Top 5 Caribbean Islands to Visit by Private Yacht This Winter
Winter is peak season for a Caribbean yacht charter — steady trade winds, warm sunshine, and calm seas make it the ideal time to explore the region’s most beautiful islands. Here are five destinations worth building into your itinerary this season.
1. British Virgin Islands
Often called the sailing capital of the world, the British Virgin Islands pack an extraordinary variety of anchorages into a compact area — from the granite pools of The Baths on Virgin Gorda to the legendary beach bars of White Bay on Jost Van Dyke. Short distances between islands and steady winds make it an easy, rewarding charter for both first-timers and experienced sailors.
2. Sint Maarten
Split between Dutch and French sides, Sint Maarten offers a lively, cosmopolitan base with excellent marinas at Simpson Bay and Port de Plaisance. It’s also a convenient gateway to nearby islands like Anguilla, Saint Barthélemy, and Saba — all within easy sailing distance.
3. St. Barth
Quieter and more exclusive than its neighbor Sint Maarten, St. Barth combines refined restaurants and boutiques with some of the most photographed anchorages in the Caribbean, including Gustavia and Colombier. It’s a favorite stop for guests seeking understated luxury over beach-bar energy.
4. The Grenadines
South of St. Vincent, the Grenadines offer a quieter, less-crowded alternative to the busier northern islands — think Bequia, Mustique, and the Tobago Cays marine reserve, known for its resident sea turtles and pristine reef. A great choice for guests who’ve already done the BVI and want something more off the beaten path.
5. Antigua & Barbuda
With a beach for every day of the year (or so the saying goes), Antigua combines historic English Harbour with an enormous variety of anchorages and beaches. It’s also a major hub for winter regattas and yacht charter activity, offering excellent infrastructure alongside genuinely beautiful sailing.
Planning a Multi-Island Winter Itinerary
Many of these destinations can be combined into a single trip — Sint Maarten and St. Barth in particular are just a short sail apart, and both connect easily to the wider Leeward Islands. If you’re chartering a crewed catamaran, your captain can help design a route that balances lively stops with quieter anchorages, tailored to your group’s pace.
Riviera Boat offers charters across all five of these destinations, with a fleet ranging from family-friendly Bali catamarans to premium Sunreef sailing yachts.
Ready to plan your winter itinerary? Explore our Caribbean yacht charter fleet and let us help you choose the right islands and yacht for your trip.