The Caribbean is the winter half of the superyacht year. When the Mediterranean cools, the fleet crosses the Atlantic to the Lesser Antilles, where the trade winds blow steady and warm from December to April and the islands lie a short, line-of-sight hop apart. A charter here is taken by the week on a crewed yacht, in US dollars: short passages, white-sand anchorages, reef snorkelling and a beach bar at sunset. The grounds run from the easy cruising of the British Virgin Islands to the glamour of St Barths, the sailing heritage of Antigua and the wild beauty of the Grenadines. This is the complete guide to a Caribbean yacht charter: where to cruise, the season, the fleet and how to book.
The winter superyacht season
The Caribbean season runs December to April — the dry, breezy months when the north-east trade winds give steady sailing and the humidity drops. Charters are taken by the week, crewed, the whole yacht held for your party, and quoted in US dollars, with running costs on an APA much as in the Mediterranean. Distances are short: most cruising grounds are a day-sail or less from island to island, much of it in sight of land, which makes the Caribbean the gentlest, most relaxed superyacht cruising anywhere. The peak is the Christmas–New Year fortnight, when St Barths in particular fills with the world’s largest yachts.
Steady trade winds, short line-of-sight hops, and a beach bar at every sunset.
The British Virgin Islands
The British Virgin Islands are the most chartered waters in the world, and the easiest: a tight cluster of islands around the Sir Francis Drake Channel, almost all within sight of one another, with reliable wind and a sheltered anchorage every few miles. The headline stop is The Baths on Virgin Gorda, where house-sized granite boulders form grottoes and pools at the water’s edge. Add the sandbar bars of Jost Van Dyke, the reefs off Anegada and the quiet bays of Norman and Peter islands, and you have a week of short, simple, beautiful sailing.
St Barths & St Martin
St Barthélemy is the glamour of the Caribbean — a small French island of designer boutiques, hillside villas and the yacht-lined harbour of Gustavia, busiest of all over New Year when the superyacht fleet gathers. Neighbouring St Martin / Sint Maarten is the western gateway and a major charter base, half French and half Dutch, with the lagoon at Simpson Bay and the famous beach at the end of the airport runway. Together they make the social heart of a northern Caribbean charter.
Antigua & the Leewards
Antigua is the sailing capital of the eastern Caribbean — said to have a beach for every day of the year, and home to English Harbour and Nelson’s Dockyard, the restored Georgian naval base where the classic yachts gather each spring. South lie the lush Leeward and Windward islands — Guadeloupe, Dominica’s rainforest, the Pitons of St Lucia rising sheer from the sea — a greener, wilder run for those with more time.
The Grenadines & Tobago Cays
At the southern end of the chain, the Grenadines are the Caribbean at its most unspoilt — a scatter of small islands between St Vincent and Grenada with few roads and fewer crowds. The jewel is the Tobago Cays, a marine park where a horseshoe reef shelters a lagoon of turquoise water over white sand, turtles grazing the seagrass and nothing ashore but palm-fringed cays. It is the most beautiful anchorage in the Caribbean, and the reason many charter this far south.
The fleet, and how to charter
The Caribbean fleet is largely the Mediterranean fleet in its winter berth — crewed motor yachts and sailing yachts that cross the Atlantic each autumn — chartered by the week and quoted in US dollars, plus the APA. You join the yacht at a base such as Tortola in the British Virgin Islands, St Maarten or Antigua, and the captain shapes the week around the trade winds and your party. To charter, choose a yacht and send an inquiry: our desk confirms availability, the route and the price, and arranges everything before you commit.
