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.

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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.

The post What are the Best Anchorages in the Caribbean? appeared first on Cruising World.

It was 0730. The sun was struggling to climb above the clouds that cover the mountains surrounding the roadstead anchorage off the village of Sainte-Anne, on the island of Martinique. Another warm day in the Caribbean. The trade winds were blowing, keeping the 200-plus sailboats anchored there all aiming in the same direction.

I had just come into the cockpit of Dove—a 54-foot Crealock sloop that I was boat-sitting for a friend—with a bowl of fresh fruit and my coffee when I heard the familiar buzz of a 10-horsepower outboard approaching. A young French couple was heading toward me with the rest of my breakfast.

“Bonjour,” I shouted as their 10-foot inflatable came alongside.

“Bonjour,” they both replied. Guerric, a tall, thin man in his late 20s, stood up to grab the cap rail. His companion, Juliette, sat on the dinghy’s pontoon, crammed in among plastic tubs of baguettes and pastries. “What will it be today?” she asked in her accented English.

“A chocolate croissant,” I replied. “And a baguette for my lunch.” Juliette removed the cover to a pastry tub, slipped my breakfast into a brown paper bag and handed it to Guerric, who then handed it up to me along with a long baguette.

“I’ll be right back,” I said, diving below to paw through a pile of coins on the chart table. The baguette they sell me each morning is 1.90 euros, the croissant 1.50. I could get both cheaper in the village, but that would mean getting dressed, lowering the dinghy, firing up the engine, speeding into town, finding a spot at the overcrowded dinghy dock, locking the security chain to a cleat, walking through the village, then standing in line at the boulangerie with a dozen others. Then, it’s all the way back to the boat. Forget the expense. The service Juliette and Guerric provide each morning is worth the markup.

Besides, after two weeks here, alone, among hundreds of French yachts at anchor and a village full of French tourists, they were the only two I could converse with in English. So we would chat.

Guerric and Juliette are both from Lyon, France. He was a chef and she was teaching school until they both took off the previous fall for a yearlong adventure. Since neither had much sailing experience, they couldn’t find a boat to sail on to cross the Atlantic, so they flew to Guadeloupe. From there they joined a catamaran heading south. In Tobago Cays they met a chap on a small boat making the rounds of anchored yachts selling stuff. That got them thinking.

With the Sainte-Anne anchorage chock-full of liveaboards, and transit and charter yachts, there was a ready market for a morning pastry-delivery service. The couple bought a dinghy and engine, rented an apartment with a large stove, and set up shop. Their business card reads: “Mado—Artisans Gourmands.”

“So, you make all these things?”

“No,” Guerric said. “We buy the baguettes from the boulangerie in the village.”

“But we make the croissants ourselves,” Juliette added.

“What does that entail?” I asked. Guerric and Juliette looked at each other, and she giggled.

“I get up at 2 in the morning,” she said, “to prepare the croissants. We use frozen pastry that has to be thawed, filled, rolled, and brushed with butter. Then Guerric gets up, and he does the baking.”

“So the croissants are freshly baked?”

“I make 85 croissants every morning.”

“Is it working?” I asked.

“Yes, it is working,” said Juliette. “We are very happy.”

“So, you make a living at this?”

“Yes, we can pay all our expenses, the cost of our travels, and save some for the future.”

“How long have you been doing this?”

“Since December.”

“Every morning?”

“Every morning. Except if it’s blowing too much or raining.” Juliette said.

Guerric, I learned, studied journalism before landing a job as a chef. Juliette is a few years younger. Their English is very good. They are a couple but not married—yet.

“We are using this year in the Caribbean as an adventure, to see if we are ‘compatible.’”

“It’s like you’re taking your honeymoon before the wedding,” I said.

They both nodded and laughed.

“What’s in the future?” I asked.

They looked at each other, and laughed again.

“Who knows?” Guerric replied.

“We love the restaurant business,” Juliette added. “We hope to find a boat that will take us north to Saint-Martin in the spring. Or maybe Cuba.”

“Will you come back here?” I asked. Sainte-Anne needs someone to carry on this morning ritual. The two looked at each other and shrugged.

If you spend any time in these parts, you’ll find that these two are not the only floating entrepreneurs in the island chain. My friend Larry, who owns Dove, sailed up and down the Leewards and filled me in on a few others.

