarle sounds, Roanoke Island emerges. It’s where the first British settlers planted their feet in 1587, predating the Mayflower’s storied voyage by 32 years. Being natives of the United Kingdom, as we strolled through towns with stores called Ye Olde British Tea Shoppe, we felt an instant kinship with these once-­British colonies. Moreover, adorning the 150-mile stretch of the Outer Banks are some of America’s most pristine, untouched beaches—a true testament to nature’s majesty.

We also discovered a delightful oasis from Florida’s high marina fees in the form of city docks, which this part of the country generously offers to visiting boaters for a few blissful days. Aboard Britannia, we were saved from shelling out nightly sums ranging from $60 to $100. 

Then again, if we wanted marinas, Pamlico and Albemarle sounds had them: a dozen marinas within Pamlico Sound alone, each conveniently located a mere fraction of the 70-mile journey we used to undertake from Orlando to Cape Canaveral in Florida, sometimes just for a fleeting day of maritime pleasure. And marina prices here were a mere third of what we paid in Florida. 

We also chanced upon Fairfield Harbour on the Neuse River. It’s just south of New Bern, evoking images of a miniaturized Fort Lauderdale. Canal-style branches sprawl across the main lagoon, with an array of homes that have private docks and picturesque gardens. 

The allure proved ­irresistible for Kati and me. As self-­employed individuals—me freelancing as a boating writer, Kati operating her real estate company—we found ourselves with minimal hindrances to relocating to North Carolina. And this location would bring us 400 miles closer to our daughter and grandchildren near Charlotte.

Within Fairfield Harbour’s confines, two yacht clubs awaited our arrival, including Blackbeard Sailing Club and its marina. The warm embrace of the yachting community enveloped Britannia. In our short time exploring, we forged friendships with more fellow yachties than we ever did in Florida. 

In addition, the specter of falling prey to a catastrophic hurricane weighed far less heavily on our minds here. Hurricane Florence brushed the region in September 2018, causing severe flooding, but unlike in Florida, such occurrences were rare. We had gotten Britannia out of Florida before the devastating hit from Hurricane Ian in 2022, but even being unscathed, we thanked our lucky stars and considered the idea of a home base where such devastation is less likely to occur. North Carolina’s Pamlico Sound dances to the tune of ­prevailing winds, ebbing and flowing in response to their whims. During strong gusts, a surge of 3 feet might materialize—a mere trifle when compared with the dramatic tides of the Atlantic and the kind of storm surge that wipes out whole waterfronts along the Florida coast.

Our minds were made up. We listed our Florida house for sale, and a buyer materialized within a fortnight, sealing the deal in just five weeks. Our new abode is at Fairfield Harbour, nestled amid verdant woods—albeit without waterfront access or a private dock. The truth is, we couldn’t afford to be picky. But we can still dream and keep an eye on the local market.

After sailing Britannia northward to her new haven, I secured a sizable dock rental from the homeowners’ association. Our boat’s new home port is conveniently located within walking distance of our abode. The cost is a mere fraction of what we paid in Florida.

We’ve been here for a while now. During the winter, snowfall greeted us, a rare occurrence after years spent in Florida’s warm embrace. I relished the opportunity to join our grandchildren in building a snowman in our front yard—an experience that had been absent from our lives for far too long. Such simple pleasures only add to the wonderful feelings we have in our newfound coastal haven.

As of yet, we have embarked on only preliminary ventures into the sound, cautiously exploring the places we discovered during our earlier visits. Of course, we intend to explore more as we further settle into our new locale. From secluded anchorages to quaint waterfront towns, our journey through the Southern seas will undoubtedly be one for the annals—a tale of discovery, rejuvenation and the serendipitous sojourns of a Southern sailor.

If you too find yourself yearning for a respite from the unpredictable climes of the tropics and the frigid North, let the winds carry you to the pristine beaches of the Outer Banks, the enchanting shores of the Pamlico and Albemarle sounds, and the warmth of Southern hospitality.

We’ll be among the boaters waiting to greet you with a warm smile and local ­knowledge.

The post New Cruising Grounds: Switching Home Ports From Florida to North Carolina appeared first on Cruising World.

We were cruising  through one of Desolation Sound’s towering fjords when the wind hit 35 knots. This type of a headwind is to be expected in this part of British Columbia, and it made me glad that I was—for the first time in my life—exploring a region not aboard a sailboat but instead aboard a 53-foot Grand Banks trawler with twin 650 hp engines. The term “powering through” took on a whole new meaning.

I’ve enjoyed more than a few sailing adventures in my lifetime—not just racing America’s Cup boats, but also on expeditions to remote places including Antarctica, Cape Horn, Sable Island (off Nova Scotia) and Norway’s Svalbard. I’ve completed trans-Atlantic crossings on sailboats too. Now in my 70s, I decided to try a trawler charter with NW Explorations, which is based in Bellingham, Washington. Our crew included my wife, Janice, who has cruised extensively in Maine and on the Chesapeake; longtime friends David and Christy Elwell, from Florida, who had cruised this area twice before this trip; and Kitty Mountain, also from Florida, but a veteran Desolation Sound cruiser. We were all of similar age, and we all had ­experienced our share of health issues in recent years. Somehow, letting a reputable charter company do most of the planning and make sure the boat was in good working order seemed like a reasonable compromise this time around.

It’s hard to keep me away from a helm, and I particularly enjoyed the solitude of many hours spent running the trawler from the upper deck. The views are fantastic from this perch, with the mountains along Desolation Sound rising 5,000 feet straight up out of the water. I thought about how, when the wind was exceedingly light, it would have been difficult to make progress under sail. Instead, we cruised onward at 9 knots, burning 6 ­gallons of fuel per hour. There was no hurry. We were having too much fun.

Desolation Sound is surprising in so many ways. Often, we would find a suitable cove to anchor, only to discover that the depth next to the shore was 600 feet. We’d have to look elsewhere or tie up to a few trees or rocks. And although the water was deep, it was surprisingly warm during our September cruise. The water was also, often, ours alone, with few other boats around.  

It’s counterintuitive that it could be so (relatively) easy to get to a place so remote, but that’s precisely what the five of us—a perfect-size crew for a trawler this size—had done. We had picked up the boat from the charter base in Bellingham and then cruised over to Port Sidney, Canada, to complete the immigration and customs process for Canada. The New York Yacht Club had organized a few rendezvous of which we took advantage (it’s always fun to compare notes with the crews aboard other yachts), and we were far from the only out-of-towners who were awestruck by the scenery.

Desolation Sound’s remoteness also gave us a liberating break from internet and cellphone service. We stayed busy with hikes, reading, and in-depth conversations about world affairs, the economy, and our grandchildren. We played spirited nightly games, took occasional naps, and focused on some of my favorite things: navigating and steering. The boat had an autopilot, but I like having my hands on the wheel and my eyes all around. Every few miles, an interesting sight or object would appear: a pod of whales, tidal rips, the ever-changing shoreline. The farther north we sailed, away from the impressive waterfront homes of Vancouver and the San Juan Islands, the more remote the scenery got.

After we anchored each afternoon, we enjoyed dinghy trips where we found all kinds of nifty things. We poked our bow into small coves, intriguing creeks, marshes and lagoons. We went ashore and worked our way through thick brush. Climbing was hard work, as was walking along the rocky coastline. We never saw bears or cougars, but we did see fascinating birds in the skies. The osprey clutches a fish with its face into the wind, making flight easier. Who knew?

Two cruising guidebooks were particularly helpful: Desolation Sound & the Discovery Islands by Anne and Laurence Yeadon-Jones, and Cruising Guide to British Columbia Vol. 2: Desolation Sound and the Discovery Islands by Bill Wolferstan. As a rule, the authors ­caution mariners to be mindful of tidal rip currents between islands. They’re correct. A few times, it was nice to be able to power up the engines and motor through passages that would have been challenging under sail. All kinds of boaters embrace the challenge, though; we encountered several flotillas of kayaks, including on one of the windy, rainy, chilly days. They waved happily as we steamed past.

I enjoyed Prideaux Haven, a scenic, protected cove that’s crowded during the summer months but had just eight boats scattered around on the day we arrived. The entrance is narrow and shallow, with Mount Denman off in the distance at about 6,500 feet high. For a (brief) minute, I thought we should attempt to scale the peak. The tidal range was about 18 feet, which meant anchoring with care. In one cove, we looked for the remains of an indigenous peoples’ village. We found only rocks, shells and sand, but it was fun to look around.

A few times, it was nice to be able to power up the engines and motor through passages that would have been challenging under sail.

At other spots, we encountered the fishing and logging industries that dominate this region. Signs ask mariners to reduce speed when passing the fish traps and working zones. On Toba Inlet, we watched a ground crew cut trees while a helicopter hovered over the trunks and grasped them with a heavy-duty clamp. At times, two or three trunks were hoisted together. They were moving 60 to 80 trunks per hour.

We followed the advice of the guidebooks at the Yuculta Rapids, a stretch of water with fast-moving currents at the northern end of Desolation Sound. The books strongly suggest transiting during periods of slack water; we experienced fierce rapids about one hour after slack water. Whirlpools, steep and choppy waves, and overfalls were evident as we motored through. Dent Island had a ­seating area where you could watch the churning rapids. We had a great dinner there, and, the next morning, a full ­breakfast before continuing on our expedition.  

I had to smile at some of the waterway names. Two of my favorites were the Hole in the Wall passage, which is a small opening connecting the Okisollo Channel to the Calm Channel, and the One and Only Inlet.

Along the Toba Inlet, we found ancient images of land animals and a sea serpent painted on the shoreline rocks. Equally as mesmerizing was a nearby 150-foot waterfall near picnic benches. One scene was more spectacular than the next.   

