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.

The boat lurched from side to side and our dinner plates slid from the shelves, causing them to crash to the floor. In the moon’s absence, the water was ink-black. Foreboding rocky cliffs were to starboard, appearing closer than they actually were. Having sailed 72 nautical miles from Martinique in salty conditions, my husband, Dave, our three boys and I were feeling weary and decided to put up with the uncomfortable anchorage until morning. Sleep came in fits and bursts; sunrise brought little respite from the relentless roll. Feeling more seasick at anchor than we did on passage, we made the wet dinghy ride to shore for some reprieve. We looked back in awe as Roam, our Moody 47, rolled back and forth in the swell, the rails not far from the water. The moment we reached the lee of the headland, the water smoothed, and we could finally relax. Questioning the local authorities’ motives behind why we were not allowed to anchor any closer to shore, we vowed to spend 13 euros on a mooring ball the moment one became available. For now, though, we were in desperate need of coffee and somewhere still, to sit and enjoy it.

Despite the uncomfortable start, the Caribbean island of Terre-de-Haut—known for its coral-rich waters and palm-tree-lined beaches—instantly charmed us, and our sleepless night was quickly forgotten. Located only 6 nautical miles from the ­southernmost tip of Guadeloupe, Îles des Saintes—or Les Saintes, as it’s more casually known—is made up of nine idyllic islands, of which only two are inhabited. The island group is renowned for the clarity of its waters; orange starfish could be seen resting on the seabed from many meters above. The horseshoe-shaped bay, dotted with colorful fishing boats dancing quietly on anchor, provided shelter for a field of some 80 mooring balls. The anchorage was located farther behind, marked by a row of yellow buoys. Small gray pelicans darted and weaved among the boats, searching for fish.

Ashore, gingerbread-house-like cottages complete with latticework and window shutters lined the waterfront. Their matching roofs provided the feel of a Greek island, despite their rust-red color. The smell of freshly baked baguettes and coffee wafted from the tiny waterfront cafes, and from the moment we secured our dinghy to the dock, we were captivated by the attractive village of Bourg des Saintes. Patterned sarongs and flowing silk dresses could be seen blowing gracefully in the breeze from the open windows of boutiques lining the narrow streets. We were excited to discover what this island, with its bustling shopfronts and whitewashed cottages, had to offer.

Although it was the middle of winter, the sun was warm and the sky clear. After a breakfast of croissants and coffee (after all, the islands of Les Saintes are French), we began wandering around the small village. The first thing we noticed was the absence of cars. Instead, tourists and locals alike were scooting along on electric golf carts and mopeds. Being on a modest cruisers’ budget, we skipped a rental and continued on foot. As we made our way to the northern end of the island, we passed enchanting cottages and fences covered in pink hibiscus. Hummingbirds flitted from flower to flower, drinking the sweet nectar, and curtains bellowed from kitchen windows, begging us to peer inside. Elderly women strolled the streets, selling French pastries from handmade wicker baskets.

We were curious to sample these round tarts, with their crunchy base and moist center. Filled with coconut, banana or guava jam, and topped with the softest sponge, these delicious delicacies did not disappoint. “Parlez-vous Anglais?” we asked one of the women. Demonstrating her lack of English by holding up her thumb and forefinger to make the symbol known the world over as “a little,” she told us that these tender, pillowlike tarts were called tourment d’amour, meaning “love’s torment.” In broken English that was far better than my French, she told us how the women of Les Saintes would lovingly bake these little delights, waiting anxiously for the return of their husbands from the sea—sadly, a day that for some, would never come. Today, heartbreakingly, the tarts are baked only by widows, perhaps the most sorrowful story behind any dessert I have ever tasted.

Having earlier viewed a fort perched high upon a mountaintop, we were curious to discover the history within its walls. The road was steep, but thankfully, the breathtaking view of the bay and nearby Guadeloupe kept us motivated. We watched with envy as golf carts and scooters zipped past effortlessly. Built on a bluff, the fort was originally named Fort Louis. Destroyed by British forces in 1809 and rebuilt in 1867, the fort was later named after Napoleon and never again used in battle. Instead, it was used as a penitentiary, and is currently a museum open to the public. As we wandered through the gardens surrounding the fort, large iguanas could be seen dozing sleepily on warm rocks, enjoying the sun and posing for the tourists’ photographs. The fort’s fascinating history was detailed within its stone walls, with scale models of English and French ships, along with photographs and maps of the island. These displays provided us with an appreciation of this quaint island’s history, culture and environment.