“There are lots of harbor entrepreneurs,” Larry wrote. “Bequia has excellent croissants brought to your boat by a very nice young man, and they are delicious. Better than I get in France. Carriacou has always had a guy making the rounds, selling wine and oysters, while on Saint-Martin, they not only bring croissants out to you, they can fill up your water tanks. An old West Indian in Rodney Bay sells vegetables and fruit from his overstuffed rowboat. In the BVI,” Larry added, “a couple comes around selling fruit and vegetables from their own garden, as well as fresh eggs from HM Prison! It’s stamped right there on the box. In Tobago Cays, someone sells bread, baguettes.”

“We have to go,” Juliette said. “We have lots more boats to visit.” Off they went in their dinghy, waving.

“See you tomorrow,” I shouted, with a wave.

Juliette waved and shouted back, “Bonne journée, à demain!” (Have a good day, see you tomorrow!)

I sat down at the cockpit table, with my croissant, pineapple and coffee. Life is all possibilities for those two, I thought to myself. I too was there once. Heck, I’m there now.

David Lyman spent three months during the pre-pandemic winter of 2019-20 in the Caribbean moving from island to island while boat-sitting for a friend and writing. He is currently back home in Maine.

The post The Floating Bakers of Saint-Anne, Martinique appeared first on Cruising World.

During press events at the Miami International Boat Show, The Moorings, MarineMax Vacations and Dream Yacht Charter announced new destinations for vacation sailors:

The Moorings, now in Martinique

Great trade-wind sailing with French flair? Yes please! The Moorings announced Martinique as their newest destination. Bareboat and skippered charters aboard sail and power yachts are open for booking now for winter 2019 departures. Located in the heart of the Windward Islands, Martinique is a mountainous island and a mecca for French-Caribbean culture, maritime history and world-class sailing. The Moorings base is at the modern La Marina du Marin, which is about 45 minutes from the international airport.

Nicknamed the Culinary Capital of the Caribbean, Martinique is a cultural melting pot that blends cosmopolitan appeal with island charm. “From hiking through lush rainforests to bathing in natural hot springs, strolling on black-sand beaches to feasting on French and Creole cuisine, this one-of-a-kind destination is worthy of every traveler’s bucket list,” says Josie Tucci, vice president of sales and marketing for The Moorings. For more information, visit moorings.com/martinique.

MarineMax Vacations expands to the Bahamas

MarineMax Vacations, which is based in the British Virgin Islands, has selected the Bahamas to expand their charter operation. The new base will be located at the Abaco Beach Resort, which is located at Marsh Harbour, and easily accessible with flights from Palm Beach, Fort Lauderdale or Miami to Marsh Harbour International Airport. “We are proud to be working with this iconic resort to bring catamaran charters to a new audience while opening up the opportunity to have a change of scenery for those who know MarineMax Vacations,” says Raul Bermudez, vice president of MarineMax Charter Division.

Guests can choose from a variety of power catamarans ranging from 36 to 48 feet or a sailboat through one of MarineMax Vacations’ partner charter companies. For more information, visit marinemaxvacations.com.

Dream Yacht Charter brings Dream Boat Club to North America

And for something a little different, Dream Yacht Charter announced that they are bringing their Dream Boat Club to North America. Different from the yacht-charter side of the business, Dream Boat Club is a membership-based program that offers use of a variety of boats in multiple locations. The club is based off the earlier success if its European model, and is a reflection of today’s growing sharing economy. Upon joining, Dream Boat Club members receive training on boat handling and then simply have to schedule when they would like to use the boat. Membership dues cover all maintenance, mooring and insurance fees as well on fleets of newer, well-equipped boats. The company plans to have locations throughout the US and Canada in the near future. Learn more at dreamboatclub.com.

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“Allez allez, allez allez,” come on, come on, a very wet fisherman in pink shorts, camo shirt and bright-yellow ball cap chanted like a drill sergeant at a parade. Alongside, a snaking line of a couple dozen equally drenched sailors grabbed a green poly line, dug heels in the sand and threw ourselves backward, pulling in a surprisingly small length with each lunge.

The rain poured down, and from time to time, the singsong chanting was accompanied by the blare of conch shells blown by fishermen farther down the beach. “Allez allez! Toot-toot!” Inch by inch, we pulled on the rough line until finally we came to the beginning of the lengthy net that was stretched across the harbor at Petite Anse d’Arlet, a small village on the southwest coast of Martinique.

Now the real work began. Our crew — French, English, Americans, Russians, you name it, all from the Fountaine Pajot catamarans anchored in the next harbor to the north — split up, half grabbing ahold of the top of the net, the others, the bottom. “Allez allez!” We pulled and pulled, fingers caught up in the webbing. Soon, feet were tangled up too as we slowly gained on the work before us and the seine net piled up on the sand.