At one small general store, I found ­candy bars. My plan was to have one treat per day. The next afternoon, behind the wheel, I was enjoying my 3 Musketeers when the rest of the crew started asking, “Where’s mine?” I took some heat for the next few days, until we came across another general store where I was able to secure a larger supply, along with Raisin Bran cereal for one of our crew who loves it.

We also took comfort in our trawler’s solid hardtop and upper-deck chairs. I had to smile, remembering how, when I was 6 years old, I used to sit on the side of a small boat and marvel at the water gurgling alongside the hull. Here on Desolation Sound, I was still marveling at the water passing by. This instinct to appreciate the view has never left me, no matter whether I’ve been racing on the Irish Sea or from Rhode Island to Bermuda. I thought about my first sighting of the Antarctic peninsula with ice-covered peaks jutting into the sky, the surprising beauty of the Mediterranean, and the lush beauty of the Caribbean. The size of Chesapeake Bay is surprising, as are the endless destinations on the waters of New England. 

I have enjoyed all of it. What a nice life we have, being on the water. A few days after our expedition on Desolation Sound, I started to wonder, What’s next? 

CW editor-at-large and award-winning writer Gary Jobson is a Hall of Fame sailor.

The post Switching Gears: Exploring British Columbia on a Grand Banks Trawler appeared first on Cruising World.

Aaron Maynard owns an electric-­bike shop in Myrtle Beach, South Carolina, where a customer came in one day seeking a folding bike. 

“I asked him specifically why he wanted a folding bike because we sell many models,” Maynard says. “He said that he and his wife were going to sell their house and their belongings, and move onto a sailboat for a few years. After he left, I looked up ‘45-foot sailboat’ online. What I saw totally enthralled me. I began researching boats nonstop. I ordered a catalog from The Moorings and read it from cover to cover. In the back of the catalog, there was information about learning to sail.”

The next day, Maynard called Offshore Sailing School and signed up himself and his wife, Michele, for a certification class. They had never set foot on a sailboat when they attended the Offshore Sailing School at the South Seas Island Resort on Captiva Island, Florida, in 2018, joining the increasingly large ranks of people who are taking certification courses either to learn the basics or to gain advanced skills.

And make no mistake: It’s far from just newbies like the Maynards signing up for classes these days. For boat ­owners, some insurance companies require sailing certifications, and some charter companies have tightened up certification ­requirements for bareboat sailing as well. 

John Gaston was an experienced sailor and boat owner who had completed basic and intermediate cruising certification courses in Canada. He was looking for advanced cruising certification when he came across Barefoot Offshore Sailing School in St. Vincent and the Grenadines. He knew the school’s instructor, Rob McLean, who was associated with the courses in Ontario. Gaston signed up and completed his Sail Canada Advanced and Offshore courses in the southern Caribbean.

“I find that taking sailing courses provides excellent training to prepare for situations and response options,” he says. “I would rather learn from other people’s training and experience because you don’t know what you don’t know. A sailing course tends to be a safe and controlled environment.”

Taking the classes helped the Maynards and Gaston live their sailing dreams. The Maynards went on to complete multiple certifications, purchased a yacht and placed it in a BVI charter fleet, and have chartered 14 times over the years. They also bought a boat that they keep closer to home. Gaston recently completed an offshore sail-training trans-Atlantic crossing. 

Class Is In

No matter what sailing interests students have these days, there are classes available to help them achieve their goals. The American Sailing Association has certified close to 600,000 sailors at more than 400 sailing schools around the globe. 

Jonathan Payne, executive director of ASA, says that he sees two common paths in ASA sailing education. “One, someone takes in interest in local sailing courses. They make a long-term commitment to learn at a sailing school near where they live and attend weekend classes,” Payne says. This typically takes six weeks.

The second path, he says, is a ­weeklong destination school. “This is a full-­immersion, intensive course where students do a fair amount of study before arriving,” he says. “Once they are there, they are in class and running maneuvers sunup to sundown. The skill-building happens on the water.”

Of the two paths, the sailor who studies locally over a longer period might build a broader base of knowledge, while the other might be looking for a deep dive into the aspects of chartering. “A student in a course stretched out over six weeks might learn more about sail trim and sail theory, whereas someone on board a boat 24 hours a day might learn more about seamanship, bilges, and troubleshooting the engine,” he says. “There are certain things that happen on the water when you’re living on a boat. You have the opportunity to learn ­problem-solving in the moment.”

For the ASA local courses, Basic Keelboat Sailing (ASA 101) teaches skills inside a marina. Basic Coastal Cruising (ASA 103) takes the student outside the marina, and up and down the coast. Bareboat Cruising (ASA 104) is required to charter a boat.

“You can learn to sail in Colorado on your weekends, or sign up for a charter yacht in Greece,” Payne says. “There are a lot of options.”

US Sailing, the governing body for the sport of sailing in the United States, offers similar building-block tracks: Basic Keelboat, Basic Cruising and Bareboat Cruising.

Doris and Steve Colgate, founders of US Sailing-certified Offshore Sailing School, come from a racing background and have more than 160,000 graduates in over 60 years of teaching. Offshore offers one-week training courses in Florida and the British Virgin Islands, where students earn certifications for boats up to 50 feet. 

Students attend for a variety of reasons, according to Beth Oliver, vice president and director of sales and marketing. Some are new to sailing. Others are veteran sailors who want to experience the BVI. “These are people who either want to charter on their own, or who are considering purchasing a yacht and living aboard,” Oliver says. “They’re adventure-seekers with an active lifestyle, and want to share this enthusiasm with like-minded people. Many of our students are highly educated professionals, so continual learning is important to them. They like to share their skills with family and friends. Many want to pass on the sailing lifestyle to their children and grandchildren as a sort of legacy.”

 For those who want to charter, Offshore offers a combination course: Fast Track to Cruising. “We like to say that we can take you from your couch to the captain’s chair in one week,” Oliver says. Textbooks are sent in advance, and students arrive at class prepared to learn.

Offshore is the official sailing school of The Moorings, one of the world’s largest charter companies. The Moorings offers Offshore Sailing School courses in the BVI and Royal Yachting Association courses in the Mediterranean, according to Amanda Kurland, charter sales representative for The Moorings and Sunsail. These sister companies offer several levels of courses in multiple places. Sunsail has destination sailing schools in the United Kingdom, Croatia, Greece, Australia and Grenada.

Some people do the training because they want to purchase their own boat when they retire, Kurland says. Others are jumping from lake sailing to ocean ­sailing. Still others have the goal to ­charter a bareboat.

Blue Water Sailing School, an ­ASA-certified school in Fort Lauderdale, Florida, offers destination sail ­training charters closer to home. These are seven-day liveaboard courses where the vessels anchor out at night. Classes are available in Florida, Rhode Island, the Virgin Islands and the Bahamas. 

Blue Water owner David Pyle says that he also finds two basic groups of people looking for sail training: those who want to go cruising on their own boat someday and those who want to charter. “We try to get students to a point where they’re comfortable, confident and safe on a boat,” Pyle says. “It’s kind of like getting a pilot’s license to fly a small plane. You can get the training and certification, but of course you want to be safe and competent before you fly a plane on your own.”

Pyle says that approximately 15 to 20 percent of basic-level students return later for advanced courses. “We get a lot of people who have this goal to purchase their own boat,” he says. “They want to see if this is for them. I was just talking to a couple from Nebraska. They’ve never sailed, and they’re interested in finding out if this is for them. This is not uncommon.”

Pyle and Oliver agree that the most challenging aspect for students is often the amount of material they need to learn. Most students are also fairly anxious when it comes to docking. “Students who have been away from testing for a while might get nervous about the written-test ­component, but our instructors determine each student’s learning levels and preferences, and work with them individually, quizzing everyone each day on topics, so most are very comfortable by the time they take the written tests,” Oliver says.

There’s a lot of repetition and refreshing as the course goes along. Some students fear that they lack the physical strength for sailing work, but the sailboats have equipment such as winches to assist the student with maneuvers. Other students have a general fear of the water and ­seasickness, but most of that can be overcome with time on the boat.

Pyle says that it’s not uncommon to work with sailors who have had smaller boats, such as a 25-foot boat on a lake, but now want to go coastal sailing on a 40-foot monohull or offshore sailing on a 50-foot catamaran.

West Coast Multihulls in San Diego runs a sailing school with training on multihulls. Students who complete AS 101, 103 and 104 can take ASA 114: Cruising Catamaran Certification. It’s a five-day liveaboard class offered around Catalina Island and in the Sea of Cortez.

“We are catamaran experts with the largest sailing catamaran fleet on the West Coast,” says Guinevere King, general manager at West Coast Multihulls. “People come to our school to learn how to sail catamarans and experience the liveaboard cruising lifestyle in Southern California and in the Sea of Cortez.”

Most students want to get ASA 114 certifications while building their sailing resumes so that they can bareboat charter. “We also have a large percentage of our students who are looking to buy a catamaran and cruise the world with family and friends.”

 West Coast Multihulls also offers ASA 105 and 106 advanced courses for experienced sailors. The company recently added ASA 107 and 108, which cover celestial navigation and passagemaking.

“Our instructors share their knowledge and expertise with their students in a supportive environment,” Kurland says. “Our students gain confidence and invaluable real-world experience on board, which you can’t replicate by watching a YouTube video.” 

Barefoot Offshore Sailing School ­instructor McClean says that because there are so many levels and types of courses available, he doesn’t see a typical student but rather a thread that links them all. It’s people who want to sail, who want to live on a boat and learn for a week, who want to go offshore.

