Caribbean Yachting: Making The Most Of Every Season

If you’re wondering when to charter a yacht in the Caribbean, there’s a distinct yachting season, but that’s not to say you can’t charter in this tropical paradise year-round —if you know where and when to go. Let’s dive in.

By Jo Morgan • 11 October 2023

When is Peak Yachting Season in the Caribbean?

The yachting season in the Caribbean is at its most fabulous, fun-loving height during the Northern Hemisphere winter between December and May, with its peak between Christmas and March.

In early December, the yachts arrive in large numbers from the Mediterranean and pour down from North America to escape the icy winter. The Caribbean yachting season kicks off with the Antigua Yacht Show in the first week of December, and the charter season then peaks between Christmas and March, with the highest charter rates between Christmas and the end of January.

The season for motor yacht charters winds up in early to mid-April, but many sailing yachts stay on until the Antigua Sailing Week in late April/early May — a famously friendly affair which marks the close of the winter season.

What’s the Weather Like in the Caribbean in Winter?


Charterers in the Caribbean winter will enjoy the milder daytime temperatures of 82F (28C) and dive off the yacht’s swim platform into gloriously warm water temperatures of 80F (27C).

Sailors will get a kick out of sailing the winter trade winds, while motoryacht guests will enjoy the gorgeous sea breeze that breaks the heat of the afternoon. of course, wind often equals swell and chop, so the sea is less likely to be flat-calm in the wintertime.

However, the Caribbean has so many islands and archipelagos that your captain can always find a calm bay for swimming and watersports. A great example is the British Virgin Islands, which are well-sheltered and clustered very close together, so you can get away with very short cruises when the wind is up.

Can I Charter a Yacht in the Caribbean in the Summer?


Yes, absolutely! The Caribbean is a year-round cruising ground, and those who charter in summer will experience many benefits, including calmer seas and little wind. Charter rates and yacht availability are favourable, and there’s a packed calendar of local festivals and events to enjoy. Above all, you’ll have your pick of beautiful, quiet anchorages and top marina berths.

However, summer is the rainy season, and more importantly, hurricanes are likely forming in the region during this time. Hurricane season runs from June to November, with the highest risk historically falling between August and October.

Those worried about hurricanes have the option of chartering yachts in locations in the south of the Caribbean that fall outside the hurricane belt, such as Barbados and Trinidad and Tobago, or places that rarely see hurricanes, such as Costa Rica, Grenada, or St Lucia.

Temperatures in summer in the Caribbean average 82F (28C) degrees with highs in the low 100s (30Cs), but the humidity can be sweltering. That same humidity does cause the heat to break in the afternoons with brief tropical showers and storms — the perfect chance to grab a cocktail (or coconut juice) and sit on the aft deck watching the rain roll in. The summer trade winds also deliver a welcome cooling breeze.

The Caribbean offers a happy lifetime of cruising— a constellation of over 7,000 islands in an aquamarine sea. And for those looking to charter a yacht in the Caribbean, Bluewater can create an itinerary that takes in the best experiences, whatever time of year you want to travel!