What sailing regions to visit in the Caribbean?


Sail off to popular destinations such as the British Virgin Islands!


Visit sailing regions such as Cuba or Puerto Rico!


Whatever Caribbean sailing spot you choose, have a pleasant journey!


Where to sail in the Caribbean?

Greater Antilles - sailing destination Caribbean

Top Sailing Region: Greater Antilles

If you are wondering where to sail in the Caribbean, the Greater Antilles are one of the choices for you. They include the islands of Cuba, Hispaniola (Haiti and the Dominican Republic), Jamaica and Puerto Rico, together with the Cayman Islands. Situated north of the Lesser Antilles, they constitute almost 90% of the land mass of the West Indies. Cuba enchants with its serene waters and amazing scenery and is one of the most favorite sailing destinations in the Caribbean. Although beautiful, the islands of Jamaica and Hispaniola can pose certain safety issues on a sailing trip. Puerto Rico has a developed infrastructure for yachts and includes the Spanish Virgins which are just as beautiful as the US and British Virgins, but not as crowded.

Lesser Antilles - sailing destination Caribbean

Top Sailing Region: Lesser Antilles

Also known as the Caribbees, the Lesser Antilles are a frequently-visited sailing region in the Caribbean. They include the Leeward Islands, the Windward Islands, Barbados and the Netherlands Antilles. The British Virgin Islands, one of the Leewards, are among the safest and most popular sailing regions in the world. Apart from sailing, the waters are great for swimming, diving and snorkeling. Antigua and Barbuda boast wonderful scenery and great anchorages. Martinique, St. Lucia, St. Vincent and the Grenadines and Grenada are where you want to sail in the Windwards. Martinique has many secluded bays and is perfect for sailing. All of the islands boast splendid white beaches and turquoise waters.

Featured Caribbean charter bases

Port de Lonvilliers sailing

Port de Lonvilliers

The prime yacht charter facility on the island of St. Martin featuring a restaurant, several shops and boutiques.

Marina Bas-du-Fort - rent a boat

Marina Bas-du-Fort

This Guadeloupe charter base offers moorings for all yacht types and sizes, all with water and power connections.

Cienfuegos Marina - charter a yacht

Cienfuegos Marina

Located on the southern coast of Cuba, this 36-berth marina offers all necessary facilities and services.

Other charter destinations

If you are thinking about another location apart from the Caribbean to charter your yacht in, explore our pages on different charter spots in Europe. Visit A Yacht Charter Dubrovnik and find out what this beautiful Croatian city has to offer. Discover other Adriatic jewels such as Zadar and Split or read more about the top Greek sailing region of Athens. Visit A Yacht Charter Marmaris and find out why this amazing Turkish destination is so popular for yacht charter. Browse through A Yacht Charter Ibiza and discover the beauties of this top charter spot.