“Fifteen percent of our students are new to sailing,” he says. “Forty to 50 percent have already taken an initial course and are there to advance their skills.” The school welcomes all levels, he says, “but we do encourage people to take that first level at home. Someone can get far more out of their investment if they can learn the basics of tacking and jibing before coming to the Grenadines. It’s an ideal location for learning. You’re exposed to 8- to 15-knot winds, waves offshore off the islands, and a guaranteed variety of good winds.”

McClean says that the most important skill, in any context, is ensuring the safety of the crew and skipper. Other tough skills for students include navigating in ­unfamiliar waters, understanding weather, and anchoring at night. “Probably the most challenging [skill] we teach is crew-overboard drills,” he says, adding that students practice in multiple circumstances at multiple times. “If you’re not confident on all points of sail and you can’t manage a beam reach, then you need training and practice.”

After the introductory and ­intermediate courses, some students apply for advanced courses, including sailing at night. Some want to learn offshore sailing on a trans-Atlantic course. “We have a discussion with them to verify that this a good match for them,” McClean says. “The last thing they want is to wake up and find that this is the last place they want to be.” 

Award-winning journalist Theresa Nicholson is CW’s senior editor.

The post Back to School: Sailing Education Benefits Everyone From Beginners to Offshore Racers appeared first on Cruising World.

“willie, call me as soon as you can. i bought a boat. I haven’t seen it yet. It’s in the middle of Florida. We have to get it out of the boatyard by Monday.” 

When I received the voicemail, I was racing a Melges 24 regatta in Miami, and I knew adventure was brewing. My father-in-law, Chris, had started with casual boat browsing online and progressed to the sight-unseen purchase of La Reine, a 23-year-old Beneteau 381. In the process, he had set in motion a journey that would take my wife, Kim, and me on a 50-day, ­1,000-nautical-mile shotgun journey into the unknown. 

Starting with getting the boat off the hard for him within three days.

Two days later, I got my first sight of the boatyard where La Reine was waiting. Row upon row of deserted boats covered in various shades of mossy growth stretched as far as I could see. Imagination turned to panic as I drove past the first derelict hulls and pulled through the front gate.

As I entered the boatyard, heads popped out of companionways covered in fiberglass dust and paint. The boats in this part of the yard were notably more seaworthy, and a ragtag crowd was lovingly working on them.  

La Reine had a fresh coat of paint that made her shine, and a suite of new electronics gave her a modern feel. As a professional racer who has seen my share of collisions and repairs, I was very aware that the shiny new cosmetics might mask something far more daunting. I pushed the possibilities from my mind and set to work. 

The Caloosahatchee River makes up the western stretch of the Okeechobee Waterway, which connects the tranquil Gulf waters of Fort Myers to the Atlantic Seaboard at Port St. Lucie. We had not yet been able to secure a reservation in a marina on either coastline, so the plan was to take the boat a few miles downriver toward Fort Myers, and then leave her in Port LaBelle Marina to buy ourselves enough time to install safety gear and make a game plan.

That afternoon, one other boat was ceremoniously hoisted from its resting place in the yard in preparation for an adventure at sea. The excited young couple had spent the past two years on the hard fixing leaks, working on the engine, refitting plumbing, and everything in between. Briefly, the thought crossed my mind that La Reine should spend a few more months in the yard to go through all the systems, but it was too late for that. Whatever issues the new paint hid would be revealed soon enough.

After a three-hour round-trip drive to Fort Myers to acquire provisions for my first night on the boat, I returned to find that the stove wouldn’t light, so my quesadilla dinner became a cheese and tomato wrap. After dinner, I discovered that the toilet wouldn’t flush, thankfully in time to head up to the marina bathrooms.

Kim arrived early the next morning. After a pit stop to ­purchase parts, we started up the diesel on the first try. Our adventure was underway.

The first day was smooth motoring. Kim navigated the canal, and I watched YouTube videos to learn how to dissect the plumbing. As I wrapped up installation of a new pump and valve, we arrived at our first lock. The friendly lock operator walked us through the procedure, and the conditions were calm, making the process easy. When we were ready, the back gate closed, the front gate cracked open and dropped the water level 14 feet, and we were on to the next section of canal.

At Port LaBelle that evening, we were greeted by an alligator floating lazily past the entrance. We cut the drone of the diesel, so the only sounds left were nature: plentiful bird life and the distant moos of cows. It was the quintessential Southern evening. We still didn’t know where we were headed, but for the next few weeks, this would become our launch pad for the projects needed to make it to the ocean, and whatever lay beyond. 

We had only a few short days in Port LaBelle before I had to head back to work for a week, and Kim had a trip planned with friends. We crammed in as many projects as possible, with the expectation that we’d be headed to the ocean the next time we saw the boat.

When we returned to Port LaBelle, Chris had settled on a summer marina at Jekyll Island, Georgia. Meanwhile, Kim and I were plotting a one-month detour through the Bahamas. We would head east on the Okeechobee Waterway, then south to Miami and up through the Bahamas, then to Georgia. We didn’t have any marina reservations, but we felt that there was no better way to get to the top of the waiting list than to show up.

As soon as Kim arrived, we transferred a mountain of boxes we’d ordered online from the marina office onto the boat, and we bid farewell to Port LaBelle. With a nice following wind, we unfurled the jib for the first time and retraced our tracks from only a week before.

After about an hour, we arrived back at the lock that we had previously dropped down and prepared to float back up. “Ready?” came the voice of the operator. We thought we were.

As the back gate closed, I noticed that the fenders were slightly too far apart. The freshly painted rail of La Reine came to rest just inches from the cement wall as the front gate opened and water rushed into the lock. The boat seesawed at the mercy of the floodwaters. 

With my gaze fixed on the tiny gap between the rail and the wall, I wrestled with the dock line, fighting to avoid grinding off the fresh coat of paint. Minutes seemed like hours, but eventually, the water calmed and the boat came to rest. Miraculously, the rail was unscratched. 

For the rest of that afternoon, we motored lazily up the canal, past Glades Boat Storage and up the river to Moore Haven, where we spent the night on the city dock.

The morning was full of beauty, with golden sunlight pouring down on swampy vegetation and animal life. Alligators, turtles, lizards, and birds of all varieties seemed to wake with the sun and escort us down the next stretch of the ditch. 

By late morning, we passed through Clewiston and reached the entrance to Lake Okeechobee, where we set a course through the narrow channel. By noon, land slipped from sight and the wind built to the midteens. Our jib was deployed, and our adventure seemed to be in full force.

Kim was at the helm when the steady, rhythmic knocking of the diesel began to fade. At first, I thought one of us had bumped the throttle, but power quickly faded to an idle thrust. I spend a lot of time around outboard engines in my job as an Olympic sailing coach, but the diesel was a new beast. This felt like a gas issue, but the gauge read three-quarters full.

Kim turned us head-to-wind while I hoisted the main and cut the engine. The wind was puffing at nearly 20 knots and, luckily, carried us downwind toward the far lakeshore, but we knew we would need the engine to get through the lock on the far side. Kim drove while I went below to put on my mechanic’s cap.

After about an hour, I had drained some sediment out of the fuel filters. I was cleaning out the air-intake manifold when Kim called down: “I can see the lock getting closer. The waves are getting bigger. What are we going to do?”

I poked my head back up. The channel markers for the lock were getting close. 

We cranked the engine, throttled up, and La Reine plowed forward. 

“Sails down and fingers crossed—all we can do now is hope that it doesn’t die again,” Kim said with a worried look. 

We hailed the lock operator. The wind was now blowing a steady 20 with a lumbering, lumpy chop. The lock operator came on the VHF radio: “Conditions are rough, but it’s not getting any better. Let’s get you through. When you get inside, let me close the gate before you go to the wall so that the chop can die down.”

If the engine died now, we’d have major problems. We carefully nosed into the lock, with the boat pitching wildly from the chop. 

“Be ready with a mobile fender in case I lose control,” I told Kim. 

As the gate swung closed behind us, the engine held, but even with full power, I was fighting hard to keep the boat under control. The bow swung left, then right, at the mercy of the wind, so I tried to keep the stern centered to buy enough time for the chop to subside. 

“That’s it,” came the voice of the lock operator. The chop was still big, but we were fully committed, so I took a deep breath, tried to relax, and waited patiently for the bow to swing. As the next puff took hold, the boat rotated 20 degrees, lining us up for a nice approach to the wall. I hit reverse, praying that the engine would hold just 60 seconds longer.

In the end, it was one of our smoothest lock passages. While the lock operator commented on our excellent boathandling, I told myself, Better lucky than good.

I started to relax as we exited the cement box into the ­tranquility of the canal on the other side, but no sooner had we passed the final gate than the bridge ahead stole my focus. This 49-foot railroad crossing controlled the navigational height east of Lake Okeechobee. 

We radioed the operator for a final check on water-level height. When we told him we were 48 feet tall, he replied, “Don’t quote me on this, but I think you’ll probably make it.”

The adrenaline took hold again.

Back at Port LaBelle, I had gone up the rig and measured that we should have a foot of clearance above our mast, but seeing the bridge in front of us, my imagination ran wild. I envisioned a westbound motorboat trying to squeeze through the bridge at the same time as us, with its wake bouncing us into the top of the bridge. We figured that every inch mattered, so, using a hammock, we rigged up a seat for Kim on the end of the boom. As I swung her out over the water, the boat heeled 5 degrees to starboard. I had calculated that this should buy us 6 extra inches of clearance.

We went as slowly as possible, with the hope that impact at these speeds might give us a chance to save the rig, but the ­approach was agonizing. Hanging over the water, Kim worried that she might have a date with an alligator if things went south. 

