Leeward Islands

A boy is standing on the bow of a sailboat.

The Leeward Islands are a stunning chain of islands in the northeastern Caribbean, known for their calm turquoise waters, steady trade winds, and diverse mix of cultures and landscapes. Each island has something new to offer, whether it is Dutch, French, or independent. Stretching from the British Virgin Islands down through destinations like Saint Martin and Saint Kitt’s, and Saba, the region is famous for its protected anchorages, white-sand beaches, and ideal sailing conditions. The consistent winds and relatively short passages between islands make the Leewards one of the best cruising grounds in the world, while each stop offers its own character — from quiet coves and coral reefs to lively harbors and rich Caribbean history.

Explore our Leeward Islands Map

A group of girls sitting on a dock in front of a boat.

A group of people standing on top of a rocky hill.

A view of a bay with boats docked in it.

Three people sitting on top of a rock with mountains in the background.

A group of people holding drinks in front of a mural.

A green lizard sitting on top of a hill near the ocean.

A group of people walking down a trail in the jungle.

A woman is swinging on a tree in the forest.

A group of people standing on a bridge in the jungle.

A group of people hiking through the jungle.

A bridge over a hill with a castle in the background.

Two people walking through an archway in an old ruins.

A group of people playing a game of dominoes near the ocean.

A small mongoose is hiding behind some rocks.

Two people standing on a wooden platform in the ocean.

A view of the ocean from a hill overlooking a harbor.

A group of people walking along a path near the ocean.

Two people on a sailboat with mountains in the background.

A mountain range with a lot of trees on it.

A mountain in the ocean with a cloudy sky.

Two women sitting on the back of a sailboat in the ocean.

A woman standing on a railing in the jungle.

A woman and a boy are working on a piece of glass.

Find your Adventure

Each Sail Caribbean adventure focuses on a core activity like sailing, scuba diving, marine biology, or community service. But even more, every program offers a little of everything so you can unleash hidden talent, discover a new passion, and achieve your personal goals.

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