“Aww, c’mon man, don’t let us be that boat!”

I shouted at myself as I cranked the wheel and goosed the throttles, sending the Lagoon 42 Sjevernjaca into a wide, lumbering 360-degree turn. We had to get out of the path of a powered-up race boat that was bearing down on us. 

Standing next to me at the raised helm station was my old sailing mate Dave Robinson. “Oh, that one’s going to be trouble too,” he said three-quarters of the way around the circle, pointing at a sailboat that tacked close to shore and was now headed our way.

I spun the wheel hard again and searched for an open path through the oncoming traffic. The seas were lumpy off the rocky entrance of Antigua’s English Harbour.

It was Day Two of Antigua Sailing Week, which we’d come to watch, not participate in—though now, apparently, we were in the thick of it. Dream Yacht Charters was a sponsor of the event, and when they suggested that I take in a bit of the action and then sail off to see the rest of the island, well, how could I say no? 

We had started two days earlier at the charter base just up the coast in Jolly Harbour. On the last Saturday in April, after provisioning at Epicurean Fine Foods & Pharmacy and then waiting for a leaking faucet to be replaced, we got a late start. Our destination was Falmouth Harbour, home to race headquarters and the first stop on a counterclockwise, weeklong circumnavigation of the island. At the chart briefing that morning, besides a rundown of must-see bays and coves (and a review of the island’s many reefs to avoid), we were told two things: Be on a mooring or anchored an hour ­before sunset, and keep clear of the 85-boat Sailing Week fleet.

With the first advisory top of mind, we motored out the channel in midafternoon, hung a left in open water, and made a beeline for Goats Head Channel, staying inside the reef on the island’s southwestern side. To my surprise—given that this year’s Sailing Week was the first at Antigua after a two-year pandemic hiatus—Falmouth Harbour was not all that crowded. We had no problem picking up one of the Antigua Yacht Club’s guest moorings, relatively close to its dinghy dock. It turns out the bulk of the racers preferred to crowd into adjacent English Harbour, home to Nelson’s Dockyard and a number of marine facilities.

Ashore, we learned that the opening-­night party, to which we’d been invited, had been canceled because of pending weather. The bar was open, though, and the drinks were flowing. Decked out in team colors, sailors clinked bottles and glasses as regattas past were toasted. Outside, several race boats were tied along the docks, their crews offloading gear in preparation for Sunday’s opening race. And on a nearby waterfront stage, the Original Steel Orchestra entertained one and all with a lively assortment of Caribbean tunes.

For dinner, we took a security guard’s advice and walked a short way to the Life on the Corner Bar & Grill, which served up a spicy chicken curry that demanded to be washed down with cold Caribes, followed by a sweet rum punch. The street outside was busy and loud. Back on the boat, we sat forward on the tramp and enjoyed a ringside seat.

Sailing Week, according to its president, Alison Sly-Adams, marks the end of the Caribbean’s regatta season. It started in 1968 as a reason for yachts and crews to stay just a bit longer before heading north, out of hurricane danger or back to Europe. This year’s event was the 53rd regatta, offering racing action to a wide array of sailors. Boats ranged from thoroughbreds such as the Volvo 65 Ambersail 2 and the Volvo 70 Ocean Breeze to mom-and-pop cruisers to a fleet of 29 chartered bareboats. There were 15 classes in all, assigned to two starting areas just to the east and west of the entrance to Falmouth Harbour. 

We joined the eastbound parade of boats Sunday morning to watch a few of the big-boat starts. The action began at 10, with classes taking off at ­five-minute intervals. By the second tack, the front-runners in each heat were lost in the Caribbean haze, so eventually we headed over to the B Fleet’s windward mark and puttered around, watching the spinnaker-­optional cruising and bareboat classes at work. With a broach here, an hourglass chute there and a few collisions with the inflatable buoy, it was all entertaining enough.

The trade winds were forecast to be sporty throughout the week, and they were. After a long morning of bouncing about in the resulting swell, our crew embraced the idea of returning to the mooring to take in a little more of what Falmouth had to offer. We had an invitation to a rum party being put on by Locman, the Italian watchmaker, and then grabbed a $12 cab to Shirley Heights a couple of hours before sunset for the infamous Sunday night jump-up party.

Even on a quite-hazy evening, the view of English and Falmouth harbors from atop Shirley Heights was breathtaking. The place was packed by the time we arrived, and a long line pointed the way to the barbecue pits, where cooks prepared chicken and ribs over wood and charcoal fires. Nearby, craftsmen laid out tables filled with wares. I watched a basket weaver make youngsters happy by fashioning fanciful hats for them out of palm fronds. The bar was busy too, serving libations to a mellow crowd of sailors content to sway to the Caribbean rhythms of the Halcyon Steel Orchestra. 

We watched twilight turn to dark and then headed back down to town, and from there to the boat for a hot dog feast cooked on a charcoal-fueled grill of our own. With the jump-up and Sailing Week visits crossed off the to-do list, we were ready to go exploring.

On the chart, it looked to be about 12 nautical miles to Nonsuch Bay, the first protected must-see anchorage on Antigua’s east coast that was not off-limits to Dream charterers. With just that seemingly short distance to go, we were in no hurry to get started. At the mooring, the breeze felt lighter than it had the day before, but as soon as we were outside and turned east to clear the tip of the island and proceed north, the trades were full-on, gusty and squarely in the no-sail zone of a big cruising cat. Three things became immediately apparent. First, we were in for a long, slow motorboat ride, pounding into ocean swells that made it hard to get boatspeed up to even 5 knots. Second, the A Fleet race committee had designed the day’s distance course to take several classes along the very same coast we needed to traverse. And third, we should have left a whole lot earlier in order to be out of their way.

For the better part of two hours, we played dodge ’em with incoming race boats. In all, it was a wet three-plus-hour slog up what was a textbook lee shore, with water pouring over the cabin top each time a bow buried itself in a wave or a squall rolled through. But still, it was a thrill to see the wildness of the sea, feel the power of the breeze, and take in the lush green hills and rocky outcrops that marked this part of Antigua. I’d do it again in a heartbeat, though perhaps not in the midst of a regatta.