At the last moment, I threw the boat in neutral. As we glided smoothly through the crossing, I looked up. Was it just me, or was the antenna on top of the rig tickling the bottom of the bridge? No, just my imagination. Elation. We were through.

We laughed and smiled and felt like heroes. We had avoided the lengthy western route through the Keys, and the sun was shining.

We didn’t notice the first few raindrops. All afternoon, I had been tracking the cumulus development to the north, and while the fluffy white pillars had grown into thunderheads, the radar showed no sign of southern movement. While we’d been preoccupied with the lock and the bridge, though, the system had veered sharply. Within minutes, I found myself diving for my foul-weather gear in pelting rain.

No sooner was I dressed than the engine died again.

Kim rushed below to grab the windlass controller. The crackle of thunder and lightning in the distance was getting closer. I swung the bow head-to-wind in the lee of a thicket of trees and, with the last of our momentum, did my best to estimate the swing of the boat in the narrow canal. 

“Drop 20,” I called, glancing at the depth gauge. Kim put down 20 feet of chain as the boat started backward. 

With the anchor set, we scrambled below and closed the hatches to wait out the rest of the squall and continue working on the diesel. 

Later that evening, La Reine slipped down the glassy canal as the towering cumulus above the forest reflected golden oranges contrasting with ragged, dark grays. La Reine’s diesel, alive once again, buzzed gently under my feet. The air was still thick from the rain, but it was cool now that the storm had moved off into the distance, having washed away much of the sweat, grease and stress that marked our first big day of delivery.

As we pulled into a slip just before the final lock of the trip for the night, I was reminded that man plans and God laughs. Of all the scenarios I had run through in my head, the leeward shoreline lock with a dead engine had not been one of them.

The next day, we headed for the Atlantic. We geared up, ­tethered in, and headed out of Stuart in a beautiful 15-knot northerly for La Reine’s first true sailing test.

The first hour was all smiles. We surfed the waves, reaching and winging our way down the coast. Through the afternoon, the breeze built and more rolling waves began to make Kim feel sick, so we set a course for an inlet a few miles down the coast. Before we could make it to the calm water, however, we heard a popping noise, and looked up to find a large hole in the luff of the main. A seam of old stitching had given out, and rotten threads on either side looked ready to give way too.

The mainsail blowing out wasn’t something that we could have predicted, but as soon as it happened, we made the best of the situation. Kim took the helm and spun us into the wind while I reefed the main to the second reef point. This confined the hole in the sail to the folds of the reefed slab, allowing us to continue down the coast at a good pace as we motorsailed to Hillsboro Inlet at Pompano Beach.

For the next few days, the clear-blue Miami water replaced the murky green twists and turns of the Intracoastal Waterway, and we began to feel one step ahead. As we wound our way through the juxtaposition of wild nature and intensive urban ­development, we were able to secure a mooring ball, schedule a mechanic to service the engine, and book an appointment to have the boat sized for a Bimini top.

In the final stretch, we navigated intense Saturday traffic in Miami: lavish yachts, loud music, and crazy chop from ­reckless boaters. As we turned into the calm waters of Dinner Key Marina, sweet relief washed over us.

Champagne in hand, we video-chatted with Chris, telling him we’d made it and that La Reine was in one piece. We spent the rest of the evening reliving our endless snafus, laughing and smiling. It was amazing how much life we had lived in just four days.

What had we learned? No matter whether you order your boat new or find one online, plans will eventually fail. And when they do, the real adventure will begin. 

The post Sailing Across Florida: An Unexpected Adventure appeared first on Cruising World.

The mid-May sun was surprisingly hot as we spun into the wind, idled the engines, and hoisted the big roachy main aboard San Fredelo II, the Sunsail 404 catamaran that would be home for the next five days. Next, we rolled out the genoa and bore away to a beam reach, leaving provisioning chores, briefings, crew introductions and the Marina Agana astern. 

Sailing, at last—in Croatia. A longtime entry on the proverbial bucket list was about to be scratched off as my sailing pal and trip organizer, Josie Tucci, vice president of marketing at Sunsail, steered us eastward and out of the narrow bay toward open water dotted with islands. Near the helm, her brother, Jason, and I trimmed in the sheets and tidied up as we began making way. To port, I could see cars on the coastal highway, headed north from the international airport in Split. To starboard, the rocky, brush-covered shoreline rose to meet a sky that was fairy-tale blue. Already, my colleague, photographer and drone junkie Jon Whittle was snapping away. How could he not? The sights were otherworldly in this centuries-old corner of the Adriatic Sea.

Around us that Sunday morning, the crews aboard nine Sunsail monohulls were going through similar drills, as one by one they raised sails and pointed their bows toward Milna, on the island of Brač, the flotilla’s first-night destination, where a gin-and-tonic reception awaited us.

I’d never sailed in a flotilla before, but already, less than a day into it, I was enjoying the concept of exploring a new destination with a helping hand, if you will. Earlier that morning, after a buffet breakfast of eggs, sausages, fruits, and doughnuts at the marina’s restaurant, skippers, and crew gathered in a shady spot to meet Sunsail’s flotilla captain, Samantha “Sam” Algero; hostess Ellie Riccini; and “Drago,” the team engineer. This trio would be on hand to assist and advise 24/7. When it was time to go, they’d be the ones handing us our dock lines. And when we arrived at a new location, their boat, Hvar 1, would already be tied up. They’d be waiting to take stern lines as skippers nervously (at first, anyway) backed in to moor stern-to at each new village.

“Slow is pro,” Sam reminded us frequently the first few landings.

Ellie too dispensed practical info. “Keep the boats tidy,” she urged. “A tidy boat is a safer boat.” And, “Beware the sea urchins.”

At that first briefing, Sam and Ellie outlined the week ahead: daily skipper meetings at 0900, lunch where you like, and each evening a different destination with a suggested time of arrival. At night, there were organized events to attend—or not. Wednesday, we were free to sail wherever we liked, so long as we all regrouped in time for dinner on Thursday.

They went over the fine points of Lateral Navigation System A (red and green buoys are opposite where they would be in the United States), safety issues, and local weather to watch. The bura is a gusty northeast wind that brings clear conditions. The jugo: southeast breezes with rain. The maestral northwesterlies tend to build in the afternoon. 

And these words of caution: “If you didn’t eat it, don’t flush it.” Holding tanks were to be emptied 2 miles offshore, and there was a 100-euro fee to fix a clogged head.

Alrighty, then. Duly warned.

But best of all, their review of the charts greatly ­simplified finding the Croatian place names that were difficult to ­pronounce, tough to understand, and even harder to spell.

Off to the Islands

Josie, Jason and I had spent Saturday afternoon provisioning at the nearby Tommy’s market. For a few coins, you could borrow a shopping cart to deliver groceries to the boat. We stocked up on lunch meat and breakfast fare, Croatian wine, and Ožujsko, a local beer. That evening, we had dinner at the marina and sat on San Fredelo’s tramp watching the moon rise over the opposite shore. The water was still, and the reflection of the square stone tower at the head of the harbor was crystal-clear.

Sunday turned out to be a perfect day to regain our sea legs, with a northerly breeze in the midteens sending us on our way. We stopped for a late lunch and anchored in the pretty little harbor at Stomorska, on Šolta, a point that was about halfway into our 18-nautical-mile sail. The anchorage allowed an imposing view of the towering mountains that rise above metropolitan Split. Ashore, a handful of fishing boats sat idle, and we saw but a few folks moving about amid the distinctive white villas with red-tile roofs.

From there, it was an easy run to Milna and the Marina Vlaška. As Josie backed the cat toward the quay, Jason and I stood on either transom with boat hooks in hand. We handed our stern lines ashore, and the Sunsail team held up bowlines for us to grab and take forward. The ropes are sunk when not in use, and are led from shore to anchors in deeper water. It was an amazingly drama-free operation.

Once we were settled, we grabbed swimsuits and found a nearby rock from which to jump. The seawater was cool but refreshing, making a hot shower at the marina afterward feel all that much better. Then we headed up the hill, past olive trees and stone terraces, to claim our gin-and-tonics, and to chat with other crews as they came and went.

At sunset, we walked a mile or so along the shore road into town. On the way, we passed a street vendor and stopped to buy four garishly colored Croatia ball caps that quickly became our team hats. In the town center, a large, weathered stone church was lit up, along with other ages-old buildings. Behind them, we spotted more steeples draped in light. We found an open table at a small pizzeria and washed down our slices with tasty local wine.

Of course, we posed for photos with the colorful, whimsical ice-cream-cone statue we passed on the way back to the boat.

Relic of War

A look at the charts reveals that along this part of the Croatian coast, long, thin, mountainous islands run roughly west to east from the open Adriatic, as though some ancient creature drew fingers though terra firma, allowing the sea to run in between.

On Monday, we didn’t have a lot of wind as we motored out of Milna and turned southwest to navigate the channel between Šolta and Brač, and turned again southeast to follow the coast. We passed numerous marine farms and inviting anchorages, but we’d already decided that our lunch-stop destination would be a small bay a few miles south, where a submarine base dating back to when the country was part of Yugoslavia is carved into the hillside. Once we’d found the cove and anchored, we launched our inflatable and took a ride inside the long, narrow tunnel once used by naval vessels to avoid detection. Rather than seeing warships, we found cool relief from the sun-splashed bay. Today, fishermen use the rock-lined safe haven to tie up their skiffs. During our visit, there wasn’t a soul around. Instead, small birds darted about, their shrill chirps echoing off the rock walls.

The cove was quite protected. As a few others in the flotilla fleet arrived and dropped anchors, we took turns exploring on the two paddleboards we’d brought along. 

