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Navigating the lush coastlines of tropical islands is the dream of any sailor. But where are the best places to go sailing in the Caribbean?

Whether you’re looking for a romantic sunset catamaran trip or the thrills of racing a sleek America’s Cup yacht, you’ll find your sailing dream in the Caribbean.

Puerto Rico

Isla Verde, one of the best sailing in the Caribbean

Isla Verde, Puerto Rico

Thanks to a 300-mile coastline, sailing is a great way to explore Puerto Rico’s spectacular beaches. Winds that average ten to 15 knots throughout the year make it a pleasurable experience, no matter what your skill level.

Between San Juan and Fajardo, only an hour away, you have a choice of ten marinas. You can rent a boat or catamaran and a crew if need be.

Sailing excursions are a gentle way to explore the coast and have some of the best views of the island’s historic sights. Among the most impressive of these are the 16th-century forts of San Juan Bay, set up to defend the harbor.

Aerial view of Culebra in Puerto Rico

Culebra, Puerto Rico

Nearby islands such as Culebra and Vieques offer unspoiled coral reefs and rich marine life. When sailing, you have a much quieter interaction with any dolphins or sea turtles that might play around the boat.

Sailing slows life down to “island time”, putting you more in touch with the natural world. Add in onboard drinks and snacks, and life becomes even more relaxed.

Grand Cayman

Family sailing in Grand Cayman

Grand Cayman

Renowned among divers for its crystal clear water and healthy coral reefs, Grand Cayman also makes a great sailing destination. The mild tropical weather and steady eastern trade winds are the perfect combination.

The North Sound is a vast sheltered bay, protected by a barrier reef, that is perfect for dinghy sailing. It’s home to the Grand Cayman Yacht Club and various charter companies.

Aerial view of Stingray City, Grand Cayman

Stingray City, Grand Cayman

You’ll also find the famous Stingray City here, where you can moor up to swim among rays. The beaches at Rum Point, Starfish Point, and Kaibo are also excellent.

Aside from being one of the best beaches in Grand Cayman, Seven Mile Beach is a popular destination for more experienced sailors. With only two docks, it’s usual to just anchor offshore from one of the many good restaurants.

St. Lucia

Pretty landscape of St. Lucia

St. Lucia

It may be true of any island, but the best view of Saint Lucia is undoubtedly from the sea. The glorious green slopes of the Pitons stand out best when seen against the bright tropical blue water.

There are several sailing charter companies on the islands. It’s a great place to learn to sail, improve your skills, or just relax with an experienced skipper, listening to music, rum punch in hand as you take in the glorious coastline while someone else does the work.

With St. Lucia’s beautiful beaches, lush tropical shores, and lively towns, this island jewel has many facets. The calm Caribbean caresses its western shore, while the wilder Atlantic hits the eastern one.

St Lucia, one of the best places for sailing in the Caribbean

St. Lucia

Its coastline has countless picturesque bays and coves to anchor in. The largest marina is Rodney Bay, while Marigot Bay and Soufrière also supply good moorings. Often, you can jump right off the boat into the warm Caribbean in these spots.

St. Thomas

Catamaran in St. Thomas

St. Thomas

As part of the U.S. Virgin Islands, St. Thomas has become a major sailing destination. Experienced crews and excellent facilities let you explore the natural beauty of the Virgin Islands with confidence.

Sailing and snorkeling tours are a good choice for many visitors. Experienced skippers and guides take you to the best places to sample the underwater life in several different islands.

Woman snorkeling in The Baths at Virgin Gorda

The Baths of Virgin Gorda

Popular sites include Virgin Gorda in the British Virgin Islands, famous for its rock pools at The Baths, and Norman Island, reputed inspiration for Stevenson’s “Treasure Island”.

Jost Van Dyke, also in the British Virgin Islands, means calling into Foxy’s Bar for a calypso break. Sail-filled White Bay here is an almost perfect curve of white sand, palm trees, and green hills.

Aerial view of Charlotte Amalie, St. Thomas

Charlotte Amalie, St. Thomas

Back in the capital of the U.S. Virgin Islands, Charlotte Amalie, you can find historic sites, sunset waterfront dining, and duty-free shopping in St. Thomas. Don’t miss the copy of the Liberty Bell in Emancipation Garden.

St. Croix

View of St. Croix from the water

St. Croix

While also part of the U.S. Virgin Islands, St. Croix differs from St. Thomas in being further south. The island’s many beautiful, sheltered anchorages and sights such as Buck Island, mean you’re not missing out.

St Croix, one of the best places for sailing in the Caribbean

Buck Island National Reef Monument

Buck Island National Reef Monument, just off the northeast coast, is a must-visit, and all the better by boat. This protected marine park has healthy Caribbean coral reefs that you can explore on an underwater snorkel trail.

Salt River Bay preserves the Columbus Landing Site, where the Spanish explorer first set foot on what is now U.S. soil. It’s a beautiful area of mangrove forests, with a bioluminescent bay.

Waterfront view of Christiansted, St. Croix

Christiansted, St. Croix

Christiansted, the main town of St. Croix, is notable for its Danish architecture and lovely harbor. Frederiksted has Victorian architecture and a pier where every second person seems to be a sailor.

St. Kitts

Lush landscape of St. Kitts

St. Kitts

St. Kitts and its sister island of Nevis, are a great mix for sailors of warm waters, gentle trade winds, and natural beauty. Basseterre, the capital, has a busy harbor, while Christophe offers another modern marina in the island’s southeast.

Catamaran tours offer full-day, half-day or sunset cruises to explore both islands. These supply refreshments and snorkeling gear, so you can enjoy life both above, and under the water.

