Top 10 Caribbean Yacht Charter Destinations: Where to Go for Your Private Winter Charter

The Caribbean has hundreds of islands, and each one offers a different kind of holiday. Some are made for long lunches and lively evenings ashore, others for empty beaches, coral reefs and quiet nights at anchor. Choosing the right area is the first and most important step in planning your Caribbean yacht charter.

Here are our ten favourite Caribbean yacht charter destinations, with what makes each one special, who it suits best and where your yacht usually starts.

1. British Virgin Islands

Best for: first-time charterers, families and sailing lovers

The BVI are the classic Caribbean cruising ground. More than fifty islands lie close together around a sheltered channel, so passages are short and every afternoon brings a new anchorage. Highlights include the giant granite boulders of The Baths on Virgin Gorda, the flat coral island of Anegada with its endless beaches, and the relaxed beach life of Jost Van Dyke. Read our full British Virgin Islands yacht charter guide.

2. St Barths

Best for: fine dining, beach clubs and festive weeks

St Barths brings French elegance to the Caribbean. Gustavia’s small harbour is lined with boutiques and restaurants and fills with superyachts every winter, while Anse de Colombier offers a peaceful marine reserve reached only by sea or on foot. It is the most famous place in the Caribbean to spend New Year. Read our full St Barths yacht charter guide.

3. St Martin & Anguilla

Best for: beach days and food lovers

St Martin is shared by France and the Netherlands, and its seaside village of Grand Case is known for its restaurants and small open-air grills. Just to the north, Anguilla is a low, peaceful island with some of the finest sand in the Caribbean, plus tiny offshore cays such as Sandy Island and Prickly Pear Cays. Both combine perfectly with St Barths in one week. From February to June, humpback whales pass through these waters, so keep a lookout from the deck.

4. Antigua & Barbuda

Best for: yachting heritage and uncrowded beaches

Antigua is the home of Caribbean yachting. Nelson’s Dockyard in English Harbour, a UNESCO World Heritage Site, brings 18th-century naval history to life, and the island hosts some of the region’s most famous regattas. A short crossing north, Barbuda offers miles of empty, pink-tinged beach and a large colony of frigatebirds. Read our full Antigua yacht charter guide.

5. St Vincent & the Grenadines

Best for: seclusion, snorkelling and island hopping

The Grenadines feel like the Caribbean of the past. Bequia has a strong seafaring tradition, Mustique is discreet and exclusive, and the Tobago Cays, five uninhabited islets inside a horseshoe reef, are one of the best places in the region to swim with sea turtles.

6. Bahamas – The Exumas

Best for: turquoise water and unusual wildlife

The Exumas are a chain of around 365 cays south-east of Nassau, surrounded by some of the clearest water on Earth. A week here can include the swimming pigs of Big Major Cay, the light-filled Thunderball Grotto, the protected Exuma Cays Land and Sea Park and countless sandbars that appear at low tide. Read our full Bahamas yacht charter guide.

7. US Virgin Islands

Best for: easy travel from the United States

For American guests, the US Virgin Islands are the most convenient Caribbean destination: no passport is needed for US citizens and there are direct flights to St Thomas. Around two-thirds of neighbouring St John is a national park, with quiet bays and a marked underwater snorkel trail. The BVI are just a short cruise away, so the two are often combined. Read our full US Virgin Islands yacht charter guide.

8. St Lucia

Best for: dramatic scenery and romantic charters

Few sights in the Caribbean compare with the twin volcanic peaks of the Pitons, a UNESCO World Heritage Site rising straight from the sea near Soufrière. Anchor beneath them for a swim, visit the nearby waterfalls and sulphur springs, and spend an evening in Marigot Bay, a deep, palm-fringed inlet surrounded by green hills. Read our full St Lucia and Martinique yacht charter guide.

9. Grenada

Best for: food, culture and diving

Known as the Spice Island, Grenada is famous for nutmeg, cocoa and rum, and a market visit or plantation tour is a highlight ashore. Below the surface, the underwater sculpture park off its west coast is one of the most unusual snorkelling and diving sites in the world. Grenada is also an excellent start or finish for a one-way charter through the Grenadines.

10. Guadeloupe & Les Saintes

Best for: French Creole character and varied cruising

Guadeloupe combines rainforest, waterfalls and long beaches with a distinctly French way of life. The small archipelago of Les Saintes, with its colourful village on Terre-de-Haut, is one of the most charming anchorages in the Caribbean, while the protected waters around the Pigeon Islets offer excellent snorkelling and diving.

More Caribbean Islands Worth a Visit

Beyond our top ten, these islands are excellent additions to a longer charter or a one-way route between island groups.

St Kitts & Nevis

Two green volcanic islands separated by a narrow channel. Visit Brimstone Hill Fortress, a UNESCO World Heritage Site on St Kitts, relax on the golden sand of Pinney’s Beach on Nevis, and berth at the modern superyacht marina of Christophe Harbour. The islands fit perfectly into a one-way charter between Antigua and St Barths.

Martinique

A French island with a lively Creole culture, rum distilleries and the dramatic Mont Pelée volcano. The bays around Les Trois-Îlets combine fine beaches with easy access to restaurants, and Diamond Rock rises straight from the sea off the south coast. Martinique combines well with St Lucia, just to the south.

Dominica

The nature island of the Caribbean, with rainforest, hot springs and rivers. Take a guided boat trip up the Indian River near Portsmouth, or snorkel at Champagne Reef, where volcanic bubbles rise from the seabed. Ideal for active guests who enjoy excursions ashore.

Turks & Caicos

South-east of the Bahamas, the Turks & Caicos Islands are known for long white beaches such as Grace Bay, shallow turquoise banks and a pleasant climate almost all year round. They are a beautiful extension to a Bahamas charter.

Montserrat

A small, quiet island with hiking trails, black-sand beaches and a dramatic volcano that last erupted in the 1990s. A rewarding day stop for guests who want to see a different side of the Caribbean.

How to Choose Your Caribbean Destination

• First charter or family holiday: the British Virgin Islands or the US Virgin Islands.
• Glamour and nightlife: St Barths combined with St Martin and Anguilla.
• Nature and seclusion: the Grenadines or the Exumas.
• History and regattas: Antigua and Barbuda.
• Romance and scenery: St Lucia, perhaps combined with the Grenadines.

Most charters focus on one region for the week, because it leaves more time in the water and less time cruising. Learn more in our complete Caribbean yacht charter guide, our month-by-month season guide and our guide to charter prices.

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