It was early, about 0630. The hour and the torrential rain kept the streets behind us empty. The beach, though, was a flurry of activity as fishermen shouted orders in French and madly blew their conchs, communicating with the men tending the net from their pangas and the divers with masks and snorkels, who swam inside it as we pulled it ashore.

At last, a half-hour or better from when we started, the end was in sight. At first, we’d pulled in only empty netting, but as it began to tighten along the water’s edge and the swimmers were now able to stand, fish roiled the water. Bins were carried down to where we worked, and the fishermen waded in to grab their catch.

The day before, the 28 catamarans taking part in the Fountaine Pajot Owners Rendezvous had raced north from Le Marin and stopped at Petite Anse for lunch, local color and a swim with the turtles before heading off around the headland to anchor at Grande Anse for the night. This morning, the 25 or so of us who’d risen in the dark and abided by the rain to catch a bus back here for the traditional seine fishing watched as those same turtles were grabbed by the wading fishermen and tossed free. The sardines, snappers and pufferfish were not so lucky. With the net now on the sand, they were scooped up quickly. When the last flopping fish was in a tub, they were carried up the beach to where a set of scales had been set up on a nearby wall. By now, the town had woken up. There were cars and people coming and going, and the fish store, such as it was, was open for business.

And so was the rum tasting, put on by tourism authorities and Habitation Clément, a well-known island distillery. A gregarious crowd of local officials, fishermen and sailors gathered to sample the wares. Our drill sergeant had a small glass of rum tucked neatly into the pocket of his T-shirt. The more he and his mates sipped, the more frequently they blew their conchs. Merriment, rum punch and fish cakes for breakfast — what a way to start the day!

Actually, each day of this little Caribbean adventure turned out to be pretty excellent. The rally was organized by the French catamaran builder to bring its far-flung owners together for four days of sailing and parties in a location where fun was absolutely guaranteed. The fleet was a mix of privately owned vessels and charter boats, such as Guiriden, a Saona 47 we’d picked up at the Dream Yachts base in Le Marin a couple of days before the official party began. Driving our bus was CW’s advertising director, Ted Ruegg, and his wife, Heide. Calling tactics, if we needed them, was their Annapolis, Maryland, sailing pal Dave Robinson. Photographer Jon Whittle and I were on hand and determined to work and play, in equal measure.

Since we had the boat for a week, we planned it so we arrived in Le Marin a couple of days ahead of time. We flew in on Tuesday, and spent the rest of the day and Wednesday morning taking care of shoreside formalities, such as provisioning and Dream’s boat and chart briefings. Then it was time to get to work: Dutifully, we went sailing.

A Dream captain moved Guiriden from its slip and then turned the wheel over to Ted. We motored out to Pointe du Marin, where Club Med has a sprawling resort, and from there, raised sails and bore off on a close reach, heading southeast to the tip of the island. Near shore was a minefield of lobster-pot buoys, so we headed to deeper soundings before tightening up the sheets and turning east. Our destination was Baie des Anglais, a protected anchorage on Martinique’s windward coast that was well recommended at our chart briefing.

It was fine sailing, though we had a good bit of current on the nose. Eventually, our course took us closer and closer to the wind, and after a tack or two, we started the engine and just plowed into it until we reached the narrow unmarked channel leading into the bay. Surf pounded on the rocky islets on either side of us. Standing nearby Ted at the helm, I kept a close eye on the iNavX app on my phone so that we stayed in deep water. Inside, it was a millpond. Though we could see breaking waves behind us, the water was flat calm, and we were surrounded by nothing but rolling green hills and mangroves lining the shore. Better yet, we had the place all to ourselves. We swam in the brackish water, sipped and dined in fine style, and that night sat on Guiriden‘s trampoline and spotted both the Southern Cross and Polaris in the clear, dark sky.

Passing squalls made for lively sailing conditions, but they were spectacular to watch as they rolled over the hills.

On Thursday, we had time for a little paddleboarding and swimming in the morning. Then, around 1100, a breezy squall passed by, taking every breath of wind with it. Instead of a lovely downwind run home, it was a motorboat ride back to Le Marin for the start of the week’s official fun.

Back at the marina where we started, rally check-in and a skippers meeting took most of the afternoon, and was followed by an open-air rum tasting and cocktail party just before sundown. That evening, we were all on our own for dinner, but the crowd tended to migrate to the casual seating and tasty dishes at L’Annexe. The place was packed and the evening lively, but with an 0800 departure and two races planned for the next morning, Team Guiriden sensibly retired (sort of) early.