That afternoon, a lazy breeze picked up from the northwest, and San Fredelo ran before it as we headed for the harbor at Jelsa, on the island of Hvar, across a body of water marked on the chart as the Hvarski Kanal. After a morning of motoring, all aboard welcomed the sail, but the dead-downwind heading proved both crash-jibe prone and slow. Eventually, we kicked on the motor again to make the harbor in time for a 1600 tie-up. After all, wine and hors d’oeuvres at a waterside restaurant, organized by Sam and Ellie, awaited us. 

Jelsa lies near the midpoint of Hvar’s north shore. Its harbor is a relatively square body of water, protected by stone jetties. Wide, flat stone walkways around the waterfront give the place an open plaza-like feel. When we arrived, several flotilla boats were already tied stern-to, but Capt. Sam directed us to an open spot, and her crew scrounged up a plank for us to use as a passerelle. 

The restaurant, the iconically spelled Me and mrs Jones, was on the far side of the harbor. Our stroll there took us past palm trees and weathered stone buildings—some white, others a faded pinkish color. Inside the restaurant, the front room had been cleared out to make space for a table covered with wineglasses, carafes of red and white wine, and trays piled with appetizers made with anchovies, shrimp, and assorted meats and cheeses. Soon, the stone-block-lined room was packed. 

After an hour, the crowd thinned and the staff began setting tables for dinner. Jason and I took a half-empty carafe of red and sat at a table outside with a couple from the flotilla who were sailing aboard a Jeanneau 34. Steve was from England, Josephine from Hong Kong. Prior to the pandemic, these longtime friends would meet at various locations around the world for sailing vacations. This was their first time together since the global shutdown. They planned to keep the boat at the end of the week, and sail up and down the coast a bit longer. Like sailors everywhere, we talked about weather, memorable voyages and, of course, our current adventure, which they were finding to be quite social compared with their usual visits to quiet, remote anchorages.

As we were about to leave, a pair of women rode up on bikes and sat at the table next to us. They pointed to the road winding up the towering mountains that form a spine atop Hvar and said that they’d just come over them from the other side of the island. No wonder they were ready to sit down and quench their thirst.

That evening, we strolled up into the hillside town from the waterfront. The stone streets were polished smooth by centuries of foot traffic, the narrow lanes between buildings too tight for cars. The sounds and smells from the open-air Konoba Nono restaurant were irresistible. Its barbecue was excellent, and we topped it off with glasses of rakija travarica for dessert. The strong-tasting liquor, often made of plums and herbs, is a Croatian delicacy and must at least be sampled, in my humble opinion.

I say “sampled” because in abundance, it can lead to unexpected consequences. After dinner, Jason returned to the boat while Jon, Josie and I continued to explore. Our ramblings took us past age-old churches and through tight, twisting alleyways, past homes with laundry left out to dry in rocky courtyards. Eventually, our footsteps led us to a tavern, which led to Croatian beer and then more rakija. We were left spellbound by the sweet folk melodies that a woman named Anna and her male vocalist partner sang as they leaned against the bar, drinks in hand. When the bar closed, we lingered outside, talking with the singers. He had to work in the morning and said goodbye. Anna? Well, we followed her to the small bar she owns and sat talking until dawn, then went with her to watch the sunrise from a beach.

That’s the thing about a sailing trip to Croatia. The people are as warm and friendly as the islands are lovely. It was easy to strike up a conversation with just about anyone. Most Croatians we met spoke English. Every storekeeper had a smile. The owner of an olive shop, recommended by a waiter and contacted by phone one evening, agreed to open early the next morning so that we could buy delicacies to take with us. Strangers couldn’t wait to tell us why we had to visit their favorite spot. Everyone had one. It’s easy to fall for such charms.

Off On Our Own

It’s perhaps not surprising that we were the last boat off the quay Tuesday morning. Not to worry—we had just a 12-nautical-mile hop to the west along Hvar’s north coast to reach the protected bay off Stari Grad, one of the oldest towns in Europe. The little wind we had as we left Jelsa was on the nose, so we chose to motor instead of sail. It was yet another lovely little adventure on the water, complete with dolphins. Across the channel, the mountains on Brač were a patchwork of earth tones and greens, the hues of olive trees and gluhi bor, a black pine that covers the arid landscape. Ferries crisscrossed the channel, and we passed numerous small fishing boats and saw flocks of birds working the water roiled by baitballs off in the distance.

By 1430, we were tied up to yet another stone quay in a snug ­harbor surrounded by a bustling town. We moored just in front of the town’s municipal showers, which were handy. From there, Jon and I walked a half-mile or so along the quay to restock at a Tommy’s market, and then met the rest of our crew for a late lunch.

Back at the boat, we sat under the cockpit Bimini top in a feeble attempt to evade the stifling afternoon sun, and chatted with the crew aboard the flotilla boat moored next to San Fredelo. 

We dined ashore that evening at Nook Stari Grad, a restaurant recommended by a passerby. The woman waiting on us had ­recently returned from living in Rochester, New York, and we met another member of the waitstaff who’d been lured back from California. Both were tickled to be home. The Nook’s chicken curry was spicy, the beer was cold, and the open-air seating under an arbor of trees was absolutely delightful. We walked the long way back to the boat, through more narrow stone streets. On the ­waterfront, there wasn’t a ripple on the harbor, and even in the town center, the quiet was interrupted only by the occasional dog bark.

Wednesday was our free day, and a bura was forecast for the afternoon. After looking at the chart and cruising guide, we decided to sail southeast along the coast of Hvar and across the Pakleni Kanal to the island of Sveti Klement. 

We set sail as we left Stari Grad and tacked upwind around the western tip of Hvar. From there, we were able to bear away and reach down the middle of the channel between the two islands. Early on, the 10- to 12-knot breeze was perfect. But as the morning progressed, the wind clocked and turned gusty so that before long, the sea was covered with whitecaps. At the eastern end of Klement, we turned south and sailed through a marked channel that runs close to the island, and then doused sails as we spun to the west to motor a short way up the island’s south coast to Vinogradišće, a small, protected cove that’s home to Laganini Lounge bar & Fish house and a small mooring field just off its dock. After a swim, we headed ashore for lunch at a table overlooking the water, and watched two self-described influencers shoot photos of one another over glasses of bubbly. As we finished our dishes, a motorboat arrived to whisk them away, shooting selfies all the while.

We spent a lazy afternoon swimming off the boat and, before sunset, walked a short distance across Palmižana, where we caught a water taxi to old-town Hvar. The wind was still gusty, and it was a wet ride back across Pakleni Kanal but well worth the trip.

Hvar is a vibrant city, the largest on the island, with a long history of being a trading and cultural center. The city was part of the Venetian empire from the 13th to the 18th century, and a naval base as well, with an imposing fort above the waterfront.

As in the other towns we’d visited so far, we walked. From the harbor, we hiked up a seemingly endless flight of stairs toward the fort. Shops, hotels, restaurants, and residences lined the steps and stone alleyways that led off to either side from occasional landings. We found a small, rock-walled cafe where we ordered a tableful of appetizers rather than a full dinner: sausages, meats and cheeses, octopus, sardines and the like, along with olives, anchovies and grappa. Afterward, we walked some more. A plaque on a monastery we passed dated the stately white-stone building to 1472. In one shop, we spotted a merchant armed with a knife, standing behind a huge slab of prosciutto held upright on an iron stand. You bet we had him carve off slices to take back to the boat, along with a couple of bottles of cherry grappa. 

At 2130, with minutes to go before the last water taxi ­departed for Palmižana, we hustled back down flights of stairs to the waterfront, arriving at the dock with little time to spare. Over the course of the evening, the winds had died, and we had a lovely ride back to Klement, with the night sky ablaze with stars.

Last-Night Raft-Up

After a swim and coffee Thursday morning—and, how could I forget, spinach-and-tomato omelets—we motorsailed east along Klement’s south coast, winding through Soline Bay and the outcrops of rocks at the end of the island. From there, we reached northwest to Šolta and anchored in the bay at Tatinja—called Uvala Tatinja Lonely Paradise on the chart.

Lonely it was. There were only two other boats anchored there and just a couple of houses onshore. In front of us were centuries-­old stone terraces built into the hillside and groves of trees; ­behind us, nothing but the deep-blue Adriatic Sea and a cloudless, deep-blue sky overhead.

That night, we anchored stern-to on a rocky shore in Šešula, with the entire flotilla rafted together in front of a small restaurant. The bay was quite large, and we went exploring by dinghy, motoring alongside new friends Lawrence and Cathy in theirs. In a distant corner, we found a fish farm before turning back. In the afternoon, Sam and Ellie organized inflatable races, with two-person crews paddling their hearts out for bragging rights. 

Dinner that night was a group affair, and afterward, the party moved back to the boats, where the monohull crews gladly came to visit our big, roomy cat, helping us clinch Best Party Boat honors at the farewell dinner Friday evening.

The next morning, Josie, Jason and I walked along a coastal trail lined with flowering bushes and the occasional modest house, and came to a small village, Maslinica, where we found a working marina, a couple of shops, a spot serving breakfast, and a 20-foot-long yellow-submarine statue with photos of John, Paul, George and Ringo staring out of porthole-like circles on its side. It was a sleepy tourist town, and a sign near its center said that it had received numerous national tourism awards, including one in 2017 for being the best Authentic Coastal Destination.

On our return that morning to Marina Agana, we had the wind on our nose again, so we took our time motoring toward the mainland. We made a detour to visit the long, deep bay at Vinišće; the shore was built up with houses on one side and an industrial-looking pier on the other. Instead of stopping for lunch, we raised the main and sailed across to the open bay off Trogir, anchoring for a spell to eat and swim.