Soon enough, we spotted a white structure on a headland that the cruising guide said looked like a lighthouse. Just past it lay the pass into Nonsuch Bay—a slice of deep water through outcroppings of rock and coral jutting out between the mainland and Green Island. As we turned and ran west, surfing down the ­wind-driven swells, the early-afternoon sun was high overhead, making it easy to spot the shallow spots. Closer to shore, the waves laid down, and once inside, though a gusty wind still blew, the water was calm. Relief!

Nonsuch Bay is a truly lovely place—my favorite spot of the week, I think. Inside, to the east and south, the hills are tall, with a few homes and resorts tumbling down to the water. Just past the entrance, there’s Middle Reef to skirt, with good water to either side. To the right, there were a couple of boats anchored off the northeast end of Green Island, and farther along, a handful more tucked in behind the reef.

We broke left and motored deep into the bay to what, on the chart, appeared to be a well-protected spot surrounded by mangroves in Ayres Creek. We dropped anchor in about 12 feet of water just off a resort dock, and then watched a cloud of mud billow up as we backed down and plowed the hook along the bottom.

Plan B? Head back to Green Island and anchor in sand. Besides way better holding, we found great entertainment, thanks to 40knots—a local watersports school that offers kite-, wing- and paddleboard lessons off the beach and from a sailboat anchored by the reef. We witnessed a variety of skills. There were soaring leaps and landings, as well as the occasional chase-boat rescue of a newbie blown astray. As for our crew, we grabbed masks and snorkels to sit on the beach at Green Island. Underwater, there wasn’t much to see, save for one enormous hermit crab. It was a good swim, though, on a hot afternoon.

Sunset that night was the best. The sun dipped below the hills to the south, and the water inside the reef was calm, the breeze steady. If cruising, this bay would be a place you might stay for days or weeks. Unfortunately, we were on rented time and had places to go.

Tuesday got off to another wet and bumpy start. We followed our track back out the pass, planning to motor upwind until we were clear of Green Island and could set sail for Horse Shoe Reef Channel and the entrance to Parham Sound at the north end of the island.

As we retraced our steps, the waves built as quickly as they’d subsided the day before. One roller caught me off guard, and rather than bearing off to take it on the forward quarter, Sjevernjaca plowed square in, burying both bows with a shudder. Stepping below, one of our crew discovered water in the hallway outside his forward cabin; inside it was more like an aquarium. A hull hatch had been left open. As if to prove a point about the power of hydrodynamics, the sea had sent remarkable amounts of water pouring in, soaking everything in its path.

At last in deeper water, the seas mellowed. We hauled up the main, cracked off, and rolled out the self-tending jib. Sailing, at last! It was a good 5-mile reach that began with breeze on the beam and ended up with us nearly on a run. 

The coast along this part of the island is low-lying, making it tricky to pick out landmarks. We searched for Prickly Pear—a sandy islet just offshore that serves as a range mark through Horse Shoe Reef Channel. Once we spotted it and made our turn, even with the aid of the chart plotter, the shallows to either side of the channel were hard to spot until we were nearly on top of them, but we made it through and followed the charted route south through reefs to the sandy beach at undeveloped Maiden Island. It turned out to be a good spot to swim and kick back. With the VC Bird International Airport across the way and boat traffic passing by, there was plenty to watch. Toward sunset, two cruising sailboats pulled in, but otherwise we had the place to ourselves.

In the morning, we set sail and picked our way back along the shore, passing inside Prickly Pear, bound for Boon Channel. The route kept us well off the reefs to the north. In daylight, with a chart plotter, this was an easy passage, but looking at the Imray Iolaire chart on board, I once again had a great appreciation for Don Street plying and charting these waters with a compass and lead line as he mapped and wrote his cruising guides aboard the engineless yawl Iolaire.

Our journey that day—and for the rest of the trip, for that matter—delivered a nice, but brief, sail. The distance from Maiden to Dickenson Bay is just 7.5 miles, and we flew along with the still-gusty trade winds behind us. Dickenson is home to Sandals and a couple of other all-inclusive resorts that dominate the long, crescent beach, but we found an open stretch at the south end and anchored there late morning in about 9 feet of water, near a thatched-roof raft known as the Kon Tiki Bar. 

After lunch and a swim, three of us were eager to go ashore and stretch our legs. With no good place to land or leave a dinghy, one of our crew dropped us at the beach, where we followed a rutted dirt road to a paved one. Resorts lined one side of the street; on the other, we strolled past a large pond and an abandoned miniature golf course, complete with a faded cruising catamaran that doubled as a hazard. A local pointed us in the direction of a small convenience store, saving us a long walk or cab ride to a market to replenish our dwindling stock of beer and chips. 

Later that afternoon, we visited the tiki bar—our first watering hole since Falmouth that wasn’t all-inclusive and that was open to non-guests. It was a lively place, and “Johnny from Denmark” ruled the bar. He was quick to serve us a cold Caribe when we stepped aboard from the inflatable.

Johnny had a tale to tell. He’d come to the island for a two-week visit 22 years earlier and, well, fell in love with the place. He managed a restaurant on the beach for several years but lost it when the owner died and it changed hands. Four years ago, he made good on a dream to build and open the Kon Tiki Bar along with his better half. The pandemic was a setback, and, added to that, he and his partner split up, he said. Now he gets the raft for a week, then takes his liquor home, and she brings her own booze for the next. “That’s just the way it goes,” he said with a shrug. “I’m working one week, then I have a week’s vacation.”

An assistant sat off to the side of the bar and manned a runabout to ferry visitors back and forth to shore if they didn’t want to make the short swim. As the day went on, the number of visitors grew and the music got louder. By the time we left, it was packed with a raucous crowd awaiting sunset.

Thursday was our last full day aboard Sjevernjaca, and as the crow flies, we didn’t have far to go to skirt the entrance to St. John’s Harbour and arrive at our next destination, Deep Bay. The breeze was still honking from the northeast and we were in no hurry, so we hoisted sail and struck out on a long reach out to sea and back, getting in a couple of hours of good sailing before dropping the hook.

Deep Bay was yet another lovely destination. As we motored in, we had no trouble spotting and avoiding the wreck of the Andes, a barque that had caught fire and sunk while carrying pitch to Chile in the early 1900s. Inside, we anchored in about 9 feet of water. 

