Caribbean Sailing Vacations
Fine white sandy beaches, palm trees swaying in the warm breeze and a shimmering cobalt sea like you’ve never seen before. Boating trip from the archipelagos of the British Virgin Islands or US Virgin Islands sailing to the diverse cultural differences of the Windward and Leeward Islands, there is something for everyone. Discover some of the world’s best scuba and snorkelling, welcoming smiles and, of course, perfect beaches on a Caribbean sailing vacation.
Wherever you choose to go, you’ll find a Sailo boat rental to make your visit unforgettable. After all, the Caribbean looks great from the beach, but to really enjoy the region in all it’s tropical beauty, take to the seas!
The islands of the Caribbean are well known as a world class nautical playground, with great opportunities for exploring by boat all year round. One of the most popular ways to explore the region is with a private yacht charter, meaning more space on deck to relax and soak up the sun and escape the crowds.
You’ll find Caribbean luxury yacht charters with Sailo to match your style, vacation plans and budget. Choose from luxury motor yachts, beautiful classic sailboats and catamarans, or hop aboard a thrilling speedboat ride for a day on the sea.
Enjoy island hopping and exploring hidden bays, set sail to uninhabited cays and islands, or simply hire a boat for a day trip, a private party boat or fishing charter. From a budget friendly sailing vacation, to an indulgent luxury experience, a Sailo yacht charter will fulfil your Carribean dreams.
The Caribbean islands each have their own character, with a mixture of different colonial influences blending with local traditions. From the French flavors of Guadeloupe and Martinique, to the quirky British traditions of Bermuda, Barbados and the BVI's.
With a week long Caribbean catamaran charter, you have full control and can take your time to get to know the region, arriving in style to a new port every day. Get adventurous and find your dream tropical island, jump into that shining sea and say “Hi” to the locals swimming around the plethora of coral reefs. By night, escape and relax, enjoy a sundowner from the deck of your Sailo yacht charter and toast another perfect day in the Caribbean!
Whether you’re looking for a captained yacht, or a bareboat catamaran or sailboat, browse Sailo for your dream Caribbean yacht charters.
Tropical paradise doesn’t come much more stunning than the British Virgin Islands in the eastern Caribbean Sea. This British overseas territory offers the opportunity to find some of the most unspoiled and beautiful landscapes in the region. Jost Van Dyke offers many sheltered bays and is dotted with beautiful hidden beaches. Enjoy lunch at one of the relaxing bars or restaurants and top it off with a visit to ‘Bubbly pool’, the island's naturally foaming sea pool!
With a Sailo yacht or catamaran charter, explore this stunning Caribbean destination at your leisure. Coast hop around Tortola, the biggest island, visit the Little Sisters, or head to remote Angeada for true seclusion.
The US Virgin Islands have an unmistakably American flavor and attract American families escaping the winter and looking for some fun in the sun. When it comes to sailing vacations, the USVI’s offer a fantastic choice of locations for Caribbean boat charters.
St. Thomas is known as a premier yacht charter marina in the Caribbean and offers a host of beautiful beaches and snorkelling opportunities. Why not support local business with one of Sailo’s family run private boat tours and head to Brewer’s bay for some of the best snorkeling and a chance to see Turtles and rays.
Get on one of the yacht charters in St. Thomas and cruise to Frydendal, small laid-back settlement of serene beaches and rich marine life. Coki Beach provides some of the best diving on the island. For more adventure places in USVI, explore the famous Wreck of Cartanza, at Shipwreck Cove on Buck island. Just one of the many stunning shipwrecks and coral reefs you can discover by snorkel or scuba in the USVI's.
Strictly speaking Bermuda isn’t in the Caribbean, but she maintains that tropical vibe. Lazy days on beautiful pink sandy beaches, fantastic fishing and friendly and laid back locals. To all intents and purposes, this is the Caribbean! Sailing in Bermuda means less in the way of island hopping, and more fishing charters or exploring shipwrecks with snorkels or scuba gear. With a Bermuda private yacht charter you can explore the many islets along the coast and enjoy an unforgettable game fishing trip.
The southern section of the Antilles includes St Lucia, Grenada, Barbados, Martinique, Trinidad and Tobago and St Vincent and the Grenadines. These islands offer diverse Caribbean experiences, and a mixture of cultures and landscapes. The southern Caribbean also sees less hurricanes, making the Windward Islands an appealing option for an all year round Caribbean yacht charter.
St Vincent and the Grenadines makes a great base, offering east sailing plus access to St Lucia or Grenada. Sailo offers fantastic flexible options for either bareboat yacht charters, or for a more stress free experience, a captained choice enabling you to relax and fully enjoy your Carribean experience.
The Leeward islands include the Virgin Islands, St Kitts and Nevis, Guadeloupe and Antigua and Barbuda. Experience colonial influences from the British, Dutch and French and plenty of local flavor added into the mix. Sailing the Leeward Islands offer countless smaller islands to explore and often perfect sailing conditions, making them a perfect yachting destination.
With a Sailo Caribbean catamaran charter in the Leeward Islands, you’ll be able to experience these stunning sailing vacations at your leisure.
For a cultural hit, Nelson’s Dockyard National Park is a restored marina and is one of Antigua’s top sightseeing attractions. In the remote southeast, Half Moon Bay is great for both snorkeling and body surfing in it’s calm waters.
Whatever your itinerary, Sailo has everything you need to help plan your tailor made, flexible Caribbean experience.
Our Favorite Sailing Itineraries in the Caribbean