And then, at last, it was time to return to the marina where we had started. On the dock, once the boat was squared away and ­before we took a taxi ride into the hills for one last group ­gathering, I chatted with Bill Truswell, an Irishman in his 70s, who, with his wife and two sons, had enjoyed this week of ­flotilla-style sailing.

“Stress is something I’m no longer needing in life,” he said.

I couldn’t agree more. 

The post Setting Sail: Adriatic Adventures on a Flotilla Charter appeared first on Cruising World.

An autumn passage from the US East Coast to the Caribbean is one of sailing’s great adventures. Every fall, hundreds of sailing yachts make this voyage—alone, with a buddy boat, or in a rally. No matter which route you choose, it’s approximately 1,500 miles, taking eight days to two weeks of sailing time in the Atlantic, over the Gulf Stream, and through the Bermuda Triangle. There’s a high probability you’ll be hit with a 30-plus-knot cold front and a couple of squalls before you pick up the trade winds for a few of days of delightful beam-reach sailing into the islands. Here’s a look at three ways you can head south.

Option One: From Newport, South

Being from Maine, I used to sail down to Newport, Rhode Island, for the boat show in September, and then leave for Bermuda when the forecast was favorable. At that time of year, the weather windows are usually wide open. I’d keep an eye on the tropical weather and, if no storms were brewing, I’d leave, knowing I’d get to Bermuda in five days, before a hurricane could form and beat me there. 

More recently, I’ve taken to joining Hank Schmitt and other delivery captains on the North American Rally to the Caribbean, which departs from Newport in late October. Schmitt has been organizing the NARC Rally for the past 24 years and is planning on turning over the tiller to the Salty Dawg Sailing Association in 2024. 

This Newport departure leaves on northwest winds of 18 to 25 knots. With the wind astern, it’s 200 nautical miles—about 33 hours—to the Gulf Stream. Pick a waypoint on the north wall of the stream, west of the rhumb line. By the time you exit the stream 10 hours later, the 3-knot current will have swept you 30 miles east, putting you back on the rhumb line. With the stream behind you, it’s time for T-shirts and shorts. 

Bermuda is just 360 nautical miles ahead—two and a half days away. You’ll see Bermuda’s lights hours before landfall. The last time I made this trip, in 2021, we got there in three days and 20 hours, with winds no stronger than 25 knots all the way.

Wait in Bermuda a few days fixing stuff, reprovisioning, taking on fuel, socializing, enjoying the island, and resting up for the 850 miles from Bermuda to St. Maarten, or 950 miles to Antigua. Five to eight days in length, this second leg of the voyage will be a great deal more enjoyable. The worst is behind you.   

This stop in Bermuda is my ­preferred route, even if I depart from Chesapeake Bay.

Option Two: Departing the Chesapeake

Leaving from the Chesapeake means that the Gulf Stream is only 100 miles offshore. You’ll be across it within 24 hours. Don Street, the old guru of sailing, says that if you are already south and west of Newport, your best bet is to depart from the Chesapeake, or farther south. (Street’s first published article was advice on sailing south, 60 years ago in Yachting, September 1964.)

Leave on a northwest cold front, and you’ll have the wind abaft the beam for two or perhaps three days.

This popular route is a 1,500-nautical-­mile east-southeast arc out into the Atlantic before turning south. It’s a seven- to 12-day nonstop voyage, with two to six days of motoring through the Bermuda Triangle. While this route bypasses Bermuda, each year, a few boats stop there for fuel, rig or sail repair, or to just break up the long voyage.

Boats need to have fuel for at least five days of motoring, and food for three weeks. Each year, a few boats run into problems with steering, the rig, fuel or seasick crew, and they retreat. Better to be prepared.

If the weather has you bottled up in Hampton or Norfolk, Virginia, you can motor down the Intracoastal Waterway. The rule on the ICW is 63/6 (meaning a 63-foot mast height to get under the bridges and a 6-foot draft so that you don’t run aground). In three days, you’ll be in Beaufort, North Carolina, a wonderful town with three marinas. From there, the Gulf Stream is only 50 miles offshore. You’ll be across and into warmer weather in 15 hours, and then it’s a similar course as those departing from the Chesapeake.

From Beaufort, you can also meander farther down the ICW, or sail slightly offshore inside the Gulf Stream, ducking into ports when necessary, all the way to Florida. 

Once in Florida, you have your pick of departure ports: Fernandina, Palm Beach, Fort Lauderdale. In late November and December, watch the weather carefully. 

“When a good hard norther threatens, leave 24 hours before,” Street says. “Place a pound of butter on the main cabin table, head east-southeast until the butter melts, and then turn south. Then, head southeast, and you might actually arrive in St. Thomas on track all the way. These are the same sailing directions that have been given for probably 300 years.”

If the weather in the Bermuda Triangle is unfavorable for making the offshore voyage, there’s the Thornless Path. 

Option Three: The ThornLESS Path

If you are departing from anyplace in Florida, and if the winds in the Bermuda Triangle are nonexistent or contrary, then hopping down the Bahamian chain is an option. You can sail down the chain either outside to the east or through the chain itself. The latter requires stops to anchor each evening. Joan Conover, president of the Seven Seas Cruising Association, has sailed the Thornless Path a few times and favors it as a route south. Bruce Van Sant’s book The Gentleman’s Guide to Passages South maps out this route in detail.

The Turks and Caicos is a jumping-off spot for the slog south and east to the Dominican Republic, Puerto Rico, the Virgin Islands, and the Eastern Caribbean. Traditionally known as the “Thorny Passage,” it’s a windward bash against the trades, current and swells, but it can be done; just stay clear of Haiti. There’s a process that savvy skippers use of sailing at night along the coast of Hispaniola.

In the Dominican Republic, you’ll find the Caribbean of 50 years ago. YouTubers have posted videos on finding the ports of entry, crossing the Mona Passage, and understanding the route along the south coast of Puerto Rico. Noonsite.com has up-to-date information on port entry, marinas, services and restrictions.

Getting Ready

No matter which route you decide to take, the journey starts with planning and preparation. My pre-departure checklist is eight pages long. Here are a few things to consider.

The boat: Is it seaworthy, capable and ready? Is it designed and built for an offshore voyage, or for coastal cruising or racing? Inspect everything from stem to stern, masthead to keel, and hire a ­surveyor to catch things you’ll miss. Your insurance company might insist that you have a recent survey anyway. Get it done early so that you have time to make repairs. Be there to watch and ask questions. Also have a professional rigger and an experienced diesel mechanic do ­inspections. Grease the steering system, and tighten the bolts in the quadrant. Find and test the emergency tiller. Is the rig set up for offshore, with an inner stay on which to hoist a staysail, or a Solent stay? Can the boat be reefed and hove-to easily? Are the bilge pumps adequate? Is all the safety and person-overboard gear up to date? 

Supplies: You’ll need to carry enough fuel for five days (100 hours) of motoring, plus drinking water and provisions for three weeks. Remember to bring enough toilet paper. I forgot once. Had to turn back.

The crew: Have at least two or three seasoned sailors with you who don’t get seasick, can stand a solo watch, and know what to watch for. I find crew on sailopo​.com, which is free. Your insurance company might want to see résumés from you and each crewmember, and might insist that you hire a pro skipper. If you want to crew on somebody else’s boat, a two-week training voyage can cost $4,000 to $6,500.

The weather: No matter the route, the weather tells us when to go—or not. Rallies provide a pre-departure weather briefing and daily updates at sea. You can retain your own weather-routing service, or you can do your own forecasts underway with an online service such as predictwind.com or windy.com.

Resources: In addition to the resources listed throughout this article, I find it helpful to have copies on hand of Street’s Cruising Guide to the Eastern Caribbean and Transatlantic Crossing Guide by Donald M. Street Jr., World Cruising Handbook by Jimmy Cornell, Sailing a Serious Ocean by John Kretschmer, Offshore Sailing: 200 Essential Passagemaking Tips by William Seifert, Handbook of Offshore Cruising: The Dream and Reality of Modern Ocean Sailing by Jim Howard, and Ocean Sailing: The Offshore Cruising Experience With ­Real-Life Practical Advice by Paul Heiney. 

David H. Lyman is an award-winning writer and photographer based in Maine.

The post Three Ways South to the Caribbean appeared first on Cruising World.

I came to Lahaina from the south. After 13 days on an unleashed reach out of French Polynesia, I clung to the mast top, my legs wrapped in a death grip. We swung west into Alenuihaha Channel, known to Hawaiians as the river of laughing waters. The sun blazed and the trades howled as 20-foot rollers raced up our stern and frothed over the rails. Flying our heaviest chute was risky, as the channel boiled with towering whitecaps, but the Beach Boys blared from the deck speakers, and Maui loomed ahead in all its verdant glory. Cobalt-blue waves cascaded on the approaching lava rocks of Kaupo. Hana stood lush to the east, with the Big Island’s Mauna Loa and Mauna Kea silhouetted to the south.

I hadn’t been back to America in years, and I now charged full-tilt—unvanquished from the south seas under a swollen spinnaker, drunk on Brian Wilson.

It was gnarly up the mast. The horizon was a sweep of white water wrapped along the Maui shore, with roller after roller that threatened to bury us in the troughs. We broached, like a dog shaking a rat on a rope, and I slammed hard onto the deck with the bosun’s chair tangled around my legs. Our keel broke the surface as we buried the spreaders and spun out of control. All of us hung white-knuckled until the boat shuddered violently and tried to stand. We were a seasoned crew, baked brown and stringy by the sun. We hadn’t dropped the chute in 2,000 miles since leaving Tahiti. The closer Maui inched, the more we felt invincible. Landfall does that. After days at sea, every south sea island is an intoxicating rebirth of the senses, a virginal stirring of the heart. Lahaina was all of that. We had the boat tidied by the time we slipped past Kaho’olawe, into the lee of west Maui and the tranquil, humpback-strewn waters between Lahaina and Lanai.