The Royalton Antigua resort takes up the southern end of the beach, and a few small shops dot the shore, but most of the strand is backed by lush green shrubs that hide a salt pond behind. Ashore, we scrambled up the steep path to Fort Barrington, built by the British in 1779 on the headland overlooking the approach to St. John’s. The view was spectacular. We could just spy Montserrat through the afternoon haze, and we got a panoramic view of Antigua’s mountainous interior. 

Friday, we managed to create another extended sail for ourselves by reaching out past Sandy Island and its off-lying reef, and circling back to visit pretty Hermitage Bay and Five Islands Harbour, where the Shekerley Mountains tower over the anchorages. We stopped for lunch and a swim, and lingered as long as we could before motoring out and around the point, back to Jolly Harbour and the charter base. It had been a fine week with plenty of breeze for sailing, a happy crew, and sights to see. 

Saturday morning, as we cleaned the boat and packed, I spotted the crew from Talitha on the dock. I’d met them at the start of the week, when they were getting their rented Beneteau Oceanis 41.1 prepped for action. Skipper Jeff Dickinson along with the rest of the crew of eight all hailed from Aspen, Colorado, and are members of the Aspen Yacht Club. It was his third Caribbean regatta, he’d said. And of course, they expected to win their bareboat cruising class. 

“I love Antigua,” he told me. The pace of the regatta is just right: two to three hours of racing, then a party, plus a lay day for scuba diving.

So how did they fare? 

Well, they had fun. Dickinson was back at a rented condo where half of the crew had stayed at night. But his mates who returned the boat reported that Talitha was first over the line in three races—a victory of sorts—though they ended fifth overall on corrected time. One thing they were certain about: They’re coming back to race again. “Absolutely.”

Mark Pillsbury is a CW editor-at-large.

Charter Racing

Antigua Sailing Week is one of several Caribbean regattas that include a charter-­boat division. For this particular week of racing, Aspen, Colorado, skipper Jeff Dickinson said that charterers can’t request a particular boat and can’t campaign the same boat two years in a row. § Erin Minner, Dream Yacht Charter’s sales manager for the Americas, says that racers have a few other requirements to consider. The minimum charter time is 10 days. There is a race-pack charge that includes a more detailed boat briefing and a check to ensure that sails are in good shape. The base registers the boat with race officials. There is a regatta surcharge of approximately $2,000, depending on the boat and event, and the security deposit is doubled. Dream Yacht Charter lets its boats participate in Antigua Sailing Week, the Caribbean 600 and the BVI Spring Regatta. § If you’re planning to escape winter and go racing, check with the regatta and local charter bases for yacht availability.

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As I made my way toward the stage, stepping carefully through the children seated cross-legged on the floor, a familiar tune rang out in the tropical night. A tall guitarist and his sister led the crowd in a cruiser’s version of perennial favorite “The Lion Sleeps Tonight.”  

Daily plotting the fleet positions, we read the new forecast. 

Carefully checking all the veg to see what did not last. 

Joining in were faces now familiar to me: a British woman with a ukulele, a father-­daughter duo on violins, a young American man on a tiny electric travel guitar. Less than a week earlier, these sailors had been strangers. Now, on the final night of the weeklong festivities and ARC Plus welcome events, I sang along with the families and crews who had made the journey across the Atlantic. 

The World Cruising Club’s Atlantic Rally for Cruisers began in 1986 as a way for sailors, especially amateurs, to participate in a race across the Atlantic. The ARC emphasizes camaraderie and safety within the fleet for the 3,000-nautical-mile passage from the Canary Islands to St. Lucia. The ARC Plus route was added in 2013 to meet growing demand, as well as to give participants the option of breaking the journey into two legs. The ARC Plus route ­traditionally takes the fleet from the Canary Islands to Cape Verde, followed by the 2,000-nautical-mile passage to St. Lucia. This year, the ARC Plus saw 70 boats with crew from 26 countries depart Gran Canaria and sail south “until the butter melts.” After a short stopover in Cape Verde, the fleet set their sights on Grenada for the first time. Moving the ARC Plus fleet to Port Louis Marina in St. George’s eliminated the pressure on the ARC Plus participants to move on from St. Lucia to make space for the direct ARC arrivals.

A few days before the first boat arrived in St. George’s, I reached out to Sally Eardle, a family friend and the owner and editor of the Caribbean Compass, a local sailing newspaper. Sally is a veteran of the ARC arrivals, and I asked her if she thought I’d be able to jump into the festivities. She assured me that the fleet is known for an infectious positivity. “People are usually happy to speak about their experience.” I learned quickly that she was right.

During my first morning on the docks, I met Dale and Megan Simonson, on Helios, an American father-daughter duo from Illinois who were new to sailing and crossed the Atlantic on their Lagoon 52 with three other crew. Megan, 18, is a recent high school graduate on a gap year, and was the catalyst for this adventure. “We wouldn’t be here if it weren’t for her,” Dale told me. “She gave me the courage to retire and buy the boat.”

Dale and Megan introduced me to Traci and Andrew Roantree on the British-flagged Beneteau Oceanis 45 Walkabout, but our conversation was cut short. “I need to get to ukulele practice,” Andrew said. I was intrigued. He told me that a member of the fleet had written a song about the ARC Plus, and a few sailors had bought ukuleles in Cape Verde with the intention of learning the music during the passage, but of course most of them didn’t; they were ­headed for a last-minute practice.

I continued on my way, only to come across another ukulele student. “My husband is the mastermind behind the song,” Lori Green told me as she pointed to a tall, slender man with a guitar case on his back. “It’s just a fun little thing I do for the rallies back home,” Barney Green said. The Greens have been living aboard their Bavaria 51, Favorita of Hamble, since June 2020. They had originally planned to do the ARC Plus in 2020, but like so many others, decided to postpone their cruise due to COVID. “Anyway, we’re here now,” Lori said with gratitude and relief. Barney told me that he began writing songs when he was the commodore at the Newbury Yacht Club, just outside London. The yacht club is “famous for being possibly the farthest yacht club from the sea,” he said.

