The Caribbean by Yacht: Underrated Islands to Explore in 2026

The Caribbean is a yachter’s paradise with over 5,000 islands, islets, and cays with white sandy beaches, spread across more than a million square miles of brilliant blue water with coral reefs and abundant marine life. Of course, on land, you can explore rich cultures and tropical landscapes, some with natural hot springs and cascading waterfalls framed by lush greenery.

From the Windward and Leeward islands to the Mexican Caribbean, when planning your 2026 yacht trip, you have so many to choose from that it can feel a bit overwhelming. While popular islands like Jamaica and the Dominican Republic may be some of the first that come to mind, there are plenty of other Caribbean Islands worth discovering by yacht that you might not have considered. 

Dominica

Known as the “Nature Island,” Dominica is a nature lover’s paradise. There are just two main anchorages, Roseau at the southern end and Portsmouth at the northern point. In exchange for the limited tourism development, you’ll enjoy some of the most unspoiled, spectacular landscapes. Dominica is not only one of the greenest islands in the Caribbean, but it’s home to numerous waterfalls, hot springs, volcanic features like fumaroles and mud baths, and black sand beaches. Plus, National Geographic recently named it among the world’s best islands to visit in 2026, highlighting its sperm whales, with around 200 here all year-round. Divers can even swim with them. 

Dominica is one of the top islands for snorkeling, with reefs home to species that are rarely seen in the Caribbean, including seahorses, flying gurnards, and frogfish. Rays, sea turtles, and Caribbean reef squid are just a few of the other creatures you might spot. If you’re up for a challenging hike, take the 4-mile trek to Boiling Lake. Those who would prefer to avoid the difficult terrain will be able to take the new cable car that opens in 2026 to reach it instead.

Bequia

Bequia is a dream for sailors with unspoiled, authentic Caribbean charms, minus the high-rise resorts and crowds. Admiralty Bay is one of the most picturesque, protected natural harbors in the Caribbean for safe anchorage with breathtaking views. Anchor at the southern end, and you’ll be just steps from beautiful beaches. If you want to leap into the water, the snorkeling is outstanding, with all sorts of tropical fish, octopus, eels, and more. 

Along the popular waterfront path known as Belmont Walkway, you’ll find seafood shacks, beach bars, and restaurants, with rum punch always flowing while the sounds of reggae and the waves provide the perfect backdrop for relaxation. There’s also a rich sailing tradition on Bequia, including historic boat building, along with well-stocked markets for picking up provisions.

Mustique

If you’re looking for something ultra-exclusive, Mustique is a hideaway for celebrities, royalty, and all sorts of elite that you might rub elbows with down at Basil’s, the local bar. Just about everyone gathers here just before sunset to watch the colorful show in the sky and enjoy the live music while sipping on cocktails and dining on lobster. Despite attracting the rich and famous, it’s a chic place for letting loose without any pretentiousness, focused on understated elegance and simple pleasures, unlikely many of the busier islands.

Of course, you can enjoy the quintessential Caribbean activities here too, with beautiful white sandy beaches and crystal-clear blue waters ideal for snorkeling, diving, and paddleboarding. The top place to anchor is Britannia Bay, with mooring buoys for easy access to the beach and iconic Basil’s Bar.

Jost Van Dyke, British Virgin Islands

The only way to access Jost Van Dyke is by water, with no airport here. That also helps keep the crowds away, but you can still enjoy a lively time at the famous Soggy Dollar. One of the most famous beach bars in the British Virgin Islands, it’s the place where the Painkiller cocktail was created—enjoy it while sitting on a bar seat that floats in the sea. With mooring balls in White Bay, you can stay overnight to experience the island at its most tranquil, after the day trippers have gone. It also happens to be one of the most jaw-dropping beaches on the island, with powdery white sands backed by palm trees and lapped by electric blue water.

Prickly Pear & Virgin Gorda, British Virgin Islands

The tiny, uninhabited island of Prickly Pear is protected by a national park in the North Sound of Virgin Gorda. You can anchor on the southwest side near Vixten Point, well-sheltered in easterly winds while offering access to beach facilities. The stretches of sand are blindingly white, and the turquoise water is incredibly clear, perfect for relaxation and swimming. When you’re in need of more, the main town on Virgin Gorda, Spanish Town, is less than a 30-minute sail away. You can also take advantage of the opportunity to visit The Baths, a stunning natural wonder made up of massive granite boulders with tunnels, grottoes, and tidal pools for refreshing dips. 

Antigua

Antigua is a favorite in the Leeward Islands with natural harbors and a beach for every day of the year. It’s a place for blissful relaxation and a playground for thrills, including kitesurfing off Jabberwock Beach. You might even sign up for the Super Yacht Challenge Antigua (SYCA), which runs throughout the sailing season. Anchor off Galleon Beach to watch for sea turtles and snorkel, or enjoy more protected shelter and amenities at Falmouth Harbour. It has world-class marinas and provides easy access to historic Nelson’s Dockyard, a UNESCO World Heritage Site with beautifully restored Georgian architecture, galleries, shops, and restaurants. 

