Caribbean Sailing Vacations
Choosing where to go on one of our Caribbean yacht charters is like choosing your favourite chocolate from the selection box. There is something for everyone; from the archipelagos of the British or US Virgin Islands, the diverse cultural differences of the Windward Islands; some of the world’s best scuba and snorkelling and, of course, many other fantastic things to do on your sailing vacations.
Wherever you choose, you’ll find a Sailo yacht or Caribbean catamaran charter to make your visit unforgettable. After all, the Caribbean looks great from the beach, but to really enjoy the region in all its tropical beauty, take to the seas!
Great sailing conditions
The Caribbean is well known as a nautical playground, with great opportunities for exploring by boat year round. One of the most popular ways to explore the region is with a Caribbean catamaran charter - meaning more space of deck to relax and soak up the sun. You’ll find yacht charters with Sailo to match your style and budget, with luxury motor yachts, beautiful sailboats and speedboats. Enjoy Caribbean sailing vacations, island hopping and exploring hidden bays, or simply find a boat for a day trip on a private party boat or fishing charter.
Discover the Caribbean your way
The islands of the Caribbean each have their own character and traditions, with a mixture of different colonial influences and local traditions, from the French character of Guadeloupe and Martinique, to the quirky British traditions of Bermuda and Barbados.
With a week long Caribbean yacht charter, you can take your time to get to know the region and arrive in style to a new port every day. Find your dream tropical island, jump into that shining sea and say hi to the locals swimming around the plethora of coral reefs. And by night, enjoy a sundowner from the deck of your Sailo yacht charter and toast another perfect day in the Caribbean.
Browse Sailo for dream Caribbean yacht charters!
The British Virgin Islands (BVI)
Tropical paradise doesn’t come much more stunning than the British Virgin Islands. This archipelago, a British overseas territory, offers the opportunity to find some of the most unspoiled and beautiful landscapes in the region. It’s easy to see why celebrities and millionaires flock to the BVIs for their winter retreats, and with a Sailo yacht or catamaran charter you too can enjoy this stunning Caribbean destination at your leisure. Coast hop around Tortola, the biggest island, visit the Little Sisters, or head to remote Anegada for true seclusion.
The US Virgin Islands (USVI)
Although they are two halves of the same archipelago, the US Virgin Islands have an unmistakably American flavor. With US citizens not needing a passport to visit, the USVI’s attract American families escaping the winter and looking for some fun in the sun. What this means is you’ll find a more developed tourist infrastructure, as well as more affordable vacation essentials like hotels. When it comes to sailing vacations, the USVIs offer plenty of choice with a fantastic choice of Caribbean catamaran and yacht charters on Sailo.
The Windward Islands
The southern section of the Antilles includes St Lucia, Grenada, Barbados, Martinique, Trinidad and Tobago and St Vincent and the Grenadines. With names like that conjuring in images of exotic ports, pastel shaded buildings, smiling locals and shimmering seas, Caribbean yacht charters with Sailo in the Windward Islands are an appealing option. If you’re looking for one of the best places to enjoy amazing Caribbean sailing vacations, any of these islands are a great starting point.
The Leeward Islands
The northern section of the Antilles, the Leeward islands include the Virgin Islands, St Kitts and Nevis, Guadeloupe and Antigua and Barbuda. You’ll find colonial influences from the British, Dutch and French and plenty of local flavor added into the mix. The Leeward Islands are a true yachting paradise, with countless smaller islands to explore and often perfect yachting conditions. With a Sailo Caribbean catamaran charter in the Leeward Islands, you’ll be able to experience the best sailing vacations at your leisure.
Our Favorite Sailing Itineraries in the Caribbean