I hung around to see who else was part of this merry little band of sailors, and ran into Paul Youngblood, whom I had met the previous day aboard his uncle’s Ted Hood 52, High Cotton. Paul, a 24-year-old from Minneapolis, is first mate on board and is on the last leg of an Atlantic circumnavigation with his uncle, John. Having crossed from Newport, Rhode Island, to the Azores in June 2021, they plan to take their time cruising the Caribbean, with Paul staying on board while John flies in and out from his work in financial services in New York. They did the crossing with two other crew on board, but it wasn’t without its challenges—namely, the misprovisioning of coffee and the necessary rationing that ensued. “Two and a half cups of caffeinated and one and a half of decaf per person, per day,” Paul had written on their blog shortly after departing Cape Verde. This misfortune was compounded by the fact that their autopilot stopped functioning during the first leg, forcing the crew to hand-steer for the duration of the Atlantic crossing, though they didn’t seem phased. “I’d say we’re all much better at the helm now than we were before,” John said with a laugh. 

The High Cotton crew’s modest versatility was a common trait among the ARC Plus participants and planning committee. I got the chance to talk with Trish Jenkins, one of World Cruising Club’s famous Yellow Shirt team members. The Yellow Shirts are the boots on the ground who make sure events go off without a hitch and provide unwavering support to the participants. “We really didn’t know what events we’d be able to do this year, but we’ve worked closely with all the officials here [in Grenada], and it’s just fantastic to still be doing the ARC Plus,” Trish told me.  

Among the most flexible and resilient participants are perhaps those on the family sailboats, many with young children aboard. Christian and Julie Pukelsheim on the Contest 42 Lady Blue had been planning for five years to cross the Atlantic with their three kids, now ages 11, 8 and 4. Unfortunately, when sudden and severe seasickness struck all but one of the children during their four-month voyage from Northern Spain, they were forced to rethink their plans. In the end, Julie and the kids flew across while Christian, who dreamed of having a family Christmas under a coconut tree in the Caribbean, found some last-minute crew to sail with him. As for their plans now? “We’ve been planning this for five years, and the plan ends today,” Christian said of his German family. “It’s a totally new feeling to not have a plan.”

I got a similar response from Australians Tillman and Verena Coxhead on board their Dick Zaal Skimmer 39, Big Bubble. “We made plans to come here, but we never thought we’d actually make it,” they told me. Their youngest of two children, Caruso, celebrated his 2nd birthday in the middle of the Atlantic and was one of the youngest in the fleet this year. When I asked them if they had any concerns about crossing the Atlantic with such young children, they assured me that they didn’t. “Any family boat who thinks about doing something like this, I would encourage them to; it’s a once-in-a-lifetime experience,” Verena said.

The same sentiment was echoed by most of the ARC Plus sailors. Maybe it was the fact that so many had postponed the adventure for a year due to COVID, or the uncertainty of last-minute changes and unexpected challenges, but everyone seemed incredibly grateful and relieved to finally be in Grenada. After the final evening of award presentations and celebrations, as Sally and I made our way back to the marina, the last verse of the ARC’s unofficial song played in my head:

Finally landing in Grenada, we smell, we’re tired, and it hurts. 

Hoping rum punch will make things better, we search for yellow shirts. 

I asked Sally how this year’s ARC Plus event compared with ones in the past. “You know,” she told me, “every ARC is different, but I think this one really had something special.” 

I couldn’t agree more.

Lexi Fisher is a Grenadian/Canadian writer, freediver, and co-author of The Cruising Guides to the Windward and Leeward Islands.

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My friend Larry Tyler and I have known each other and sailed the Caribbean together for years. Larry has been chartering The Dove, his 54-foot Bill Crealock-designed yacht, in the islands for 30 seasons. So he was the natural person to ask perhaps a not-so-simple question: What are your favorite places to drop the hook in the Caribbean?

“What criteria do we use?” he wondered. “What defines a desirable anchorage?”

“I want clear water for swimming, and to see the sunset each evening,” I said.

He took that simple yardstick and ran with it. “It must be unspoiled, a near-empty place,” he added. “With good holding ground and access ashore. My charter guests want it calm, with no swell. A nice local or French restaurant ashore is always a must. Certainly, no bugs and good snorkeling.”

“A small village with a farmers market, and trails for hiking ,” I countered. With these conditions in mind, we set about drawing up our lists. Mine included three coves in the British Virgin Islands. Larry began in Anguilla. We both ended up in Grenada, at the southern end of the chain.

“Anse Colombier on St. Barts is my ideal,” Larry said. “No roads, no houses, no bars, no restaurants, a great beach and hiking trails. And the town Gustavia, with a patisserie, is a 2-mile dinghy ride away.”

“Five Island Bay and English Harbor on Antigua are my favorites,” I replied. Then again, there’s Deshaies and Les Saints on Guadeloupe, and Saint-Pierre and Sainte-Anne on Martinique. Choices, choices! We both agreed that the anchorage beneath the Pitons on St. Lucia is memorable. I liked Bequia, though Larry insisted it’s getting too popular. He preferred Cumberland Bay on St. Vincent and Chatham Bay on Union Island (where he and his mate, Justina, spent much of last year during lockdown).

I must say, I could spend a month in any one of these anchorages. But when push came to shove, Larry and I jotted down our notes on eight great, specific Caribbean anchorages. You can’t go wrong with any of them.

Five Island Bay, Antigua

Larry and I sailed The Dove into Five Island Bay late one night in November 2019—the conclusion to a three-week delivery from Maine. When I awoke the next morning, the sun was peeking over a series of small hills that encircles this large, open bay. We were the only boat anchored in paradise.

If you get in close enough to the exclusive Hermitage Resort, you might pick up its free Wi-Fi. Evenings, the jazz singer at the resort will lull you to sleep, then it goes quiet by 10 p.m. Half a dozen coves and beaches encircle the bay, but few boats anchor there. I’ve never seen more than five at a given time.

There, then, is solitude. But a mere 12-minute dinghy ride brings you into Jolly Harbor, an extensive marine complex that’s more Fort Lauderdale than Caribbean. There’s a marina there, a boatyard, fuel dock, restaurants, and the best supermarket on the island. There are rental cars, a marine chandlery and a pharmacy, and you can clear in and out there. Pretty much all the bases are covered.