The rules for the Friday-morning short around-the-buoys race, to be followed by the Cruising World Rally to les Anses d’Arlet, were simple: Leave the committee boat to starboard, the pin to port; pass between Diamond Rock and the mainland on the way north; and any boat over the starting line early would be penalized and have to buy every other boat drinks. Thank heavens they didn’t say anything about collisions.

The wind at the start of the buoy race was light and puffy. The course called for a short upwind leg, followed by a couple of reaches across the bay and back to the finish. The rally had attracted crews with vastly different sailing skills. There were Fountaine Pajot founder Jean-François Fountaine and his wife, Claire, the president of the company, both world-class sailors; then there were the folks we saw on the plane studying their learn-to-sail textbooks. The result, in the first race at least, was spirited competition at the front of the pack and a parade of boats behind. It was a pretty sight to see all those sails stretched out over a mile or two of deep blue sea.

The rally proved a bit more interesting, when the breeze stalled just after the start and again just before the finish. Let’s just say new acquaintances were made on each occasion. But in between the first short windward mark and the finish line off Petite Anse d’Arlet, we had arguably some of the best sailing of the week. The wind was well aft of the beam as we bore off toward iconic Diamond Rock. On Guiriden, we winged out the genoa, leading the loaded-up sheet to a cleat amidships. For our shutterbug, Whittle, it was one of his Kodak moments when the cats neared the rock and sailed along the bold Martinique shore, clouds and their shadows dancing across the mountainous terrain inland.

In Petite Anse, we crossed the finish line, anchored and piled into the dinghy to go ashore. What a lovely little village, with its church located at the head of the pier. In a pavilion just to the left, local craftsmen and artists had set up shop. There was rum to be tasted, and traditional dancers — young women dressed in full-length white dresses with colorful calico shawls, and men in white suits with bright-red vests — swirled to lively Caribbean tunes.

After a spell, Whittle and I wandered off to see the backstreets of town. We found well-kept houses with neat yards, many brightly painted in yellow, blue and other calico colors. Eventually, our wandering led us to the Coco Cafe and a table on the beach under a shady tree. The local specialty was the Coco Punch, a concoction of coconut water and rum that was as soothing as it was delicious.

Back at the boat, we squeezed in a quick swim with the turtles, then motored the short distance around the bold point to Grande Anse, an equally lovely bay and beach where there was plenty of room for the fleet to spread out and anchor.

Ashore at Ti Sable, a beachside restaurant with boothlike tables covered by flowing white canopies, the sun had just set and cocktails were being served when all of a sudden there was a commotion. The reception area filled with metallic-colored men and women, some bearing torches, some dressed in ragged outfits, others bare chested. Moving slowly, they struck and held haunting poses, not even blinking, for what seemed like minutes at a time.

And then, like that, they were gone. Whoa, what was that?

In fact, it was les Hommes d’Argile, a local dance troupe that was honestly quite amazing. It was a tough act to follow, but grilled lobsters, local vegetable dishes and music into the evening gave it a good try.

Squalls rolled through overnight. While the rest of the crew slept in, Whittle and I were up at 0545. There was just one other inflatable on the beach when we arrived on shore for the fish-seining adventure, and at first, we wondered if it had been called off. Soon enough, we heard the motor of another dinghy start up, then another. In the end, it was a small but hardy group that set off to help harvest the day’s catch.

After the morning’s adventure, we returned to Guiriden fortified by a pleasant rum buzz and ready for the race back to Le Marin. The breeze was quite light, so we followed the lead of cats leaving before us and motored southward. A half-hour later, though, the VHF radio crackled to life and the race committee announced the breeze was up and the race to the anchorage by Club Med was indeed on. We had five minutes to find the starting line. We scrambled to hoist sail and barely made it in time. The wind, of course, immediately died, just about the time the heavens opened up anew.

As Guiriden approached Diamond Rock, the skies at last cleared and a fresh breeze — on the nose — filled in. We rode a starboard tack toward shore, then tacked out, certain we’d clear the rock.

We didn’t. Instead, we continued on out to sea before tacking again toward shore, certain we’d clear the rock this time.

We didn’t.

Nor did we leave it behind the third, fourth or fifth time. The current that once made the rock an important British military outpost refused to give up its grip on us. To be honest, we were getting pretty sick of the darned rock, and the wind was dying to boot. Under the threat of mutiny, or worse, drunken mutiny, Ted relented, started the engines, and we motored the remainder of the way. To a person, no one wanted to miss the reception, dinner and festivities that night at Club Med.

