Caribbean Cruising: The Top 8 Islands for a Yacht Vacation 

The Caribbean continues to top the list for luxury yacht vacations, thanks to its pristine beaches, lively culture, abundant marine life, and island-to-island proximity that makes multi-stop itineraries effortless.

Thanks to the steady trade winds and reliable cruising conditions during the peak season, the best time to cruise here is from December through April.  An island-hopping destination that’s ideal for both first-time yacht charterers and seasoned guests, there is something to suit every pace and preference.

Here are eight standout Caribbean destinations to consider for your next yacht vacation: 

Antigua

Antigua has long been a favourite among sailors. Located in the Leeward Islands, it has natural harbours and a beach for every day of the year, making it an excellent yachting base. Falmouth Harbour offers premier marinas and easy access to the historic Nelson’s Dockyard, a UNESCO-listed site filled with galleries, restaurants, and restored Georgian architecture. 

Anchor off Galleon Beach for snorkeling and turtle sightings, explore protected anchorages like Nonsuch Bay, or kitesurf off Jabberwock Beach. Dining ranges from casual rotis at Roti Sue’s on Dockyard Drive to leisurely fine dining lunches on Pigeon Point Beach at Catherine’s Cafe. A perfect spot for sundowners is the iconic Jacqui O’s or the cliffside Sheer Rocks, both of which also offer excellent dining options. On Sunday, join locals and visitors for the sunset party at the 17th-century lookout—Shirley Heights—for panoramic views, rum punch, barbecues, and live music. 

Antigua is an ideal launchpad for wider Eastern Caribbean itineraries and a jumping-off point to its smaller sibling, Barbuda, known for its 17-mile pink-sand beach and bird sanctuary. If timed right, you can also catch the Sailing Week or the Antigua Yacht Charter Show.

St. Martin

Split between the French north and Dutch south, with no visible border, this 37-square-mile island offers an intriguing blend of European chic and Caribbean atmosphere. On the Dutch side, St. Maarten is full of nightlife and beach bars around the sheltered Simpson Bay Lagoon. And, in contrast, the French side, St. Martin is more relaxed, offering gourmet dining and a Riviera-style charm. 

Visit Marigot’s colourful markets, stroll through colonial Philipsburg, and anchor off Tintamarre and Ile Pinel, which offer some of the most peaceful beach days. For those seeking watersports, head to Orient Bay to try your hand at windsurfing. And, don’t miss Maho Beach for the surreal sight of planes landing overhead. While the island itself is more than just a stopover, its central location makes St. Martin ideal for itineraries onwards to St. Barts, Anguilla, and Antigua. Conveniently located, the small, volcanic island of Saba (with excellent scuba diving opportunities) should also be added to a St. Martin yacht itinerary. 

St. Barths  

St. Barth’s always makes the must-see Caribbean island lists, and for good reason. Although physically small, it has made a significant impact on the yachting community and is one of the most sought-after destinations. Famous for its end-of-year celebrations and the renowned St Barths Bucket regatta at the end of the high season, St Barths is the place to see and be seen. 

The main port and where yachts flock to anchor, Gustavia, is full of fine dining restaurants, upscale boutiques, galleries, and designer shopping. Aside from the glitz and glamour, the island is full of natural beauty to enjoy. Spend your days anchored off one of the many pristine beaches, such as Colombier Beach, and enjoy extended lunches at lively beach clubs, like Shellona. 

To ramp up the pace, there are endless bays to enjoy a range of watersports, and ashore, you can explore hiking trails. Thanks to the island’s proximity to Anguilla and St. Martin, it is in the perfect location for a wider Caribbean itinerary. 

British Virgin Islands (BVI’s)

A cluster of over 60 islands and cays, the British Virgin Islands (BVIs) offer some of the best island-hopping throughout the Caribbean, with relatively short distances between anchorages, calm trade winds, and crystal-clear waters. 

Highlights of visiting the islands include the famous Baths on Virgin Gorda, an intriguing landscape of giant granite boulders, hidden pools, and grottos that are perfect for swimming and exploring. The North Sound is a well-established yachting haven with protected waters and outposts such as the Bitter End Yacht Club. 

You can fill an itinerary full of underwater spots. There are plenty of options for snorkelling and diving, from exploring sites such as the Indians or the popular RMS Rhone wreck. While ashore, you head to the hiking trails like those found on Guana Island and the quirky island of Buck Island with its resident animals. Extending a cruising itinerary here can be done with a short cruise to the neighbouring islands of the US Virgin Islands (USVI). 

The Bahamas 

Though technically in the Atlantic, the Bahamas are still considered part of the Caribbean for a yachting itinerary. With over 700 islands and cays on offer, the archipelago, split between the Exumas and Abacos groups—just a short trip from Florida—provides endless yachting opportunities. Known for their island-hopping adventures, the islands are a paradise of white sandy beaches, calm trade winds, and clear, shallow waters. 

Visit unique attractions like the swimming pigs of Big Major Cay, dive the blue holes of Long Island, experience shark diving at Tiger Beach, or snorkel coral reefs off Andros. For luxury experiences, visit Paradise Island’s restaurants and championship golf courses. Or unwind on the postcard-perfect pink sands of Harbour Island and Elthuera. The Exuma Cays Land and Sea Park is worth spending a few days enjoying the isolated anchorages and marine life. 

St Vincent & The Grenadines

Another location with more than just one island to explore is St Vincent and the Grenadines. Frequently referred to as the ‘true Caribbean,’ this 30-island chain in the Windward Islands is ideal for one-way cruising itineraries. Begin in St Vincent and explore the lush rainforests and active La Soufriere volcano before sailing south to Bequia, Mustique, Canouan, and Union Island. 

Each offering a unique charm, featuring world-class diving and watersports, secluded beaches, and a vibrant local culture, with festivities and hiking opportunities ashore. A standout highlight is the farthest south at Tobago Cays, a marine reserve where turtles congregate, and you can sip on rum punch sundowners in peaceful anchorages. 

Grenada 

At the southern end of the Windward Islands, and a short hop from Tobago Cays, is Grenada. Widely known as the Spice Island, Grenada offers a more off-the-beaten-track yachting vacation that can be equal parts relaxing and active. 

Begin your yacht vacation in St George’s, explore the island’s picturesque colonial town, and enjoy the upgraded modern Port Louis Marina, full of high-end facilities, from bars and restaurants to duty-free shopping. 

Grenada is best explored through chocolate tastings, spice tours, and authentic dining experiences, such as at Dexter’s, a family-run restaurant serving a seasonal menu. Off Dragon Bay, snorkel or dive the Molinere Underwater Sculpture Park, the first of its kind. While inland, the island is filled with monkeys, waterfalls, and hiking trails in the Grand Etang National Park. 

Martinique 

The French overseas territory of Martinique combines the luxuries of Europe, such as excellent cuisine, chic boutiques, and charming café culture, with the natural allure of tropical landscapes and secluded beaches. 

A perfect location for those seeking active pursuits, the island’s mountainous landscapes give rise to numerous rewarding hikes through rainforest-covered hills and up to Mount Pelee, a still-active volcano. 

Around Saint-Pierre, there are lots of options for snorkeling and diving the coral reefs and historic wrecks. The leeward coastline has lots of easy cruising and calm anchorages with chances to step ashore for a range of activities, whether rum tasting at one of the island’s historic distilleries, enjoying a gourmet dinner at Le Zandoli (hosting chefs who worked in French Michelin-starred restaurants) or simply relaxing at one of the best beaches, like Anse des Salines.