Sailing the Caribbean: Best Islands to Visit
Sailing the Caribbean: Best Islands to Visit

Explore the best islands to visit in the Caribbean and plan your next sailing adventure with your family. Discover unique destinations, stunning natural beauty, and a laid-back atmosphere that will inspire and excite you.

Sailing the Caribbean: Best Islands to Visit

The Caribbean is a dream destination for many sailors, offering a diverse range of islands, each with its own unique charm and beauty. With crystal-clear waters, white sandy beaches, and a laid-back atmosphere, it’s no wonder that the Caribbean is a popular choice for those looking to escape the rat race and embark on a sailing adventure with their families.

In this article, we’ll explore some of the best islands to visit in the Caribbean, providing you with a comprehensive guide to help you plan your sailing itinerary. Whether you’re a seasoned sailor or a complete novice, these destinations are sure to inspire and excite you as you set sail on your Caribbean adventure.

The British Virgin Islands

The British Virgin Islands (BVI) are a collection of over 60 islands and cays, offering a fantastic mix of secluded anchorages, bustling marinas, and pristine beaches. The BVI is a popular destination for sailors due to its consistent trade winds, line-of-sight navigation, and well-protected harbors.


Tortola is the largest and most populated island in the BVI, and is home to the capital, Road Town. This bustling town offers a range of amenities, including supermarkets, restaurants, and shops, making it a convenient stop for provisioning and exploring the local culture.

Virgin Gorda

Virgin Gorda is known for its stunning natural beauty, with highlights including The Baths, a unique geological formation of granite boulders that create a series of pools and grottos to explore. The island also offers excellent snorkeling and diving opportunities, with numerous coral reefs and shipwrecks to discover.

Jost Van Dyke

Jost Van Dyke is a laid-back island with a vibrant social scene, making it a popular stop for sailors looking to unwind and enjoy some local hospitality. The island is home to the famous Soggy Dollar Bar, where you can sample the original Painkiller cocktail while relaxing on the beautiful White Bay beach.

The Grenadines

The Grenadines are a chain of 32 islands and cays, stretching between the larger islands of St. Vincent and Grenada. This island group offers a more off-the-beaten-path experience, with fewer crowds and a more relaxed pace of life.


Bequia is a charming island with a strong maritime heritage, making it a popular destination for sailors. The island’s main town, Port Elizabeth, offers a range of amenities, including shops, restaurants, and a lively market. Bequia is also home to some beautiful beaches, such as Princess Margaret Beach and Lower Bay.


Mustique is a private island known for its celebrity visitors and luxurious villas. While the island is primarily a playground for the rich and famous, sailors can still enjoy the beautiful beaches and crystal-clear waters by anchoring off the coast and visiting the island’s two public beaches, Macaroni Beach and Lagoon Beach.

Tobago Cays

The Tobago Cays are a group of five uninhabited islands, surrounded by a horseshoe-shaped coral reef. This protected marine park offers some of the best snorkeling and diving in the Caribbean, with an abundance of marine life, including turtles, rays, and colorful fish. The Cays are also a popular spot for kiteboarding, thanks to the consistent trade winds.

St. Martin and St. Maarten

St. Martin is a unique island, divided between French and Dutch territories. This dual nationality gives the island a fascinating blend of cultures, with a range of culinary delights, shopping opportunities, and nightlife options to explore.

Marigot, St. Martin

Marigot is the capital of the French side of the island and offers a taste of European sophistication, with its stylish boutiques, art galleries, and gourmet restaurants. The town is also home to the historic Fort Louis, which offers panoramic views of the surrounding area.

Philipsburg, St. Maarten

Philipsburg is the capital of the Dutch side of the island and is known for its lively atmosphere and duty-free shopping. The town’s waterfront is lined with colorful buildings, housing a range of shops, bars, and restaurants, making it a popular stop for sailors looking to enjoy some onshore entertainment.

Antigua and Barbuda

Antigua and Barbuda are two separate islands, each offering a unique Caribbean experience. With 365 beaches, one for every day of the year, Antigua is a sailor’s paradise, while Barbuda offers a more remote and tranquil escape.

English Harbour, Antigua

English Harbour is a historic naval base, home to the impressive Nelson’s Dockyard, a UNESCO World Heritage site. The harbor offers a range of amenities for sailors, including marinas, restaurants, and shops, as well as the popular Shirley Heights lookout, which offers stunning views of the surrounding area.


Barbuda is a pristine island, known for its pink sand beaches and untouched natural beauty. The island offers a peaceful retreat for sailors looking to escape the crowds and enjoy some solitude. The Frigate Bird Sanctuary is a must-visit for nature lovers, with thousands of frigate birds nesting in the mangroves.


The Caribbean offers a diverse range of islands to explore, each with its own unique charm and attractions. From the bustling towns of St. Martin and Tortola to the tranquil beauty of Barbuda and the Tobago Cays, there’s something for every sailor to enjoy.

As you plan your Caribbean sailing adventure, be sure to consider the destinations outlined in this article, and remember to embrace the freedom and fulfillment that comes from choosing an unconventional path and exploring the open sea with your family.