Sunday was the final day of the rally. In the morning, a powerboat towed three yoles to the beach, where they were pulled ashore by their crews. The yoles are traditional Martinique sailing and fishing skiffs. Each boat was 30-something feet long and rigged with a single mast made from the trunk of a tree and a square sail and gaff. Underway, boards are wedged into the opposite gunnel and the crew hikes out on them to windward. To tack, the boards are reset on the opposite side. Every summer, a fleet of them races around the island in Le Tour de Yoles Ronde Martinique, an eight-stage, 110-mile contest.

Once rigged, each yole had a local captain and carried a dozen or so crew from the rally. It was gusty, and the boats took off like a shot. We chased them in our inflatable/photo boat, but couldn’t keep up, though we did cut them off when they tacked. We even followed along as they cut through a seemingly impenetrable grove of mangroves into an adjacent little bay filled with all manner of craft tied to the shore, and a pirate ship at anchor, complete with a crew who, when they saw us coming, brandished sabers and a cannon. It was quite the little aquatic village.

Back out in fresh breeze, the yoles took off across the bay for one last spray-flying ride before returning to the beach. As the crews derigged the boats, the rally came to its official close. It had been an action-packed few days, and goodbyes were heartfelt. But for Guiriden, there was still some fun to be had.

Returning to the marina for a few supplies, we picked up Dan Lockyer, general manager of Dream Yachts in the United States, and then set off northward once again, this time to Anse Mitan, a lovely beach and bay a bit farther north than our travels had taken us previously. We had good wind behind us as we barreled up the coast, first on a run, then a reach and finally closehauled as we headed for the beach, where we anchored in about 20 feet of water. After days of set schedules and bustling activities, a relaxed swim; the sunset over Mount Pelee, Martinique’s towering volcanic peak; and dinner aboard were most welcomed. It was definitely lights out by 2300 for this crew.

Despite a rainy start to Monday morning, we took the dinghy ashore to the nearby public beach and left it tied to a tree. From there, it was a short walk into the village at Trois-Îlets, a popular tourist spot with restaurants, galleries and shops. We explored the town. Then, when a particularly wet and prolonged squall rolled through, we explored Carol’s, a circular bar with wide canvas awnings, a friendly atmosphere and giant mojitos.

By lunch, we were back on the boat with the bows pointed south. Once again, the rain had robbed us of wind, so we gave the batteries a good recharge. By the time we were anchored in Ste. Anne, a small community just south of Le Marin, the sun was out and skies were blue. Whittle and I took one last walkabout ashore. As at Petite Anse d’Arlet, a lovely church stood at the head of the pier. On the dock, there were families fishing, and ashore we found a sleepy little town, where the people could not have been friendlier. When it turned out one shop didn’t sell ice, the proprietor walked us down the street to one that did.

On every charter trip I’ve been lucky enough to go on, there’s been something remarkable about that last night on the boat. Anchored in Ste. Anne, it was the golden hills at sunset, the warm night air, dinner with friends and conversations that went well into the night. It wasn’t just a happy ending, it was perfect.

Mark Pillsbury is CW’s editor.

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One of the things that makes the Windward Islands such a fantastic place to sail is the wind — it’s always blowing, or at least it has been the three times I’ve visited. Friends and I have bashed our way northward between islands, sailing hard on the breeze in big open-ocean swells, and we’ve surfed down waves with the speedo pegged in the teens while reaching south. Even in the lee of the islands, where the water’s flat and the breeze might go dead-calm, the crew has been kept on its toes by gusts that can come barreling down the valleys from the mist-shrouded peaks at any moment.

Those glorious trade winds came on with a vengeance one day last winter as five pals and I sailed south along the coast of Martinique aboard a Moorings 5800 catamaran, bound for St. Lucia. With the anemometer hovering in the mid-30s, it was a day better suited for a snug harbor and snorkeling, but we were set to fly home to the frozen north the next morning, so like it or not, our boat, Double D, had to be returned to its base in Rodney Bay.

Had I been the one on the wheel, my knuckles would have been white, for sure. Instead, as the puffs came on and the apparent wind pushed 50 knots, my fingers clutched an ice-cold brew and I sat back to enjoy the ride, confident that Capt. Cosmas Elibox — “Cosy,” as he liked to be called — had it all under control. Welcome to the pleasures of a crewed charter.

This little adventure came together at the suggestion of The Moorings general manager Josie Tucci. Why not, she said, join her in St. Lucia aboard the six-cabin 5800 for a sail up to Martinique to check out the rum-distillery tours the company was about to launch?