English Harbour, Antigua

There’s only so much solitude a sailor can take before needing to get back to civilization. An hour away from Five Islands is one of sailing’s great meccas: Falmouth and English harbours. That fall, before the pandemic hit, we anchored The Dove off Pigeon Beach. Falmouth is a large harbor with lots of room. Most everything you need can be found in the village of English Harbour: fuel and water, a chandlery, a sailmaker, a repair yard. A lone farmer has his stand by the dinghy dock; the laundry is directly across the street. The Seabreeze Cafe, next to the Yacht Club, has Wi-Fi, and restaurants abound in this village devoted to sailing.

Huge mega-yachts, liveaboard cruising boats, dinghies, bareboat charter yachts, paddleboarders, and everything else that floats come and go all day long. There’s always something going on there: the Charter Yacht Show, the Classic Yacht Regatta, Antigua Sailing Week, a lone rower paddling in having just crossed the Atlantic. As I said: whatever floats.

It’s a short walk to Nelson’s Dockyard and a step back into the 1700s. This restored British naval base has a museum, bakery, rum locker and the famous Admiral’s Inn. Yachts are docked stern to, with more riding at anchor out in Freeman Bay. Heading up to Shirley’s Heights for the sunset ritual—a rum punch, a steel band and a view—is well worth the 30-minute hike.

Deshaies, Guadeloupe

It’s 48 nautical miles of open-ocean sailing from Antigua across the waters to the lee of Guadeloupe and Deshaies, a small harbor tucked in between two tall cliffs. I could spend weeks there—and in fact, I have. It’s there you clear into France. The customs and immigration “office” is a computer inside La Pelican Boutique. This small, one-street village is not on the cruise-ship ports or the tourists’ bus excursions. It’s a residential town with three small groceries stores and the best tomatoes and pineapples I’ve tasted. The patisserie opposite the dingy dock has fresh croissants and baguettes every morning (though your coffee comes out of a coin-operated machine). There are a few boutiques, an ATM, three dive operators, and rental cars, but no yacht services or supplies. Wi-Fi is available at Le Madras, a thatched-roof cafe right on the beach.

Just around the corner is a mile-long sandy beach. Take the dinghy around and anchor outside the break, or walk over on marked trails, around or up over the cliff. An hour south is the Cousteau Underwater Park, ideal for snorkeling and scuba diving. A hiking trail follows a stream that runs down from the mountains, tumbling over boulders and splashing into pools just right for a swim. A mile south of the village is an extensive botanical garden park. My family and I spent half a day there last year.

The holding ground in the harbor at Deshaies is not great, so make sure your anchor is well-set. The wind can occasionally come blasting through the mountain valleys. An East Coast storm will send swells into Deshaies, and conditions will become uncomfortable and dangerous. I recently had to up-anchor and escape those swells. It must be said: Paradise often comes with her blemishes.

South of Guadeloupe: Les Saintes

Les Saintes is a cluster of small islands with a single village, 6 miles south of Guadeloupe. Last year, we found a vacant anchorage between Tête Rouge and Pain de Sucre, in 30 feet of clear water. There are other anchorages among these isles, but the closer into the village of Bourg des Saintes, the more crowded it becomes. Our solitude meant a 10-minute dinghy ride into town—nothing too onerous. Ashore, the village hadn’t changed since I was there 20 years prior.

Here’s Larry’s take: “Mornings, we sit at a bakery on the beach with coffee and croissants, watching the village wake up. On my last visit, French schoolchildren, in uniforms, scampered past as shopkeepers swept the pavement in front of their stores, their colorful fabrics and local artworks spilling onto the sidewalks. We had the entire village to ourselves. Then, the first of a dozen ferry boats arrived at the town pier to disgorge hundreds of tourists from the mainland. The village was now abuzz, the single street packed. There are electric mopeds and bikes to rent, restaurants galore from which to choose, roads and paths to walk, beaches to visit. Fort Napoleon is a short hike away. But we had to mind those daredevil motocross kids as they zipped past!

“The crowd quickly thinned out, heading to the beaches to the south and east. This went on all morning, with the reverse in the afternoon. By tea time, we again had the place to ourselves.”

Sainte-Pierre, Martinique

It’s 70 nautical miles from Les Saintes down to Sainte-Pierre on Martinique. In other words, it’s an all-day sail with strong winds and higher seas between the islands. That said, you can stop midway for a few days of respite in the town of Portsmouth, on Dominica.

On our last visit to Sainte-Pierre, we furled the sails and motored into the open roadstead along the port’s narrow beach. The only suitable anchorage is a narrow shelf that extends less than 500 feet from shore. Depths fall off quickly to 1,000 feet. If you can’t find a spot there, try a bit farther south, under the monument. Ashore, we found the restaurant we dined at 10 years ago, and the family tucked in for dinner. This town is extremely French and not touristy.

We rented a car and drove into the mountains to explore. We found a deserted and overgrown turnoff. The kids scampered down the slope to a cascading stream, and my wife, Julie, and I followed. There, we found small waterfalls, deep pools, smooth boulders, and spillways. We spent two hours slipping and sliding, swimming and floating in the cool pools. No one else was around.

Sainte-Pierre has a volcanic history, and there’s a museum to visit; the streets are lined with shops; and a large open market next to the dinghy dock has fresh local fruits and veggies. We filled our basket.

The cultural and economic differences between the French islands and their other Caribbean counterparts is striking. Guadeloupe and Martinique are large isles, with modern infrastructure, excellent highways and real cities. You could be on the Cote d’Azur. By contrast, while the former English colonies were left to fend for themselves, the country of France still holds claim to their islands, and spends lavishly on their tropical offspring…to the lament of the French people stuck back home.

Cumberland Bay, St. Vincent

Halfway down the west coast of St. Vincent is a small cove, Cumberland Bay. “This is my favorite anchorage,” said Larry’s mate, Justine. “It’s the real Caribbean. You can smell the jungle.”

“There are no tourists, no cruise ships, and room for just a few boats,” Larry seconded. “You have to tie off astern to a coconut tree on the beach. There are no streets, stores or shops, but there are a few barbecue shacks and restaurants on the beach. The fishermen there are very nice, and they are eager to meet you and talk—and of course, sell you fish! You can buy bananas, coconuts and vegetables from local farmers, and some of the men will organize a pig roast for you, right on the beach.”

