Island Hopping the Windward Islands by Sailboat

In a Nutshell...

Island hopping through the Windward Islands by sailboat is a fantastic adventure that takes you on a chain of scenic, diverse islands, from the French-influenced Martinique to the spice capital of Grenada. The journey offers a mix of secluded anchorages, vibrant port towns, and stunning natural beauty. This guide provides an experienced sailor’s take on the best anchorages, local customs, and key navigational tips to help you get the most out of your Windward Islands sailing adventure.

Sailing the Windward Islands: A Southern Adventure

Having wrapped up our journey through the Leeward Islands, our compass is now set firmly south towards the Windward Islands. If the Eastern Caribbean is a cruiser’s paradise, then this chain of islands is surely its sparkling centrepiece. This stretch includes four primary nations: Martinique, St Lucia, St Vincent & the Grenadines, and Grenada. While each island is a unique world, they all share that irresistible Caribbean charm.

Before we set off from Dominica, the southernmost point of the Leeward chain, we made sure to have our up-to-date navigational charts and pilot books ready. A well-planned passage is a happy passage, and the route to Martinique is a great way to start this new leg of our voyage.

Martinique: A Touch of France in the Tropics

Martinique is the first stop in the Windwards, and as a full-fledged part of the French Republic, it feels distinctly different from the islands to the north. Sailing into a place where you can pick up a baguette for breakfast and find comprehensive yacht services is a real treat. The west coast is a treasure trove of anchorages.

• Ports of Entry: St Pierre, Fort de France, Marin, Anse Mitan, Grand Anse d'Arlet, St Anne

• Currency: Euro (€)

• Official Language: French

Sailing down from Dominica, the first spot you'll likely hit is St Pierre, a town that sits in the shadow of the infamous Mont Pellée, the volcano that erupted so tragically in 1902. While anchoring here can be a bit challenging due to the quick drop-off, the town itself is a bustling fishing village with excellent restaurants.

Further south, you’ll find other great stops. Fort de France is a major hub, and if you’re looking for a quiet spot, the sheltered waters of Les Trois Ilets are a great choice. As a sailor who has spent a lot of time on these waters, I can tell you that the string of anchorages south of Baie de Fort de France—like Anse Mitan and Grande Anse d'Arlet—are perfect for leisurely cruising.

Marin is where you’ll find full yacht services, including marinas, boatyards, and chandleries. It's also one of the key places to check out before you make what is typically a fast, exhilarating reach over to St Lucia.

St Lucia: The Pitons & a Pirate's Past

St Lucia is a sailor’s favourite for good reason. If you arrive at Rodney Bay in mid-December, be prepared for a crowd. It’s the finish line for the ARC (Atlantic Rally for Cruisers), so the bay and marina are packed with boats and weary crews.

• Ports of Entry:Rodney Bay, Castries, Soufriere, Vieux Fort

• Currency:Eastern Caribbean Dollars (EC$)

• Official Language: English

Many cruisers check in at Rodney Bay before heading south. A must-see on the way is Marigot Bay, famous for being a filming location for Dr Dolittle. Just a short sail further south, the majestic volcanic plugs of the Pitons dominate the skyline. Anchoring or picking up a mooring here at Soufriere is an unforgettable experience.

From Soufriere, you can check out or continue to Vieux Fort at the southern tip of the island. Next up is St Vincent, where a lively acceleration zone off the northern end of the island can provide a memorable, and sometimes thrilling, passage.

St Vincent: Volcanic Shores & Film Sets

St Vincent’s rugged, volcanic landscape has seen its share of drama, both natural and man-made. The 2021 eruption of the La Soufrière volcano brought an end to many of the hillside plantations and caused massive disruption with its ash cloud.

• Ports of Entry: Chateaubelair, Wallilabou, Kingstown

• Currency: Eastern Caribbean Dollars (EC$)

• Official Language: English

Arriving from the north, you can check in at Chateaubelair. Just a few miles further south, Cumberland Bay offers a unique anchoring experience. The water is so deep that you drop your main anchor off the shelf and use a long line ashore, often with the help of a friendly local boat boy, to tie off to a palm tree. This "stern-to" approach is common here and at Wallilabou, famous for being a location for the Pirates of the Caribbean films. It’s an unusual but effective way to moor.

Other spots like Barrouallie, Buccament Bay, and Petit Byahaut dot the coast. Blue Lagoon is a well-protected, comfortable anchorage, but its entrance is a bit of a tight squeeze. Once you’re done exploring St Vincent, the delightful Grenadines await.

The Grenadines: Turquoise Waters & Island Charms

The Grenadines are a string of 32 islands and cays that form part of the nation of St Vincent & the Grenadines. They are a cruiser's dream with stunning turquoise waters and vibrant marine life.

Bequia

Just a 10-mile sail from St Vincent, Bequia is a popular cruising hub. Admiralty Bay in Port Elizabeth is a fantastic place to anchor, with plenty of shops, bars, and restaurants ashore. My own experiences there have always been lively and welcoming.

Mustique

Mustique is a privately-owned island that has become a playground for the rich and famous. While you can only anchor in Britannia Bay and are expected to pick up a mooring if one is available, it’s worth a visit. Our friends once had a beer at the legendary Basil's Bar and were joined by Mick Jagger for a jam session—we sadly arrived a day too late!

Canouan

Canouan has transformed from a quiet island into a high-end resort destination. With a new jetport and marina, it's known as "the place where billionaires go to escape millionaires." Thankfully, there are still quiet anchorages like L'ance Guyac Bay and Rameau Bay where regular sailors can find peace.