Why not, indeed? We brought along photographer Marianne Lee to chronicle our investigative-reporting efforts, so that still left two more cabins for guests. Josie invited along Nick Crabtree, a racer who works with Pindar International and handles logistics for the Volvo Ocean Race and other grand-scale regattas. I tapped hometown friends and sailors Tom and Kathy Famulari, who’d recently been smitten by the Caribbean during a bareboat charter of their own.

Besides finding flights to get us to St. Lucia on a Saturday afternoon, the biggest concern before the trip began was where we’d be able to watch the Super Bowl the day after we arrived in the Caribbean. Tom, Kathy and I are from New England, after all, and the Patriots were shooting for another victory and Tom Brady’s fifth championship ring. Missing the game wasn’t an option.

We needn’t have worried; Cosy had us covered. But we’ll get to that in a minute.

At the start of our adventure, we arrived dockside too late for our planned Saturday departure, so we made the most of our first evening in the Caribbean by getting our charter briefing out of the way and settling in aboard Double D. Our orientation involved rounds of rum punches, followed by a fine dinner of steaks, veggies and spuds, washed down by a delicious malbec. Chef Dekoda “Vicky” Dowers immediately impressed us with her culinary skills, learned on her home island of nearby St. Vincent and honed by years of practice in the charter trade.

First thing Sunday morning, Cosy collected our passports and headed off to customs to take care of paperwork. Josie took the opportunity to stretch her legs on a little run accompanied by first mate Brad Gangardine, a strapping and handsome lad who kept the ladies highly entertained and answered our every food and drink request with a gleaming smile. I walked a similar route toward Pigeon Island National Landmark, a hilly park on St. Lucia’s northwest coast. Sunday is play day for St. Lucians, and traffic was brisk with cars and pickup trucks full of beach-bound families. Along the roadside, horses searched for morsels in the scrub brush, and roosters, seemingly everywhere, crowed incessantly as the sun, heat and humidity soared in unison.

Back at Double D, by the time breakfast was done, Cosy had returned and we were off. Outside the marina, we paused briefly to raise the mainsail — I should say the crew raised the main; we sat back and watched — then we rounded Pigeon Point and sailed hard on the wind toward Martinique, barely visible on the horizon, 20 miles to the north.

Underway aboard the 5800, the flybridge was the place to be. The 360-degree view was magnificent, and between the helm station and winches forward, and the fridge, grill and drink coolers aft, there were comfortable couches in the shade of the bimini and lounge chairs in the sun. As the miles ticked off, Cosy and Brad, both St. Lucians, answered our many questions about island life and our itinerary over the next few days. The breeze was close to perfect, and we made good progress with a single reef in the main and the genoa rolled out. Slowly, tall, angular peaks in the center and on the north shore of Martinique came into focus, as did the broad valleys to the south, where bananas, sugar and other crops are grown.

Our destination for the day was Ste. Anne, a lovely village on the south coast, and Le Marin, the harbor next door. Cosy never considered firing up the engines to get us in faster. Instead, we approached by sail, tacking right up until we reached the harbor, where we were met by Club Med kite- and windsurfers out enjoying the brisk trades and flat water.

Once anchored, our attention turned to game-day preparations: tasty hors d’oeuvres, and rum bombs to wash them down. Then, with evening approaching, Cosy ferried us ashore. As luck would have it, right in front of us we found Mango Bay, a friendly, open-air restaurant with a television tuned to a French sports channel showing guys tossing a football around the studio.

Kickoff was imminent, so we grabbed an open table right under the screen and discovered we were surrounded by several other spirited Yanks from the anchorage. Most were New Englanders, and like us, they must have been tempted to keel-haul the lone loud and strutting Falcons fan. He took delight in taunting us repeatedly throughout the first half as Atlanta put point after point on the board, and then sat stunned and thoroughly humiliated when his team choked it up big time in the second. Go Pats!

Let the Tours Begin

Monday, the islanders went back to work, and so did we. Breakfast was served early, then the six of us were shuttled ashore to briefly explore Le Marin’s waterfront while waiting for a van to take us to our first distillery, Habitation Clément, a spectacular sugar plantation in Le François, on the island’s east coast. The buildings and surrounding grounds have been restored as an interpretation center of Creole culture.

To get there, we snaked through groves of banana trees, their fruit covered in sacks to keep away the insects, and across broad, green valleys dotted with the occasional village. Up we climbed over the island’s mountainous spine, pausing at the top for a view of the inlets below that are protected from the boisterous Atlantic by offshore reefs.

