Where to Go on Your Caribbean Sailing Vacation

Where to Go on Your Caribbean Sailing Vacation

Decisions, decisions. Picking a Caribbean destination to charter a bareboat to is much like ordering dessert when faced with an extensive dessert menu in a high-end restaurant. You know that every dessert will be awesome no matter what you order and if you’re lucky you’ll even be able to try a couple. Sailing around the Caribbean is no different. You have the option of exploring a single island or country in depth, or if your curiosity powers your sails, you have the option of exploring more than one country. Now to sprawl out the map and begin making your plans.

Where to Go on Your Caribbean Sailing Vacation

The British Virgin Islands

The BVI is typically broached soon after the idea of sailing around the Caribbean enters the conversation. Traveller after traveller returns from the BVI with stories of having spotted dolphins, dropped an anchor and watched the sunset in the middle of the sea, and of course scuba diving around coral reefs. When you raise the jib sail and set sail you’ll be able to take in the beauty of each of the Virgin Islands. The islands of the BVI that are most frequented consist of Tortola, Virgin Gorda, Anegada, and Jost Van Dyke. If you’re seeking a bit more solitude, sail out to one of the 50 lesser known islands that also make up the archipelago that are the British Virgin Islands.

The Bahamas

Just South of Florida, over 700 islands, cays, and islets, help make up The Bahamas. Despite its small stature (pop. 392,718), the Bahamas is one of the richest countries in the Americas, in regards to GDP per capita. Most of their money is brought in thanks to tourism and finance sectors. During you time soaking up the sun of The Bahamas you’ll have to visit the dolphins. If you don’t already interact with them enough while sailing, you can have an intimate experience with them when you get involved in the Bahamas’ dive program that brings friendly bottlenose dolphins and humans together in a humane environment.


Just a southern sail from the U.S. Virgin Islands is Antigua. Antigua & Barbuda boast 365 beaches within their jurisdiction. Once you’ve got your beach urges satisfied, sail over to the historic landmark of Nelson’s Dockyard National Park. It’s at this park that you’ll be able to see where the British fleet docked during the Napoleonic Wars. Special events are held almost daily at the park, as well as shops, bars, and restaurants. For a beautiful view, hike up to Shirly Heights and reward yourself with a cocktail and a live band.

This article was written by one of our contributing writers.


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