Mayreau & The Tobago Cays

The Southern Grenadines are where you can truly relax and enjoy the pristine nature of the islands. Mayreau is a part of the Tobago Cays Marine Park. The popular Saltwhistle Bay is a must-see, although it can get crowded. The nearby Saline Bay is a great alternative. From there, you can easily walk the island's tracks for a scenic circumnavigation.

The Tobago Cays themselves are simply breathtaking. The five uninhabited islands—Petit Rameau, Petit Bateau, Baradel, Jamesby, and Petit Tabac—are enclosed by the Horseshoe Reef. The marine life here is astounding; you can see turtles and rays from your cockpit. It's a national park and an experience not to be missed.

Union Island

Union Island is the southernmost of St Vincent & the Grenadines. Chatham Bay is a great anchorage, but be aware of the sudden, strong katabatic winds that roll down the mountains. A short dinghy ride will take you to the village of Ashton. My wife Mary once nearly got knocked out of our dinghy by a pelican there—a memory that always brings a smile to my face. From Clifton Harbour on Union Island, you’ll check out and prepare for the final leg of our journey to Grenada.

Carriacou: Boatbuilding & Hurricane Holes

Carriacou is administratively part of Grenada and is famous for its traditional wooden boatbuilding. You can easily get around on the local buses to explore the island and visit the village of Windward. The main port of entry is now at Tyrrel Bay. It’s a hugely popular anchorage with two boatyards, a chandlery, a supermarket, and a great mangrove lagoon that serves as a well-known hurricane hole.

Grenada: The Spice Isle

The final destination on our Windward Islands sailing adventure is Grenada, a beautiful island known as the "Spice Isle." But first, a word of caution: you must navigate around Kick 'em Jenny, an active underwater volcano between Carriacou and Grenada. Always check the official marine advisory before you make this passage.

• Ports of Entry:St Georges, Prickly Bay, St Davids Harbour

• Currency:Eastern Caribbean Dollars (EC$)

• Official Language:English

Grenada’s south coast is dotted with sheltered, indented bays. Prickly Bay is a favourite for many cruisers, offering a well-stocked boatyard and a marina. Hog Island is a particularly popular spot for liveaboards, providing excellent protection. The Dodgy Dock Bar at True Blue Bay is also a personal favourite and a great spot for a rum punch.

Other anchorages include True Blue Bay, Mount Harman Bay, Hog Island, Clarkes Court Bay, and St Davids Harbour—all offering secure havens with great facilities. Grenada is also a major hub for hurricane season, with plenty of options for storage ashore.

The above sketch-maps of the islands are reproduced here with the kind permission of their creators, 'Superyacht Publications Ltd', and are taken from their super-useful Superyacht Services Guides for the Caribbean in which they make recommendations for all yachting services in each of the islands.

Provisioning & Local Markets

A successful cruise isn't just about sailing; it's also about eating well. While you can find supermarkets on most of the larger islands, some of the best culinary experiences come from local markets. On Grenada, for instance, the St George’s market is a fantastic place to buy fresh spices, fruit, and vegetables. In Bequia, Port Elizabeth has great local stalls for stocking up on supplies. Don't be shy; haggling is a part of the fun and a great way to engage with the community. Remember that some smaller islands, like the Tobago Cays, have no shops, so you'll need to provision thoroughly beforehand.

Safety & Security

While the Caribbean is a welcoming place, a seasoned sailor knows that safety is paramount. When anchored, make sure your boat is secure and that all hatches are locked, particularly at night or when you go ashore. Be aware of your surroundings and trust your instincts. The islands are also a part of a major hurricane zone, so if you're sailing during the off-season (June to November), have a detailed hurricane plan. Grenada, in particular, offers excellent hurricane holes and boatyards for storage. For more in-depth advice on preparing your vessel for a long voyage, check out our comprehensive guide on Sailing in the Caribbean: Information for Skippers & Crew.

Cultural & Environmental Etiquette

As visitors, we have a responsibility to respect the local environment and culture. When on land, a simple "Good morning" or "Good afternoon" goes a long way. The locals are incredibly friendly, and taking the time to chat can provide great insights into the islands. From an environmental perspective, please use designated bins for waste and avoid dumping rubbish overboard. Also, take care when anchoring to avoid damaging coral reefs, especially in marine parks like the Tobago Cays. Many protected areas have moorings for this very purpose.

Customs & Local Regulations

Navigating the bureaucratic side of sailing is a necessary part of the adventure. Each country in the Windward Islands has its own unique set of regulations, and they are best handled with patience and a smile. Remember to have your boat's papers, passports, and crew list ready for inspection. The process of clearing in and out of a port of entry can sometimes take a while, so plan your day accordingly. In St Vincent & the Grenadines, you only need to clear into the nation once, typically in Bequia or St Vincent. However, when leaving the country, you must check out.

Tours & Shore Excursions

Don't spend all your time on the water! The Windward Islands offer incredible experiences ashore. In St Lucia, you can visit the Sulphur Springs, the Caribbean's only drive-in volcano. On Grenada, a trip to a nutmeg factory is a fascinating experience, and the spice plantations are truly a feast for the senses. Hiking up one of the Pitons in St Lucia or exploring the remote waterfalls on St Vincent are also highly recommended.

Summing Up

Sailing the Windward Islands is more than just a passage; it’s an immersive journey that connects you with the heart of the Caribbean. Each island has its own unique flavour, from the French flair of Martinique to the historic shores of St Vincent and the natural wonders of the Grenadines. Finally, arriving in Grenada, you'll have reached a vibrant and well-equipped hub that perfectly concludes the adventure. It’s a trip that stays with you long after the anchor is up.

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