At Habitation Clément, we rented headsets that provided an English-language self-guided tour of the plantation and we set off down the path from the visitors center. At each stop along the way, we paused and listened: The sprawling fig tree was once thought to house evil spirits; towering royal palms were a refuge for migrating birds; a story accompanied each of the many sculptures created by local artists. We visited the plantation’s working sugar-cane fields, then climbed the hill to see the vats and rugged machinery used in the distillery process. At one building, we stuck our heads into the dark interior, where hundreds of casks of aging rum were stored. In the tropical heat, up to 10 percent of their contents will evaporate through the wooden barrels in a year. After only a few breaths, we made note of having a good buzz going as we stepped back into the sunshine.

Atop the hill sat the plantation house and its outbuildings. A plaque pointed to the rooms where U.S. President George Bush and French President Francois Mitterrand met in 1991 at the end of the Gulf War to discuss the future of Kuwait. Inside the main house, fine antiques filled each room. A refreshing breeze blew through the open windows, and wooden shutters kept the rooms shaded and cool in the hot tropical sun. Afterward, sitting in a finely crafted gazebo and enjoying the breeze that funneled up the valleys from the sea,

I couldn’t help but think that while this would have been a spectacular home for the plantation’s founder, Charles Clément, it was a very different existence for workers who harvested and milled the sugar.

The Clément distillery closed its doors at this location in 1988, when operations were moved to a new facility a short distance away. Restoration of Habitation Clément began in 2005 and is ongoing.

Modern Martinique

After a trip to the tasting room, we left Habitation Clément, toting bags filled with bottles of their finest, and boarded our van for Fort-de-France, a bustling port city on the west coast and Martinique’s capital. The winding mountain road soon turned into a modern four-lane highway flanked by office buildings, houses and shopping centers. Our driver took us to the downtown marketplace, a sprawling indoor collection of stalls, where vendors hawked fruits, vegetables, tangy Caribbean spices and colorful calico shirts and dresses.

For lunch, we climbed to the second floor of the market and chose Mamma’s Shack, one of several restaurants where the maitre d’s jostled aggressively for customers. The menu was strictly local. I ordered goat, cassava beans and rice, and we all shared a helping of cod cakes doused with hot sauce.

Afterward, we did a drive-by of Fort Louis and the waterfront. We looked across broad Fort-de-France Bay to the anchorage where we’d spend the night. By boat, it might have been a quick trip, but a good chunk of the afternoon was spent on the highway as we skirted the shore. Our journey ended in Trois-Îlets, a lively little tourist town of beaches and shops, where Cosy and Brad were waiting for us with the tender.

Double D was anchored just around the corner, at Anse Mitan. It was tempting to swim to shore to investigate the beachfront resort, but instead, we all jumped in and paddled about the boat. Cosy fired up the massive speaker he kept stashed below the saloon table, and so with reggae tunes blaring, we floated on foam tubes and enjoyed a cold beer or two.

Monday night was a beauty. We sat up on the flybridge, enjoying the night sky and the view of lights on the hills overlooking the city.

So far, this had been a fine vacation, but Marianne and I were on the clock, so to speak; I had a story to write, and she needed photos. So, bright and early Tuesday morning, the crew hauled anchor and motored a short way to Anse Dufour, a perfect little horseshoe-shaped cove with a white-sand beach at its center and three colorful little cottages just behind it. The hills rose steeply up from the beach, and gusty winds poured down them. There were fishing skiffs hauled up on the sand, and a handful of folks swam near shore.

When the sun was right, Cosy used a spare halyard to haul Marianne and her cameras up the mast to the first spreaders. Kathy and Tom enjoyed the morning on the foredeck, while I paddleboarded around the cove and Nick and Josie went exploring by kayak. Before long, day boats carrying snorkelers from the nearby resorts arrived and the anchorage became downright crowded. Between swimmers and katabatic gusts, paddling became a lot like work, so we traded board and kayak for masks and snorkels and joined the crowds in the water.

Tuesday afternoon we again set sail, this time heading farther north up the coast to St. Pierre, the northern Martinique town that was wiped out when volcanic Mount Pelee blew its top in 1902, killing nearly 30,000 people and leaving just two survivors. Thirty-plus knots of wind sent us scurrying along on a comfortable reach at 9 knots and better.

When we arrived, Pelee’s summit was covered by clouds, as it almost always is. The hillsides were rich and green-looking, thanks to all the rain that falls there. Ashore, we wandered the streets of the once-again bustling town, where evidence of the deadly eruption can still be seen on the blackened walls of many of the buildings.