Among cruisers around beach fires back in the South Pacific, Lahaina’s reputation was as a dusty, one-horse whaling town. I was on the beach in Huahine, set to hitch a berth to New Zealand, when “Hurricane Annie” Musselman, a striking female sailor fresh ashore after a 20-day sail from Maui, convinced me of the fun awaiting me in Hawaii, where I could then catch a boat to New Zealand next season.

In Hawaii, an endless arrival of passagemakers and wannabe sailors from the mainland made Lahaina their first stop. Those flying over never felt the same passion for the place; landfall was the only way to fathom the prize of Lahaina. From the sailor’s eye after days on the open ocean, Lahaina offered seduction like no other, bathed in the late-afternoon sunset sweetened by the fragrance of tuberose and mango that wafted miles offshore.

It wasn’t the thought of endless lilikoi cocktails, or the fantasy of tropically toned women exuberant with song and dance, their hair pinned with red hibiscus flowers and with plumeria leis around their necks. Beyond the fertile earth, fresh fruits, waterfalls, perfect surf, and harbor life of ocean sailors was the stunning Hawaiian backdrop and a celebratory welcome for sailors fresh from the sea, dues paid. Welcome to the land of earthly delights.

Lahaina’s harbor, first seen as mast tops peering over a small breakwall, was packed with working and provisioning yachts. At the entrance lay a weary 19th-century whaling ship, long in the rigging, and over its shoulder was an old missionary plantation home and museum adorned with whaling artifacts and reminders of the invasion of the Hawaiian Kingdom centuries ago.

The waterfront public library next door was the best place to watch the sunset through the palms, and next to that loomed the colonial, columned veranda of the Pioneer Inn, with its red roof, green sides, creaking wainscoting, whirring ceiling fans, open-air everything, and swinging saloon doors with a carved figurehead standing guard. The sound of a honky-tonk piano player pounding the ivories and wailing rousing tunes drifted from the saloon and across the anchorage, serenading us. Just beyond reach of the saloon was the canopy of an enormous banyan tree spreading a hundred yards in every direction. A missionary gift, it had been planted in 1873 by the widow of King Kamehameha. Lahaina, the capital of the Kingdom of Hawaii, which Kamehameha violently united, became the whaling capital of the world and commanded respect.

Even with its tin-pan serenades drifting across the water and its promises of revelry ashore, Lahaina was a sacred destination for those crossing the Pacific. Its backdrop was a riotous splash of color—a transformative sight after weeks at sea. Lush green cane fields rose up the slopes behind town, waving in the trade winds like a frozen sea. Red earthen foothills, ascending steep slopes to the majestic cloud-shrouded tops of the West Maui Mountains. Lahaina’s low-slung waterfront foreground bustled with green, shanty-style houses and humble shops all the way to the sugar cane mill, where every so often the sweet bouquet of molasses would blanket the town. Most harbor regulars nursed dreams of sailing to the South Pacific and were stopping just long enough to find a berth on a yacht heading south. Bikini-clad gals hawked sailing charters while gruff, unshaven sport-fishermen pitched billfish hunts. Sunset-cocktail-excursion captains, in bright-white uniforms with golden epaulets, recruited passengers. Sport divers in wetsuits hauling scuba tanks joined in the shouts amid the beer-drinking revelries of black coral hunters, stewed in their constant highs from too many daily 300-foot dives.  

Lording over it all, doling out privileges and access like a pirate king, was the leather-skinned, gray-bearded harbormaster. The rest of the town was second fiddle to the workings of that tiny harbor, the heartbeat of the town. Inebriated or not, the harbormaster could make or break sailing futures in this part of the Pacific. Flippant declarations boomed from the breakwall as he stalked the docks, banishing boats from the harbor, relegating them to endless hobbyhorsing at anchor, scheduling impossible departure times, and controlling the pace of work and supplies to replenish desperate sailors amid bribes, favors, and hard-luck tales.

A steady stream of entrepreneurs, street hustlers, harbor alcoholics, and starry-eyed youthful adventurers were always coming and going, convinced that they were at a pitstop en route to the South Pacific. Seemingly every waiter and waitress had dreams of being discovered, landing a berth on a boat heading south.

For many other locals, content with their hospitality and construction jobs, Lahaina was just home. Several hundred one-story houses of all shapes and tropical colors led from the water’s edge to the hillsides by the mill, sprawling neighborly toward the Kaanapali beaches to the north and the Olowalu beaches to the south.

Kaanapali, with its stretch of high-rise beachfront resorts, kept a good distance, about 4 miles from the hum of Lahaina, so their pampered guests could join the tourist hordes swarming town and then return to the civilized world of luxury Hawaiian resorts.

By contrast, many of Lahaina’s simply constructed neighborhood homes had basic tin roofs and green plywood sides, and were smart with a humble pride of ownership. Most houses had flourishing window boxes, and were peppered with hibiscus and plumeria hedges under the shade of towering mango and avocado trees with sweet gardenias, all thriving with minimal care. There was no need for heat or air conditioning, or even screens, in these homes. The streets were alive with locals and young folk making ends meet in town. Dogs barked, kids played, barbecues were everywhere, and bicycles were fine for getting around.

Kids wearing flip-flops and swimsuits skateboarded by the park or pedaled banana-seat bikes through town to the harbor break with surfboards under their arms. Pickups were the vehicle of choice, practical work vehicles suited to racing though cane fields. They’d cruise through town, tunes blasting with surfboards piled high, heading to the beach. Older locals surrounded by their broods of kids and grandkids hosted hula dances and strummed ukuleles beneath the banyan tree, or at the beach or grassy town parks, picnicking to beat the heat.

Lahaina was a tropical mecca of American pizzazz, where mainlanders swapped tales of the South Pacific. With the romance of the south seas under my belt, I was in no hurry to go back to sea, so I ran sailboat charters from here on a handful of yachts from 40 to 65 feet long that swept tourists off the beach for a heart-stopping sprint out to the Pailolo Channel wind line. We got a charge exciting the passengers, shifting without warning from a gentle, drink-sipping 7-knot drift to a rollicking, heeled-over, mai-tai-be-damned 15-knot dash into the teeth of the trades. If the passengers did not seem like they could handle the wind line’s excitement, we sailed calmly to Lanai’s Manele Bay, stopping halfway for a swim with the whales.

The real charter yachts were too big and too busy to handle the daily traffic in and out of Lahaina Harbor, so we sat on moorings off the resort hotels. There was Johnny Weismueller’s 60-foot 1929 schooner, Allure; Barry Hilton’s Alden 57, Teragram; the 54-foot aluminum ketch Minset; the Hermaphrodite schooner Rendezvous; and a handful of performance catamarans, which had the best layouts to accommodate hordes of tourist passengers, complete with midship bars, and could be rammed right onto the sand for loading and offloading. And the charter fleet wasn’t the only thing humming with intensity and tourists: Lahaina’s Front Street, the town’s waterfront artery, was the place to be. You could grab a drink at the Blue Max—a tiny, second-deck bar overlooking the seawall—and discover Elton John playing a surprise session on the piano. Jim Messina might drop in to perform at Kula’s Silversword Inn; Taj Mahal could be seen playing the congas to an empty beach at sunset; and Stephen Stills and David Crosby were regularly jamming aboard their boats at anchor. I recall Peter Fonda’s 73-foot sloop, Tatoosh, returning from the Marquesas, where I had recently shared trails with its crew while hiking the Nuku Hiva jungle. There were celebrities everywhere on Maui, a place where they could enjoy themselves without facing fandom.

One weekend, we filed aboard the square-rigged Rendezvous with friends and sailed to Oahu to hear the Eagles play Diamond Head crater. Days later, we rounded up our festival-weary crew for a quiet sail back to Maui. Getting around the islands was as easy as going down to the harbor and sticking out your thumb. One friend stood at the harbor entrance and hitched a ride on a sport-fishing boat heading to Oahu. He planted himself in the fighting chair and opened his paperback, ready for a nice read. Next thing he knew, the crew had hooked into something. They grabbed his book, strapped him in, and handed over a live rod. He spent the next four hours landing a 750-pound marlin for the first-ever fish thrill of his life.

Most of the Maui charter boats dragged lines just in case. They often landed ono, mahi, ahi and billfish. Once ashore, they would sprint to the best seafood restaurant in town and pocket a few hundred extra dollars for the crew. I recall a wedding sailing charter aboard Minset around Molokai’s Mokuhooniki Rock that double-hooked two big ono. After the wedding party fought and landed both fish, they returned to the dock bloodied, drunk and still smiling, with rave reviews.

The break at the harbor entrance was sweet enough to lure sunrise surfers from upcountry, a 30-minute drive from the volcanic slopes of Haleakala. As thick as tourists were in town, Lahaina’s waterfront shops had to cater to them. Along with its bounty of missionary folklore and whaling nostalgia, open-air bars, dive shops and salad bars, Lahaina sold trinkets, T-shirts, ice cream, Hawaiian-style jewelry, and the sort of faster food that tourists craving the hotel pool could quickly sample.

Around it all were the locals, living a life in the seams of tourist traffic, enjoying a shady beachfront tuft of palms and greenery, sitting with relatives on the sand, eating fish packets and coconut rice on the seawall. The proprietary goods that they depended on were relegated to tired one-story shopping centers on the periphery of town. The tourists came and went; it wasn’t difficult for residents to still feel a sense of steadfastness to Lahaina town. They tolerated the young people who moved in to take their hotel and tourism jobs. Compared with the relentless tide of visitors who abandoned their sensibilities when they became tourists, sailors often arrived with purpose and were commonly the most welcome of outsiders.