Trails lead up into the mountains, the two main villages are a mile inland, and there’s a cricket pitch and sports field next door. Cricket is a major sport on many of the former English islands. Get to know your wickets.

Union Island, the Grenadines

Larry and Justine spent the first 10 months of the pandemic lockdown in the Grenadines, a string of small islands that includes Bequia, Mustique, Canouan, Mayreau, Union and the Tobago Cays. It was early April 2020 when they arrived at Union Island—the last yacht allowed into the territory.

“We anchored in Chatham Bay for months and months,” Larry told me. “It’s on the west side of Union, and like Cumberland, it’s the real Caribbean. There are no stores, just a dirt road leading over the hill to town. There are a few cottages for the fishermen who live there, and in good times, a couple of fish shacks serve up barbecued fish, chicken and lobster.”

“The fishermen came by every few days to sell us tuna, red snapper, lobsters,” Justine continued. “Ashore, there are hiking trails, the snorkeling is good, the water clear and clean. We got to know a fisherman and his wife who live on the beach. Larry helped them wire up a solar cell so they could charge their cellphone. There’s no electricity there! They invited us to spend Christmas with them, which we did.”

Bequia Island and Port Elizabeth

The Dove and two dozen other liveaboard yachts made Bequia home for much of the pandemic year. The harbor of Port Elizabeth and its small town had everything they needed: stores, an open fish and produce market, a chandlery, plus a few restaurants. They hiked the island, explored the beaches, snorkeled on the reefs, and worked on the boat. “The people were very happy to see us,” Justine said. “There was a potluck dinner somewhere each week for the cruising community.”

So there’s our shared list, which begs yet another question: Which is the best? It’s hard for me to choose a favorite Caribbean anchorage. I like them all, each for a different reason: shopping, snorkeling, hiking trails, waterfalls, and either the solitude or the shoreside community. It’s the “going back” to see each again that I like and appreciate. It’s like a good book, painting or photograph—you see so much more on each repeated visit. It might not be the island that has changed; maybe it’s me.

The important things are these: The deep blue Caribbean Sea spreads out before the bow; the mast and mainsail tower into a blue sky above; the green mountains of the next island rise up from the horizon. I’m back in the Caribbean, and that’s what matters.

David H. Lyman is a professional ­photographer, author and frequent contributor to CW. For more on Larry and Justine, and their travels on The Dove, visit their website, thedove88.com.

Planning Your Caribbean Escape

As vaccinations ramp up, more and more islands will hopefully be open to accepting guests, those arriving on planes and by yacht. Now is the time to begin researching your options, be it on your own boat, chartering a bareboat, or on a crewed charter yacht with a skipper and chef.

The eastern Caribbean has hundreds of islands in a 500-­nautical- mile arc, from the Virgin Islands down to Grenada. It is possible, even desirable, to explore the entire eastern Caribbean in a single winter season; but then again, you could stretch it into a lifetime. After all, you’ll want to linger in each anchorage for a week or two, even a month. A one-week charter might include an island or two, and you can do the BVI in two weeks. But the last thing you want to do down there is rush around. Here are what I consider eight groups of islands, each worth a full two weeks of exploration:

• The Virgin Islands: US and British
• Anguilla, St. Martin and St. Barts
• Antigua: with 365 beaches and two dozen anchorages
• The big French islands of Guadeloupe and Martinique
• Dominica: Ashore is worth a few days
• St. Lucia and St. Vincent
• The Grenadines: Bequia down to Union Island, including the Tobago Cays
• Grenada and Carriacou

You can go anytime, but the best weather is late fall and late winter into spring, when the weather is more settled and the bareboat charter rates come down. To begin planning, you’ll need Chris Doyle’s cruising guides to the Windward and Leeward islands (doyleguides.com). Doyle updates his guides yearly with detailed information on shoreside amenities, hikes, shops and services.

In the old days, before Doyle and the internet, there was ­legendary Caribbean cruiser Don Street’s Cruising Guide to the Lesser Antilles. You can still find used copies online. My copy is from 2000, but as Street would say, “The rocks are still in the same place.” Street’s guide is for serious sailors and navigators, and includes compass bearings on approaches to all anchorages (remember, this was before GPS and chart plotters). If you are looking for secluded anchorages, Street has them, but they are often difficult to enter. Street, now in his 90s, is still racing sailboats in Ireland. His website is full of good stories and advice (street-iolaire.com).

Finally, download the Navionics app, then download the individual charts for the entire island chain (navionics.com). This app provides three valuable tools: You can zoom in and view detailed charts of each anchorage; there are notes and recommendations from ActiveCaptain cruisers who have been there and have the latest updates; and the app has a tool to measure distances between waypoints, and to estimate course and distance for route planning.

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This unprecedented storm season and challenges from Covid-19 did not stop the Salty Dawgs from making their way to paradise in the annual Salty Dawg Fall Rally. Fifty boats left the cold for destinations including Antigua, the Bahamas, the US Virgin Islands, and Florida. Several boats suffered some damage in this year’s big seas—everything from broken booms, to flooded engine compartments, to hand steering a thousand miles—but persevered to make safe landfall. With weather guidance from Chris Parker’s Marine Weather Center and tracking from PredictWind, Shoreside Coordinators and Emergency Response teams kept in touch with the sailors and helped guide them through repairs while underway.

Clearly, the most challenging aspect of this year’s rally was COVID 19 and cruisers’ ability to gather and to enter into foreign countries. Social distancing was the rule of the day as they navigated a safe approach to dealing with the risk. The pre-rally social activities normally scheduled for Hampton, Virginia, were suspended for the year and the usual seminars in the Hampton area were handled via webinar and Salty Dawg Advisory emails. The rally organizers and shoreside staff worked to make sure that the cruisers, new and seasoned, knew the protocols around pre-departure quarantining, PCR testing, and Antigua entry.

Entry into Antigua was handled smoothly by the Antiguan port authorities and health officers, who visited each boat before sailors were allowed ashore. Activities at arrival ports were reimagined to allow social interaction and social distancing at the same time.

