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The most beautiful sailing destinations in the Caribbean

– 19 October 2023 – Sailing itineraries

Sailing itineraries

The most beautiful sailing destinations in the Caribbean

The Caribbean has always been one of the most beautiful and favorable seas for sailing, with countless breathtaking islands waiting to be explored. Among the most favored destinations for sailors in the Caribbean Sea are the Cayman Islands, the US Virgin Islands, Saint Lucia, the British Virgin Islands, Guadeloupe, the Grenadine Islands, Grenada, St. Vincent, and Antigua. A significant part of their allure undoubtedly comes from the natural beauty these islands offer, including crystal-clear waters, tropical beaches, and some of the most stunning coral reefs in the world. However, much of their appeal also stems from their rich history, sailing infrastructure, and the numerous attractions available for sailors.

There’s also the incredibly favorable climate, especially when it’s winter in the Mediterranean. Sailing in the Caribbean promises warm weather and magnificent waters, warm enough to swim in year-round. Hurricane season can pose a challenge. However, the threat is mitigated thanks to modern weather technology and careful planning by cruising sailors. So, here are the best and most beautiful sailing destinations in the Caribbean, along with some of the top attractions to visit.

Also read: Croatia: Top 7 amazing stopovers you shouldn’t miss on a sailing cruise

Antigua, a true “mecca” for exotic sailing leisure

Antigua is a flower-shaped Caribbean island known for its unique wildlife and pristine beaches. The island, which remained largely isolated for centuries, is home to some of the world’s rarest creatures, such as the Antiguan racer snake and Griswold’s Ameiva lizard. Antigua showcases the climate and landscape the Caribbean has to offer. It’s a popular destination for sailing and boating, with facilities on the island dedicated to sailing vessels and assisting boat owners with all their travel paperwork.

Antigua also hosts a massive regatta that draws hundreds of swift sailing boats every year. The Antigua Sailing Week is a globally renowned event, both delightful to participate in and watch. Throughout the rest of the year, the island shelters hundreds of boats in its many bays and protected coves.


Saint Lucia, perfect for taking photos from the boat

Saint Lucia is a Caribbean gem known for its excellent sailing conditions and its majestic mountainous islands. The island also boasts luxury resorts and top-notch amenities, as well as sheltered anchorages for sailboats and yachts. While the island’s official language is French, most people speak English. The beaches rank among the best in the world, and the landscape is lush with tropical plants, vibrant flowers, and diverse wildlife.

Like most Caribbean destinations, the waters around the island have shallow spots, making them ideal for diving and snorkeling. Saint Lucia is also an excellent destination for photography due to its unique and iconic rock formations.

Cayman Islands, modern with ample nautical services

The Cayman Islands were likely discovered by Christopher Columbus in 1503. This once uninhabited island archipelago, located south of Cuba, offers spectacular sailing. The islands consist of Little Cayman, Cayman Brac, and Grand Cayman, which is the largest. Today, the Cayman Islands are part of the British Commonwealth, with a population of around 71,000 residents. They feature modern, welcoming anchorages, and a coastline that alternates between rocky stretches and outstanding beaches and marinas. The climate is warm and tropical, and the islands are not far from the continental United States. Everyone speaks English, making it easy to arrange excursions and socialize.

The Cayman Islands boast various marinas, rental services, and even a sailing club. The clear, shallow waters surrounding the islands offer fantastic diving and snorkeling opportunities. The local climate is almost always warm and favorable. However, one must be cautious of hurricanes, which occasionally pass through during the summer months.


U.S. Virgin Islands, beginner-friendly sailing

The U.S. Virgin Islands are a U.S. territory, home to an official population of around 100,000 people. They offer a sailing destination that’s easily navigable even for less experienced sailors. This small chain of tropical Caribbean islands uses the U.S. dollar as its primary currency, and English is the official language. Spanning a total area of about 133 square miles, they rank among the smaller destinations on our list. These islands are directly adjacent to the British Virgin Islands, another top sailing destination.

The shallow waters along the coast make the U.S. Virgin Islands an excellent spot for diving, and the region teems with marine life. Surrounding the main islands are dozens of smaller isles offering the chance to explore secluded natural destinations.

Grenada and St. Vincent, the soul of the Tropics

Grenada, a region encompassing numerous islands including the Grenadines, also features St. Vincent. This volcanic island is lush green and renowned for its natural beauty. The capital, Kingstown, offers various gathering spots like bars and restaurants and is just one of many seaside towns to explore.

One of the island’s most popular tourist destinations is the St. Vincent Botanical Gardens. Under continuous conservation efforts, the area showcases a plethora of tropical plants and animals, along with vibrantly colored and rare island birds.

British Virgin Islands, where sailing reigns supreme

British Virgin Islands, where sailing reigns supreme. The British Virgin Islands are situated right next to the U.S. Virgin Islands and provide some of the same stellar sailing opportunities. This chain of islands is home to about 30,000 people. Sailing is an integral part of local life and is the only way to reach many of the most sought-after spots. These petite islands still belong to the UK’s commonwealth, and English is the official language. The islands host an annual regatta, a great way to mingle with crews from all over the world.

The British Virgin Islands deliver a splendid tropical backdrop, but also feature numerous coral reefs and rock formations to explore. For instance, the Baths on Virgin Gorda are a mystical and popular natural wonder to explore on the islands.


Guadeloupe, a sea surrounded by greenery

Nestled within the Les Saintes archipelago, Guadeloupe stands out as an excellent sailing destination, offering nautical services and beautiful anchorages. The island appeals particularly to seasoned sailors and offers numerous opportunities for socializing without the crowding of more tourist-heavy islands. Guadeloupe, a French territory, is adorned with lush forests and a stunning coastline waiting to be explored. The main island is nearly covered in green, presenting a rare and largely untouched view of tropical natural life. Basse-Terre, its largest city, is home to the majority of the island’s 395,000 residents.

rench is the island’s official language, though many speak English, and it boasts immigration and customs facilities. Furthermore, being under French administration, the island is a member of the European Union and accepts the euro. It’s worth noting that on older maps, the regions of Saint Barthelemy and Saint Martin might be included under Guadeloupe, but these regions underwent a referendum and separated in 2003. Nonetheless, these nearby destinations offer stellar sailing and exploration opportunities.


Grenadine Islands, a sailing paradise

The Grenadines are recognized worldwide as a premier sailing destination, with various small islands forming the larger chain. These islands are famed for their tropical allure and the solitude they offer, making them an idyllic destination for serene family cruises in the Tropics. Many of the Grenadine islands were once privately owned, but are now uninhabited, showcasing breathtaking landscapes.

The rocky Grenadine islands also boast numerous coral reefs, with plenty of anchorages to unwind, snorkel, and partake in water sports like kitesurfing and windsurfing. Carriacou Island houses most of the population and offers several amenities to sailing vessels and other boats.

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