It’s worth visiting Barbuda, Antigua’s smaller sibling, as well. The island is home to a pink sand beach that stretches for 17 miles and Codrington Lagoon, inhabited by the largest frigate bird colony in the western hemisphere and only accessible by boat.

Barbados

Barbados is one of the best all-around Caribbean islands, with some of the most beautiful beaches and tastiest drinks—after all, the rum is distilled right on the island. While you’ll probably enjoy plenty of rum cocktails, the food scene is impressive too. The national dish, Flushing Fish and Cou-Cou, is a must-try, as is the fresh grilled seafood at Oistins Fish Fry, which is best washed down with the local rum punch.

Port St. Charles Marina is the ideal place to land, with two beaches, including St. Charles Beach, which is right next to the breakwater berths for easy access to sunbathing, fishing, swimming, and snorkeling among seahorses and turtles. But you’ll want to visit Crane Beach on the Atlantic coast, best reached by taxi or car. It’s been named among the world’s best, with pink sands, translucent turquoise water, and a backdrop of dramatic cliffs. 

Iles des Saintes, Guadeloupe

Iles des Saintes (or Les Saintes) is one of the small group of islands that are part of the French-Caribbean archipelago of Guadeloupe, on the fringes of the Lesser Antilles. UNESCO-listed Les Saintes Bay, often ranked among the world’s most beautiful bays, offers sheltered anchorage and views of colorful Creole houses where you’ll notice a surprisingly chic, European feel.

In the town of Les Saintes, you’ll find authentic French-Creole dishes served in laid-back eateries, the perfect way to fuel up after a day on Pain de Sucre Beach. Located beneath the watchful eye of Fort Napoleon, here you can relax, swim, snorkel among sea turtles, and explore coral reefs home to abundant tropical fish like butterflyfish and blue tangs. 

Grenada

If you can plan an early February sailing trip to Grenada, you can join in the fun commemorating the island’s independence on February 7, when there will be celebrations throughout the local communities with food, music, and entertainment. But no matter when you visit this island, you can look forward to experiencing authentic Caribbean life and untouched beauty. Anchor at Grand Mal Bay or Prickly Bay for protection from the wind and close proximity to amenities. Some of the top beaches include the two-mile-long Grand Anse, home to the Underwater Sculpture Park with over 60 sculptures, just outside the capital of St. George. 

There’s lots of delicious food to enjoy throughout the island, with dishes incorporating the island’s spices, like ginger, cinnamon, cloves, nutmeg, and allspice, from Jerk Chicken to Oil Down, a hearty one-pot stew with breadfruit, callaloo, and salted meat in coconut milk.

St. Martin

Split between the French north and Dutch south, with no visible border, St. Martin is a 37-square-mile island known for its elegant mix of European and Caribbean. Marigot Bay on the French side provides protected anchorage and a rich culture to explore, with lively markets and mouthwatering cuisine. For tranquil days at the beach, anchor off Tintamarre and Ile Pinel. Of course, you don’t want to miss the Insta-famous Maho Beach, where you can take in a surreal sight with the planes landing right overhead. 

St. Martin also offers a central location for itineraries that include St. Barth’s, Anguilla, and Antigua. If you like to dive, don’t miss the small volcanic island of Saba.

St. Barth’s

Speaking of St. Barth’s, it’s a destination of its own as one of the most sought-after among the yachting community in the Carribean. Gustavia is the main port and most popular spot for yachts to anchor, filled with designer shops, upscale boutiques, galleries, and fine dining restaurants. While there’s lots of glitz and glamour, including the chance of celebrity spotting, you’ll find plenty of outdoor adventure to enjoy here too. 

There are nearly endless bays to choose from around the island for enjoying a variety of watersports, while hiking trails can be explored onshore. For a day at the beach, anchor off one of those most idyllic stretches like the pristine white sands of Colombier, tucked into a secluded cove accessible only by boat (or on foot). Part of a protected marine reserve, it’s especially good for snorkeling among sea turtles. 

Isla Mujeres, Mexico

Isla Mujeres is one of the best in the Mexican Caribbean for yachters as a popular sailing hub just a short hop from Cancun, yet much more laid-back and charming, with colorful streets, friendly locals, and beach clubs for drinks and lunch. It’s also home to one of the Yucatan’s most breathtaking beaches, Playa Norte. Curving around the northern coast, the chalk-white sands are lapped by calm, aquamarine waters with outstanding snorkeling near the reef. You’ll also find lounger and umbrella rentals, although bars and restaurants offer them complimentary to customers. Carefully navigate to anchor nearby, or moor at the full-service Marina Isla Mujeres and rent a golf cart to get there.