Caps off to the intrepid Salty Dawgs, their crew, and their shoreside support teams!

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A boat built in 1928 has a lot of history. It has essence. It absorbs a little energy from all who sail aboard, and combines it with the spirit of the ancient trees that ultimately gave it life. It’s—in a word—magical.

Few boats reach legendary status, and the John Alden-designed Malabar schooner, Charm III, is one such boat. Completely rebuilt between 1985 and 2001 on the beach in Anguilla, she is the passion (and perhaps obsession) of owner Richard West, who bought the Swedish-built boat on England’s River Yealm in 1980, and dedicated much time and money to keeping her in fine shape. And, more to the point, keep her racing.

For many classic yachts, especially those based in the Caribbean, the Antigua Classic Yacht Regatta is a must, and so it was for Charm III. But a hurricane had other plans for the boat. In 2017, while Charm III was safely ashore in a St. Maarten boatyard (or so we thought), the island was struck by catastrophic Hurricane Irma. Winds in excess of 150 knots caused islandwide devastation, and fate played a particularly nasty trick on Charm III. Standing strong in her cradle, she bested the storm until the large yacht next to her gave up the fight and toppled onto her. The neighboring yacht took down the schooner’s masts, snapping both, and driving the top of the shattered foremast right through the teak deck.

Extricated from the chaos of the boatyard in February 2018, the 49-foot schooner was motored back to her base in Anguilla, where repairs began.

West flew to the United States and bought a massive trailer. He hired two genius French shipwrights, Tristan Rouff and Aurelio Douay, and in May, using an excavator and a crane, hauled Charm III up the beach and parked her next to his home in Anguilla (as part of the deal, the Frenchmen’s aluminum sloop, Méridien, was also hauled out for work). Sitka spruce was shipped from Alaska to England and then to the island, where two new masts were built. The deck was repaired and refastened, a new rudder built, and the never-ending job of varnishing a classic got underway.

In March 2019, in a reversal of the ­haulout procedure, Charm III was resplashed. Only this time, the 181-foot, thousand-ton interisland freighter Mutty’s Pride was used to haul Charm III off the trailer into deep water. In retrospect, a possible hard knock during the launch was the cause of the adventure that lay ahead.

With the start of the Antigua Classic Yacht Regatta just four days away, I joined the schooner on her mooring in Sandy Ground, Anguilla. On board were skipper/owner West; Anguillians Kenny Richardson, an experienced sailor, and Devon “Lava” Vanterpool, who had no offshore experience but made up for it with a cracking sense of humor; and Omari “Mari” Carty, who was new to sailing.

On Monday, April 15, we slipped the mooring an hour before sunset and set a course south of St. Barth. Sailing upwind to Antigua in strong trade-wind conditions is never easy; in fact, the island’s ­upwind location is what made it so valuable to Nelson’s navy in its historic ­heyday. Laying the rhumb line proved difficult in the heavy, wind-driven seas. Needing the power of her full genoa, staysail and main, Charm III’s lee rail was frequently under as she shouldered aside the combers at 8 knots. The first leaks were a taste of things to come. A romantic might say the old schooner was crying tears of joy to be back at sea, but by the time we reached the coast of St. Eustatius (Statia), her salty tears had turned every bunk and piece of bedding into a sodden mess.

The winds couldn’t have been fouler. Blowing directly from Antigua, they knocked us farther and farther off our course. The decision was made to pass south of Statia and sail down the leeward side of St. Kitts.

A banging below alerted us to the amount of water in the boat. With each leeward roll, water surged up the inside of the hull and lifted one of the floorboards; the banging was the board dropping back into place on the counter-roll to ­windward. The skipper started the engine, and within minutes the large, engine-­driven bilge pump had the water back where it belonged: over the side.

At dawn Tuesday, we beat through the Narrows separating Nevis from St. Kitts, and again were forced from our course by the bullying wind and the North Equatorial Current, driven hard by a mocking full moon. Thoroughly soaked, battered, and unable to cook or serve hot drinks due to a stove malfunction, the crew battled on, with morale remarkably high. Halfway between Antigua and the coast of Nevis, the skipper called for a tack, but it was futile as the wind and seas again drove us back.

Work on the boat in Anguilla had left large amounts of wood shavings and construction debris in the bilge, and though the bilge had been cleaned afterward, the washing-machine conditions dislodged hidden nuggets that continually blocked the strum box—the strainer over the pump’s intake valve. Whichever tack we tried, the cloud hovering over Antigua remained in the same place. At 1600, the skipper furled the genoa, and we began to motor-sail toward our goal.

Then we began to sink.

With a report that the floorboards were almost awash, the strum box was once again hauled from the depths of the bilge. Only this time, it was clear. I took the wheel, and the skipper went below to investigate. His shouts and curses carried above the noise of the wind and seas. The mighty engine-driven bilge pump had been torn from its mountings and was beyond repair.

Fortunately, we had a large hand-­operated bilge pump. Unfortunately, it failed after a few strokes, the rebuild kit lying forgotten in storage in Anguilla.

They say nothing moves water faster than a scared man with a bucket, but there is only so much a wet and frightened ­person can do before fatigue takes over. And of course, the way our luck was going, the handles might come off the buckets. Capt. West admitted that he was considering the last resort: put out a call for help.

To ease the strain on the yacht, we ran off downwind. News from the bucket chain below was they were keeping ahead of the flow, and remarkably, after 20 minutes, they reported that the bilge was almost empty. Our call for assistance was put on hold and, running downwind under reduced sail, at 2200 we rounded the ­bottom of St. Kitts into calm water, intent on docking at Christophe Harbour Marina. But when no one at the marina answered our repeated calls, we anchored outside, set the watch, ate cold food, and slept.

Where would we be without ­cellphones and the internet? While the crew slumbered like dead men, the captain’s wife, Maryse, and daughter Mirabelle organized an emergency haulout at the St. Kitts Marine Works on the island’s northwest coast. Dawn on Wednesday saw us jogging north, and by 1100, the boat and crew were ashore in the shadow of historic Brimstone Hill among the dust and wandering goats of the boatyard.

Drying out in the tropical heat, Charm III gave up her secrets. Two seams aft on the port side, low down by the garboard, were open.