Gorgeous Saintes Bay looked like the kind of image that would be made into a jigsaw puzzle. With our bird’s-eye view over almost the entire island, it was clear to see why the mountainous dry land did not allow the establishment of agriculture. This, in turn, meant that the island was not settled by slaves, unlike most of its neighbors. Since the island has no source of fresh water, the original settlers were not farmers but rather hearty French fishermen who figured out ways to survive when those before them could not. The arid land below was peppered with clusters of tiny cottages among the scrublike landscape, and for a moment, I forgot I was in the Caribbean. Instead, it felt like I was in the Mediterranean, staring out over a Greek or Croatian island.

Making our way back to the village, we decided to stop at a local creperie for lunch. Savoring jambon, fromage and chocolat crepes, we enjoyed the enchanting French conversations that could be heard floating all around us. The island felt European, and its sleepiness during the heat of the day reminded us even more so of our bygone days backpacking around France, Italy and Greece. The many tourists who had arrived by ferry from neighboring islands that morning had dissipated, and the town was now quiet and peaceful.

Following the meandering road out of town, we decided to visit the most popular beach on the island. Pain de Sucre, named after Sugar Loaf Mountain in Rio De Janeiro, was quite a hike and took an hour by foot. The hills were steep, and the hot sun was burning our already tanned skin. With a view over the bay, we spotted Roam floating peacefully below. Snapping a quick photo, we laughed at the fact that a sailor never tires of admiring their boat. The road followed the shoreline, and the red roofs gave way to sapphire-blue water. Goats wandered freely, grazing on the dry grass, and birds could be seen riding thermal currents at eye level.

The miniature beach, found at the bottom of a craggy rock trail, was picture-perfect, and we were desperate to submerge our bodies in the turquoise water. Protected by rocky cliffs on either side, the small bay was lined with coconut palms and fine white sand. Like a scene from a postcard, couples snorkeled in the shallows, likely on their honeymoon. Soaking in the tranquility of the secluded beach, it was tempting to linger; however, the sun was low in the sky, and the day was drawing to an end.

Too exhausted to make the return trek and knowing we wouldn’t arrive before dark, we stuck out our thumbs for a ride. The very first vehicle to approach us stopped. With a quick bonjour, we scrambled into the minivan and wound our way back through the countryside. With a distinct coastal vibe, the town’s main road now bustled with tourists, and the smell of tantalizing seafood filled the air. Spotting a churros vendor, a meager 2 euros had us licking icing sugar from our lips. A sweet ending to a delightful day.

I stole one last view of the harbor as we dinghied back to our boat. Reveling in its beauty and feeling relaxed and content, I wanted to capture the moment on film. The view was even more beautiful than I remembered that morning, yet the lens did not do it justice. With a golden hue now cast over the bay, the water was glistening in the low light, an image I would just have to burn into my memory. A beautiful white boutique hotel sat to the left, and I dreamed of a night between its crisp white sheets. For now, though, I would have to be content with my boat, and I desperately hoped the swell had abated. Typical of the cruising lifestyle, we had experienced both highs and lows in one day. Au revoir, Terre-de-Haut. You were undeniably one of the most charming and idyllic islands we have visited on our journey so far, and one of the Caribbean’s best-kept secrets. Shh, don’t tell anyone!

Hailing from the land Down Under, Erin and her family quit the rat race and moved aboard a vessel they had bought, sight unseen, on the opposite side of the world. Two years earlier, they had come up with the crazy idea after watching a documentary. Roam, their Moody 47, ­became their ticket to freedom, and carried them safely around the Eastern Caribbean and across the Atlantic Ocean to the Azores, where she sits today, patiently waiting for her next adventure. Follow Erin’s journey on Facebook and Instagram.

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