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What to expect from the weather on a Caribbean yachting vacation.

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Caribbean Weather

Our expertise is arranging fully crewed charters in popular cruising locations around the world. We are not weather experts but are often asked questions about the weather. Though we definitely consider that Caribbean weather patterns makes it a year-round destination, there are some factors to be aware of when planning.

Virgin Island Weather

There are two main parts of the Virgin Islands. The US Islands (USVI) include St. Croix, St. John, and St. Thomas, while the British Islands (BVI) are comprised of Jost Van Dyke, Tortola, and Virgin Gorda. Each island has its own distinct character, but they all share similar weather. Since two groups are near one another, it is likely you'll get to visit several of them in one trip!

While summer months are the hottest (in the 80s), December through February still garner lovely temperatures in the high 70s. The water temperature itself changes four to five degrees over the course of the year, but it never gets close to being cold. Compared to other regions in the Caribbean, Weather in the Virgin Islands may feel less humid than some other Caribbean ports because of the easterly trade winds.

The rainiest months are October and November; the driest are February and March. The high season starts in mid-December and goes through mid-April. Christmas and New Years often include what is referred to as "Christmas Winds," which add to the islands appeal because they are in generally more protected waters.

Customers largest Caribbean weather concerns are often about hurricanes so we should tell you that the highest concentration of storms in the area occurs in August and September with official hurricane season running from June to November. The good news about the rainfall here is that it primarily comes in short bursts and is over before you know it!

The fantastic temperatures, proximity of islands, and plethora of activities make these islands a great family destination.

Yachting Year-Round

The favorable Caribbean weather patterns and the availability of crewed catamarans and smaller sailing yachts in BVI waters remains fairly good throughout the year. However some owners choose to do their annual maintenance in or around August.

Leeward Islands Weather


The Leeward Islands are an exotic, Euro-style set of islands in the Caribbean that are almost too perfect to be believed. Anguilla, Antigua, Guadeloupe, Montserrat, St. Barts, St. Kitts & Nevis, and St. Martin/Maarten make up this island chain that runs between the Virgins and Dominica.

Typical of all Caribbean weather, these islands have no seasons to speak of, since the weather is fairly constant throughout the year. While traditional summer months are the hottest, December through February still see temperatures in the high 70s. The water temperature itself changes four to five degrees over the course of the year, but it never gets close to being remotely chilly!

The only surprise about the Leewards, a.k.a. the West Indies, is that they were formed in the midst of volcanic action and still retain vestiges of that history today. Christmas and New Years often experience the "Christmas Winds," which can be kind of harsh on the Leewards.

There is little humidity, and there are plenty of cool sea breezes. All in all, the Leewards are sophisticated and inviting with gorgeous, mountainous scenery. Pack your swimsuit, leave your raincoat, and don't forget the hiking shoes!

Grenadines Weather

The Windward Islands (also known as the Grenadines) are the southern portion of the Lesser Antilles, and they are deep in the heart of the Caribbean weather wise. This is a sublimely tropical climate fixed comfortably in the easterly trade winds. Introducing the Windwards: Barbados, Dominica, Grenada, Martinique, St. Lucia, and St. Vincent & the Grenadines!

The Windwards boast perfect sailing on account of their relationship to the wind. Wind from the northeast comes in at 15-25 knots, and these numbers get bumped up a bit around the first of the year with the sailor's gift commonly known as the "Christmas Winds." Some of the Windwards are a little less developed than elsewhere in the Caribbean, which may be a good thing.

There are two Caribbean weather seasons here. The rainy season is from June 1 to November 1, and the dry season accounts for the other seven months. Rain comes in short showers so you shouldn't be too bothered anyway. It's hard to have a bad day when the sun shines a near-constant 86 degrees! Visiting the tropical Windward Islands on a chartered yacht is about as good as it gets.


The highest possibility of storms in the Caribbean occurs in August and September; however, the official hurricane season runs from June to November. The hurricane season has a major effect on the types and volume of options available in different months and at different times in the Caribbean.
We'll help you plan the best time so your only worry is to remember to go home after your vacation.

The widest selection for all yacht options is between December and April when many captains votage south from the Bahamas, USA, or Mediterranean for the winter. However, these same options also return to their summer cruising grounds during hurricane season, which dramatically reduces the availability of megayachts and larger sailboats during the summer. Overall be sure that the captains are very familair with all Caribbean weather patterns to maximise their guest's enjoyment.

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