Every autumn, a large part of the world’s charter fleet crosses the Atlantic from the Mediterranean to spend the winter in the Caribbean. From December to April, steady trade winds, warm water and short hops between islands make it the leading winter destination for crewed yacht charter. Here is what to know if you are planning a charter this season.
When to Go
The main season runs from December to April. Christmas and New Year are the busiest weeks of the year, and yachts for those dates are in high demand. Many also require a longer minimum stay over the festive period. February and March offer reliable weather and slightly more choice, while late April and May bring quieter anchorages and good availability.
The hurricane season runs from June to November, which is why most yachts return to the Mediterranean for the summer.
Our advice: if you want to be on board for Christmas or New Year, start your search as early as you can. The best yachts for the festive weeks are often booked months ahead.
Where to Cruise
British Virgin Islands
Sheltered water and short passages, ideal for families and first-time charterers.
St Martin, St Barths and Anguilla
Glamorous harbours, fine dining and white-sand beaches, especially popular over New Year.
Antigua
Historic English Harbour and a bay for every day of the year, with Barbuda’s beaches nearby.
The Grenadines
Mustique, Bequia and the Tobago Cays, for a quieter, more remote escape.
How Caribbean Rates Work
Caribbean charter pricing can differ from the Mediterranean. Many Caribbean yachts, especially crewed catamarans, are offered on an all-inclusive basis, where food, most drinks and fuel for normal cruising are included in the price. Larger yachts are more often quoted plus expenses, with an Advance Provisioning Allowance (APA) paid in advance to cover running costs.
Local taxes and cruising fees vary by island, and a gratuity for the crew is customary at the end of the charter. We set out exactly what is and is not included before you commit.
Catamaran or Motor Yacht?
Crewed catamarans have become one of the most popular choices in the Caribbean. They are stable at anchor, spacious for their size, and their shallow draft reaches bays larger yachts cannot. Motor yachts cover more ground and suit guests who want more space, speed and water toys. We can help you weigh up the options for your group.
Planning a Caribbean charter this winter?
Tell us your dates and group, and we will send a shortlist of available yachts.
Get a shortlist on WhatsAppCaribbean destination guide
[…] As with any itinerary, your captain will adjust the route for the weather, the swell and your group’s pace. For a wider view of the season, see our Caribbean yacht charter guide for 2026–27. […]
[…] Allowance (APA). Our guide to yacht charter costs, APA and tips explains how it all works, and our Caribbean season guide covers the wider winter […]
[…] The charter season runs from December to April, outside the Atlantic hurricane season. Christmas and New Year are the busiest and most expensive weeks, and the best yachts for those dates book up early. January to March brings steady trade winds and lovely conditions, and the spring regattas add atmosphere in March and April. For more on timing and rates, see our Caribbean season guide. […]
[…] The season runs from December to April. Christmas and New Year are the busiest weeks. January to March offers steady breezes and settled weather, and the island’s famous sailing week brings a festival atmosphere in late April. For timing and rates across the region, see our Caribbean season guide. […]
[…] while February to April often brings the best balance of conditions and availability. See our Caribbean season guide for more on […]