The famed Lahaina Yacht Club, host of the Victoria to Maui race and open to all visiting yachtsmen, was as unpretentious as there ever was a yacht club. It hosted none of the functions that typical yacht clubs host; it had no docks, no sweeping nautical lobby. Accessed through an insignificant Front Street doorway, the private club was disguised so well along retail row that visitors rarely found it on their first attempt. Inside, the dark, narrow hallway was decorated with photographs of classic sailboats finishing the Transpac and Victoria-Maui races, and framed letters from appreciative yachtsmen. A basic waterfront bar hung over the water with an intimate collection of tables. Dangling from the ceiling were burgees from visiting yachts from all around the world; upstairs, the loft had a few tables and backgammon boards. I participated in a couple of the Victoria-Maui races, as well as the dockside parties afterward. The bright-eyed patrons greeted us at all hours like heroes returning from the sea, offering flowered leis for each sailor, champagne, and lots of fresh fruit and pupus.

It’s an ecstatic moment for racing sailors, but cruising sailors wear their hearts on their sleeves and their first landfall is like a first kiss that can never be repeated. It’s a taste of wonder and redemption, almost salvation from any miscues of the passage, and a gratitude for an ocean’s drop of grace. In racing, the motivation is victory, the mission is speed, and glory the reward. While that’s a thrill worth seeking, in cruising, the promise of landfall is all heart.

The aching loss for this breathtaking Pacific landfall is that it will never be the same in Lahaina. The sailors will still come, but the landscape and the romantic legacy of a town that was an authentic kingdom’s home, a whaling mecca, a missionary post, and a working blend of tourism and local ohana is gone. What now remains of this legendary alluring paradise is but a barren gray stretch of ashen slabs and ghosts.

The town will be rebuilt and redefined by developers, legal setbacks and the buying power of realtors, but the soul of this Pacific pit stop and the prevailing Hawaiian spirit is at risk. The magic of this mythical landfall will never be quite the same.

Neil Rabinowitz is a longtime and frequent contributor to Cruising World as both a photographer and a writer. His work has appeared in Men’s Journal, Sports Illustrated, National Geographic, Outside, and The New York Times to name a few, and just about every marine publication. He has completed numerous ocean passages on both racing and cruising yachts and often finds inspiration recalling the romance of his first south seas landfall. He lives on a sunny farm on Bainbridge Island in the Pacific Northwest. 

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Set amid the azure waters of the Caribbean, the British Virgin Islands has long been a coveted destination for sun-seeking adventurers. With its vibrant coral reefs, quiet coves, and lively beach bars, the BVI is synonymous with relaxation and indulgence. 

The BVI is also renowned for its tourist attractions and well-­trodden paths, which is why, on a recent charter, our group of experienced charterers intentionally strayed from the familiar hotspots. In doing so, we found a side of the BVI that produced memories and stories anew. These newfound (to us) destinations offered a fresh glimpse into the singular charm of the BVI, which are just waiting to be discovered by intrepid souls who dare to look a little farther.

Sandy Spit

As the waves gently caressed the sides of our dinghy, I took a deep breath and gazed ahead at Sandy Spit, a tiny gem nestled in the heart of the British Virgin Islands. The sun painted a golden path on the water, as if guiding my wife and me toward a paradise we’d long dreamed of.

As the dinghy kissed the ­beachline, I leaped onto the ­pristine sands with anticipation and wonder, feeling the warmth radiating through my toes. Our friends had dropped us off for a few hours, promising to return later to whisk us away to the next destination on the itinerary. But for now, Sandy Spit was ours alone.

The island, barely more than a sandbar, stretched out in all directions, adorned with only a few swaying palm trees and a blanket of powdery white sand. The sand was cool and velvety, a luxurious carpet leading toward our own private sanctuary. We knew in a moment that this tiny island ­epitomized paradise in its purest form. It was a rare gift, a slice of heaven carved out just for us.

A simple isle merits simple pleasures, which, for us, included a charming picnic of tropical fruits, and the discovery of seashells and treasures that had washed up on the shore. Surrounded on all sides by majestic blue water and the beautifully jagged landscape of the BVI beyond it, it felt like we were all alone in the world’s most storied charter playground. Even today, when stress starts to get the better of me, I close my eyes and return to that perfect day on that tiny isle where time stood still.

Salt Island

A tiny droplet of moisture traced a path down my forehead while I leaned over the front of the RIB, maneuvering the painter to secure the dinghy to the mooring line near Black Rock Point on Salt Island. Submerged in the clear, shimmering water below were the remnants of the Rhone, a majestic steamship once belonging to the Royal Mail service. Its demise occurred during a hurricane back in 1867. 

With the dinghy secured and dive flag deployed, I glanced behind me for lurking jellyfish and then rolled backward off the dink, plunging into the bathlike water. An extraordinary world revealed itself: the vibrant dance of skittish reef fish, the kaleidoscope of corals in full bloom, and the whimsical sea turtle that was blissfully unaware of the concept of ­personal space. I swear that I almost heard the whispers of the 123 lost souls, as if they were keenly observing my every movement. It was ­haunting as each kick drove me deeper into the unknown, extending the boundaries of my comfort zone. 

While the Rhone is one of the most-sought-after diving destinations in the BVI, few charterers take the time to explore adjacent Salt Island, a place steeped in history and shrouded in mystery. Walking along the deserted shores, I felt a sense of awe as I discovered the remnants of salt pans that once served as the island’s lifeblood. I imagined the toil and perseverance of the salt miners of old. The weight of their stories added a layer of depth to the experience. 

History enthusiasts can learn a lot here about cultural heritage and the significance of salt production in shaping the region’s economy—not to mention escape from the crowds while reveling in the island’s seldom-touched beauty.

Fallen Jerusalem

As tourists flocked to the iconic giant boulders of the Baths on Virgin Gorda, I sought a quieter and more intimate experience. I’d heard whispers of a secluded cove nearby named Fallen Jerusalem, so we sailed across the channel toward it, accompanied by playful dolphins that danced in our wake. 

Approaching the shore, we were greeted not by other charterers, but instead by towering cliffs draped with vibrant greenery, framing a pristine beach. A leisurely stroll along the shoreline revealed hidden tide pools teeming with vibrant marine life. These natural pools, like tiny windows into an underwater world, offered a unique opportunity to observe colorful fish and delicate coral formations up close. 

Fallen Jerusalem has captivating underwater caves and grottoes that ­snorkelers and divers can explore under a cloak of solitude. The surrounding waters are protected as a marine sanctuary, ensuring the preservation of the island’s underwater ecosystem and contributing to ­sustainable tourism practices. 

Spring Bay

Spring Bay is a frequently overlooked beachcomber’s paradise. Sprinkled (although less liberally) with the same awe-inspiring granite boulders as its famous neighbor, the Baths, Spring Bay’s sprawling beachline offers a sense of peaceful grandeur. The soft white sands, calm waters, and swaying palm trees make it an idyllic spot to unwind with a Painkiller cocktail in hand and without the distractions of crowds.  

We had heard rumors of the great beaches surrounding the Baths, but nothing could have prepared us for the expanse of powdery white sand that ­greeted us like a welcoming carpet, nestled perfectly in the island’s lee. Turquoise waters lapped gently against the shore, inviting us to dip our toes and settle into a lovely, lazy beach day. We set up camp beneath the shade of a towering palm tree and spread out our beach towels to enjoy a picnic lunch and some tasty libations from our own galley, which was on the hook about a hundred feet off the shoreline. We reveled in the warm embrace of the ocean, our laughter echoing off the rocks as we played in the cove like carefree children. Donning snorkeling gear, we were instantly transported to a world teeming with schools of fish darting around us, and delicate coral formations posing as intricate sculptures. 

After a few carefree hours, Spring Bay became more than a beach to us; it was a cherished memory. Later, basking in the warm afterglow of a day well spent, we recalled how boat after boat had cruised right on by this picture-perfect setting on final approach to the Baths, without so much as a glance. Ah, their loss. 

Anegada’s North Shore

To go or not to go? That is always the question about Anegada, especially if it involves motorsailing for several hours head-to-wind. Weather permitting, I say go, but not just for the food. It’s easy to become captivated by the island’s succulent lobster and breathtaking beaches, however, the hidden gems along the north shore truly make this stopover a must-do. 

First off, because the lengthy offshore trek to get there isn’t for everyone, Anegada allows you to escape the crowds. The beaches are the epitome of ­untouched beauty, with fine white sands that stretch for miles and gin-clear waters that seem to merge with the sky. But the crown jewels of the north shore are its thriving coral reefs. Snorkeling or diving in these waters offers a glimpse into an underwater wonderland where colorful fish dance amid massive, shallow coral formations. The ­abundance and ­diversity of marine life will leave you in awe, making for an ­unforgettable adventure.

Anegada is a relatively small island, so getting around is straightforward. To reach the north shore, rent a moped or an RV. Driving along the quiet roads allows you to soak it all in at your own pace, and you’ll have the freedom to explore the hidden coves and secluded beaches that dot the coastline. Make sure to visit Cow Wreck Beach and Loblolly Bay, two secluded stretches of pristine shoreline with world-class reefs for snorkeling. As the sun begins to set, make your way to Flamingo Pond Lookout to witness majestic flamingos in their natural habitat. 

After a day on Anegada, you’ll probably have worked up a healthy appetite for the legendary lobster. To the victors belong the spoils. 

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