Having cleared customs, the skipper went shopping and returned with a massive electric bilge pump, a sheet of plywood, half a dozen boxes of ­drywall screws and a gallon of roofing tar. Working late into the night, Charm III’s suspect seams were “tingled,” and by 1100 the following day, Thursday, she was back in the water and heading south.

And the leak returned. Not as bad, but bad enough.

Without a doubt, the seams we patched had been letting in water, but in the darkness and the tumbling seas, while cold, wet and hungry, had we missed something obvious? Burrowing under the quarter berth, a mission in itself, Kenny Richardson found the problem. Deep below the engine, which in Charm is fitted backward, the dripless shaft seal was spraying water with every turn of the prop shaft. The bellows keeping pressure on the seals had slipped or lost their tension.

I have a strong stomach and rarely get seasick, but I doubt I could’ve spent three hours head-down under the engine, amid the reek of stale diesel and old boat, to ­repair that seal. But while Charm III, while hove to, pitched and heaved in short seas, Richardson and Vanterpoole did just that. From down below came cries of “Up the road, skip, up the road!”—which meant we were now Antigua-bound.

Or did it?

The skipper put it to a vote, saying, “Should any man have doubts, we’ll turn north for Anguilla and home.” All voted yay, in favor of Antigua. The last vote fell to me.

“No,” I said, to cries of despair. “First we push the boat hard for four hours and, if all remains well, only then should we set a course for Antigua.”

There were no dissenters. No mutiny.

Four hours of hard sailing became eight; eight became 10. Off the tip of Guadeloupe, we turned north on course for Antigua, and at 0900 on Friday, April 19, dropped anchor in Antigua’s Falmouth Harbour as the fleet of magnificent classic yachts sailed out for the first race.

Waiting in Antigua was the rest of our crew: the skipper’s wife and daughter, the two French shipwrights, and Anguillian Starlin Rosario. Again working into the night, we prepared Charm III for racing, and although we’d missed the first day’s competition, we won the following three to emerge victorious in the Vintage Schooner Class—an achievement made possible by a remarkable boat, skipper and crew.

We flew back to Anguilla and a hero’s welcome led by a throng bearing bottles of champagne and bouquets for each of the crew. Local media gave us celebrity treatment, and a huge sign on the airport road told of the latest exploits of Anguilla’s famous schooner and island crew. As for Charm III, the legendary classic that had just become even more of one, we left her in Antigua having her seams tickled. I only hope the return voyage to Anguilla is a little less hectic. I won’t be making that trip!

Postscript: Shipwrights in Antigua confirmed that the seams we “tingled” had been leaking, probably due to the bump the boat suffered aft when relaunched. However, the leak was only minor, and the main problem was certainly the dripless shaft seal. Replacing the shaft seal on Charm III entails removing the engine, but the above incident, which could have cost us the boat, or worse, proves that the words “fit and forget” have no place in a yachtsman’s vocabulary.

Journalist, photographer and broadcaster Gary Brown resides on the French side of St. Maarten. His books include the action-­adventure novels Caribbean High and Caribbean Deep, and the nonfiction work Biscay: Our Ultimate Storm, all of which are available on Amazon.

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Living on an island in the West Indies that boasts 365 beaches (“One for every day of the year!”), Martin Dudley has it pretty good.

His family came to Antigua in the late 1960s, and for the most part he’s called this place home. But aside from the tropical waters and the warm trade winds, Martin’s seen the island change substantially over the last 50 years. From English colony to fledgling country, lush mangrove forests to five-star hotels, Martin’s witnessed a country that’s undergone political and environmental disruption.

For Martin, his journey from sailor to environmental watchdog started at an early age, when he grew up in Fitches Creek, an area on the northeast side of the island where he sailed a 10-foot Mirror dinghy after school.

With a big red sail and a consistent onshore breeze, his mother never worried that Martin would get into any trouble. Later, Martin would join the Thursday night races organized by the famous local cruiser Jol Byerley, who passed away just last year.

After local races came years of sailing in Antigua Race Week before realizing that saving the marine environment was a much more serious cause than racing boats.

But it wasn’t until 2008 that Martin took his connection with sailing and merged it with an environmental philosophy.

After purchasing a 36- foot Carriacou sloop, Martin created Zero Waste Antigua, an organization to engage restaurants, marinas and the government in taking notice of the plastic waste accumulating all over the island. The initial mission aimed to take the message around Antigua and spread it to surrounding islands.

Although Martin no longer has the boat, the message stayed, and the mission of Zero Waste Antigua has flourished. Armed now with a trusty ’94 Land Rover, Martin is a staple around the island, where he can be seen collecting anything and everything that can be recycled.

What’s exciting about Martin is not that he provides a much-needed service (there’s no curbside recycling in Antigua), but that he’s educating and setting an example for other sailors and locals to follow. Single-handedly, he’s creating a green economy.

Eventually, he tells me, the goal is to find another boat that can take his message to other islands. Until that time, his Land Rover is doing the job just fine.

Tyson Bottenus, Sailors for the Sea

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Horizon Yacht Charters

Sailing for Fun is a new style of trip offered by Horizon Yacht Charters in Antigua, with the goal of getting newbies aboard 40-foot skippered Bavarias.
Opportunities for swimming, snorkeling, and beach-time are budgeted in to the four-day itineraries. The trips cost $630 per person based on four clients sharing two cabins. Price excludes provisions and fuel. Dining is a mix of onboard cooking and meals ashore.

“We’ve developed this package for people who are already vacationing here and are tempted to try sailing for the first time,” says Jackie Ashford, director of the company’s Antigua base. “This gives them a fun experience with complete flexibility built in. The first anchorage is less than five minutes from the base, and the sunsets are pretty spectacular.”

Learning is informal; captains are certified instructors who teach the curriculum of the American Sailing Association.

“The premise behind the package is to inspire people to get sailing, to do something that perhaps they’ve never done before but were always curious about, and to have fun while learning and absorbing life aboard,” Ashford says.

The charters can start on any day of the week, and must run at least three nights. Guests board the boat at the Horizon Yacht Charters base at Jolly Harbour, on the west coast of the island. For details contact the company at info@antiguahorizon.com.

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