Check Availability

 
 

Caribbean Yacht Charters & Sailing Vacations

Sunsail has nine yacht charter bases in the region, two Flotillas and one sailing school, each with a unique and individual character. Sunsail’s Caribbean sailing vacations offer something for everyone, whether a novice or experienced sailor.

What all of our Caribbean sailing vacations have in common are warm and steady trade winds in picture perfect surroundings, plus plenty of great bars to chill out with a killer rum punch or three!

It’s up to you, choose between short and easy hops with line-of-sight sailing or more challenging open water passages. Wherever you go, you will find a warm welcome and terrific atmosphere on the worlds best yachts and sailboats. You are guaranteed to return home relaxed, refreshed and ready to start planning your next Caribbean sailing adventure.

 
  • St. Martin Sailing Vacations

    A Sunsail yacht charter vacation in St. Martin offers a terrific blend of easy island-hopping and more challenging open-water passages in a truly stunning location. With Dutch and French influences combining easily with the local Caribbean culture and the island’s reputation as somewhere that knows how to throw a good party, you can be assured of excellent food and live music wherever you end up.

    • Pristine Beaches
    • Fabulous Duty-free Shopping
    • Lively Resort Towns
    • Spectacular diving
    Explore St. Martin Sailing Vacations
  • Bahamas Sailing Vacations

    A Sunsail yacht charter from our base in the Abacos offers easy island-hopping from one deserted beach to the next in crystal clear waters.  An ideal choice for families and less experienced sailors, the sheltered cruising grounds of the Sea of Abaco are perfect for those who want to take life easy and enjoy a relaxed sailing vacation in the Bahamas.
     

    • Family friendly
    • Snorkeling in turquoise seas
    • Colonial harbors
    • Abundance of wildlife
    Explore Bahamas Sailing Vacations
  • British Virgin Islands Sailing Vacations

    The British Virgin Islands are rated as one of the world’s top cruising destinations. Along with some superb sailing and idyllic protected anchorages a yacht charter, flotilla vacation or sailing schools course in the BVI guarantees as much fun as you can handle – it’s the destination of choice for those who like a party as much as they like to sail.

    • Super sociable
    • Stunning anchorages
    • Line-of-sight navigation
    Explore British Virgin Islands Sailing Vacations
  • Grenada Sailing Vacations

    Our yacht charter base in Grenada takes you to “The Spice Island of the Caribbean”. A rolling, mountainous island, abundant with wildlife, sea life and plant life.  The island offers a world of itinerary options for sailors who are a bit more experienced and is the perfect placed to start your sailing vacation in the Windward Islands. Ideal for one way trips to St. Vincent.
     

    • Stunning scenery
    • Blue water sailing
    • One way sailing to St Lucia
    • Warm Caribbean welcomes
    Explore Grenada Sailing Vacations
  • Belize Sailing Vacations

    As you leave our base at Laru Baya you will begin a journey like no other. With ancient Central American sites and an array of tropical creatures on land, you will sail from bay to bay through untouched crystal clear turquoise seas teaming with aquatic life, a yacht charter in Belize is a breathtaking experience not to be missed.

    • Snorkeling and Diving
    • On land wildlife and historical sites
    • Untouched white sand beaches
    Explore Belize Sailing Vacations
  • Antigua Sailing Vacations

    Antigua offers the perfect choice if your looking to mix the Caribbean party lifestyle with great sailing and stunning white sand beaches (365 to be exact, one for each day of the year!). With warm, steady trade winds and so many idyllic safe harbors, Antigua is a fantastic Caribbean yacht charter destination. 

    • Caribbean party lifestyle
    • Warm trade winds
    • 365 sandy beaches
    • Antigua Race Week
    Explore Antigua Sailing Vacations
  • St. Lucia Sailing Vacations

    Experience St Lucia: The Jewel of the Windwards. Offering stunning views, picturesque harbours, lush rainforest and a spectacular dormant volcano you can actually venture inside, a sailing vacation here is the perfect place to begin your exploration of the beauty and riches the Caribbean has to offer.

    • Beautiful white sandy beaches
    • Breathtaking views
    • Superb sailing conditions
    • Underwater wildlife
    Explore St. Lucia Sailing Vacations