The Caribbean is one of the world’s most popular destinations for bareboat sailing, offering steady trade winds, short island hops, and countless protected anchorages. From the laid-back charm of the British Virgin Islands to the untouched beauty of the Exumas and the dramatic volcanic scenery of the Windwards, these routes combine easy navigation with unforgettable experiences both on and off the water. 👇👇👇👇👇 Discover the Caribbean you love—join tens of thousands who get our weekly insider