Cruising boats — including many a steel vessel flying a French flag — filled the harbor. We swam off Double D‘s stern and savored the sunset on this, our last night out.

After another fine dinner from Vicky, Cosy treated us to a tasting from his collection of infused rums. Into the bottles of white rum, he’d added ingredients like passion fruit, vanilla, coffee, cinnamon, guava, coconut and island spices (my favorite). He then let them ferment for three weeks or more. I can say two things definitively: They were delicious, and we all slept soundly when our heads hit the pillows.

Another Round, Please We had one more adventure in store before our sail home. On Wednesday morning, Double D motored a short way south to anchor off the beach at Le Carbet, a small community of bars, restaurants and shops. Cosy ferried us to a pier at the north end of the beach, where an old couple stood fishing. In no time, they filled their bucket with small, silvery fish.

The six of us left the dock and walked a mile or so on the main street, following it inland until we found a sign for the Distillerie Neisson. A dirt road led us past groves of trees to a hillside sugar plantation and the distillery, which has been in operation since 1931. Unlike Habitation Clément, this was a strictly commercial concern. Red buildings were arranged around a courtyard and filled with vats, bottling machines and warehouse space. Production takes place only a few months out of the year, and the machinery was idle when we arrived. Even so, at midmorning, the gift shop was filled with people waiting to sample the wares.

When it was our turn, a lively chap and third-generation member of the family spoke broken English and used a poster on the wall to explain the rum-making process, and then stepped briskly behind a counter teeming with bottles and asked if we’d care to try some.

We did.

“You could run your car on this, mate,” noted Nick after sampling one of the more high-octane concoctions. Almost without us noticing, the rum worked its magic, as Tom, who walked into a sign on his way out, could attest.

Fortified for the long 40-mile day ahead of us, we trudged back to Double D, where, after a swim, we got quickly underway. The rhumb line to Rodney Bay took us farther and farther offshore and out of the lee of the island. Soon, we were surrounded by whitecaps, but Cosy, like Double D, took the conditions in stride. They’d seen them before. For the rest of us, it was a heck of a ride, and one I won’t soon forget.

We approached St. Lucia toward sunset — always a lovely time to be at sea — and stars filled the sky by the time the hook was finally set. There was a collective sigh as we sipped cocktails and sat down to one last meal from Vicky, glad to have the crossing over with, even if none of us had lifted a finger to make it happen. As I said at the beginning, welcome to the pleasures of a crewed charter.

Like most sailors, I’ve always found the rewards of a sailing vacation to be in the sailing itself, so spending every day aboard Double D in guest mode took some getting used to. But would I put to sea again with captain and crew? Hell, yes.

Mark Pillsbury is editor of Cruising World.

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Let me begin by stating the simple fact that I love the French Islands. They make me want to tuck a baguette under my arm, don a neck scarf and immerse myself in all things French while zipping around town on a little Vespa yelling a chipper “bon jour!” at everyone I pass.

Martinique, so far, has done nothing to tarnish this little fantasy of mine. I had no idea what to expect as we sailed into the capital of Fort de France, but I knew we were in for something different when the shoreline greeted us with clusters of buildings and a handful of high rises instead of modest wooden shacks and swaying palm trees (oh there are palm trees, for sure, but they are not the main players in this particular skyline). One quick trip ashore and immediately you feel like you have been transported to Europe. The narrow cobblestone streets, the multitude of euro-style shops sandwiched together, the grocery stores full of delectable European eats, the well-appointed parks, hole-in-the wall cafes, the unmistakable “buzz” of a city…It’s a welcome change to be able to walk into a pharmacy and find the lotion or drug you are looking for, to have a wide variety of stalls and stands from which to grab a quick (and delicious) lunchtime Panini or crepe (oh, the crepes!), to revel in the European charm and aforementioned subtleties that makes wandering the winding streets of cities like Paris, Rome or Buenos Aires (a very European city, despite its South American location) so wonderful. It is so interesting to me that each of these islands, even though their similarities abound, can be so drastically different from their neighbors in both culture and curb appeal. Just another one of the many reasons I love cruising these Caribbean islands so much, it’s never the same day – or island – twice.

When two people, with the same life long dream of sailing around the world find each other, there’s only one thing to do… make it happen!

Scott and Brittany departed in 2010 with big plans to “see the world” from the deck of their sailboat. After sailing from Chicago to Trinidad via the “thorny path”, they are now back at it with their first baby and second boat. Check out all the juice at .

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