Man sailing in St. Kitts

St. Kitts

Sitting where the Caribbean meets the western Atlantic, St. Kitts has a lovely mix of conditions. It’s increasingly popular for ocean racing, while still being suitable for novice sailors.

The Great Salt Pond is a good mooring on the southeast coast, from where you can go kayaking or bird-watching. A more lively atmosphere is found at Friars Bay, where bars and restaurants contrast to the idyllic swimming and snorkeling.

St. Maarten

St Maarten, one of the best places for sailing in the Caribbean

St. Maarten

The tiny island of St. Maarten/St Martin is shared between two countries, the Netherlands and France. Sailing around it allows you to sample both cultures, enjoying their different cuisine and shopping.

There is also the natural beauty of St. Maarten’s beaches, reefs, and remote islets. Steady easterly trade winds and a sheltered setting make it a sailor’s paradise as well.

Sail excursions allow you to see the mountainous coastline, and lush interior from a picturesque distance. Then you can snorkel in a quiet cove, or just swim amid the awesome natural beauty.

Beautiful white sands of Grand Case Beach

Grand Case Beach, St. Maarten

Any sailor will also want to experience being on an America’s Cup racing yacht. Several former winners or contenders offer you a thrilling time aboard these race cars of the sea.


Boat sailing in Bonaire


Bonaire puts the “B” in the Dutch “ABC Islands”, the others being Aruba and Curaçao. Outside the hurricane belt, they make for a great sailing destination.

Kralendijk, Bonaire’s capital, is also the main port. The palm-lined waterfront is a colorful setting for good restaurants, shops, and markets.

Noted for its diving and snorkeling, the entire coast of Bonaire is a protected national park. Sailing excursions will take you to perfect beaches, and offer guided snorkeling tours to learn more.

Couple walking along Bonaire waterfront


One of the best things to do in Bonaire is to visit Lac Bay, on the island’s eastern side, which has become a hot spot for windsurfing, kitesurfing, and sailing. Its shallow, remarkably clear water makes it ideal for novice and experienced sailors.

Flamingos in Lac Bay, Bonaire

Flamingos in Lac Bay, Bonaire

The island’s salt pans are also home to flocks of flamingos. After watching them fly into the air, you can share the experience by diving into seawater that is clear to 100 feet.

Other popular excursions include evening champagne cruises to enjoy the amazing colors of the Caribbean sunset. Who can ever resist the urge to photograph this most powerful of vacation memories?

Read: Best Places to Go Diving in Bonaire


Grenada, one of the best places for sailing in the Caribbean

St. George’s, Grenada

St. George’s is said to be the prettiest town in the Caribbean. That’s only one of the charms that put Grenada among the best places to go sailing in the Caribbean

One of the smallest independent countries in the Caribbean, Grenada is the most southern of the Windward Islands. It’s famous as the “Spice Island” for its production of cinnamon, cloves, ginger, and other fragrant delights.

Old-time sailors said they could smell the island from miles away. You can put that to the test by sailing the shore, enjoying sights such as Levera Beach and nearby Sugar Loaf Island.

Sandy beach of Levera Beach, Grenada

Levera Beach, Grenada

One of Grenada’s best beaches, Levera Beach is home to nesting turtles, and this secluded stretch of sand has great views to the north. That view includes the peak of Sugar Loaf, and might tempt you to explore the Grenadines.

Divers won’t want to miss seeing the Grenada Underwater Sculpture Park. These mesmerizing underwater sculptures make up an artificial reef that attracts plentiful marine life.


Belize, one of the best places for sailing in the Caribbean


With the world’s second-largest coral reef off its coast, and untouched rainforest behind, Belize is a natural paradise. Sailors can enjoy the best of both worlds, along with carefree sailing in perfect conditions.

Divers already know about the Great Blue Hole, made famous by Jacques Cousteau, and one of the world’s best dive sites. It’s off Lighthouse Reef, an atoll that’s part of the Unesco-protected Belize Barrier Reef Reserve System (BBRRS).

Marine life in Belize Barrier Reef Reserve System

Belize Barrier Reef

The reef gives protected sailing inside it, and also provides idyllic viewing for divers and snorkelers. You’ll find some of the best-preserved coral in the world here.

The water here is dotted with countless small islands (cayes), where you can find your own temporary slice of paradise. Larger islands include Ambergris Caye, where sailors gather to stop stories and enjoy great dining.

Fisherfolk will enjoy Whipray Caye, both for the fishing and the food afterward. South Water Caye is a place to swim, sunbathe, and enjoy more great diving and snorkeling in Belize.


White sand beach of Antigua


Antigua is practically synonymous with sailing in the Caribbean. Favorable trade winds, superb anchorages, and a strong sailing community have put it on everyone’s nautical chart—not least during the annual Antigua Sailing Week.

The Eastern Caribbean island has a long, varied coastline, with prevailing easterly winds. That means sailors of any ability will find conditions to suit, from long ocean stretches to sheltered coves.

Aerial view of Nelson's Dockyard, Antigua

Nelson’s Dockyard, Antigua

English Harbour, on the southeastern coast, is the site of Nelson’s Dockyard, a Unesco World Heritage Site. One of the world’s best-preserved Georgian naval dockyards is only 40 minutes from the capital, St. John’s.

As you explore the coastline, you’ll find many smaller islands offshore, home to some of the best snorkeling in Antigua. These include Green Island, a common overnight anchorage, and Great Bird Island, which has hiking trails, and plentiful marine life.

Further away is the island of Barbuda, which makes a great open-water crossing. It’s known for its pink sands and the rich birdlife of the Frigate Bird Sanctuary.

Boat in Antigua


Has this list of the best places to go sailing in the Caribbean inspired your nautical side? Then why not browse our Caribbean cruises to find the perfect voyage for you and your loved ones?

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