292 Sailboats to Rent in the Caribbean

Sailboat charter in Caribbean

Three Reasons to Charter a Sailboat in the Caribbean

1. A Diver’s Haven

A sailboat charter gives you the chance to try diving and snorkeling as well, which are becoming favourites in the clear waters of the Caribbean islands, with magical marine life presenting an opportunity too good to miss out on! Whether an experienced diver or not, be sure to pack your gear on board your boat to ensure you can make the most of the wonders the Caribbean has to offer below the waves as well as above – note that snorkel equipment may be included in your charter price. Why not rent a boat and head to ‘The Blue Hole’ in Belize; a sink hole which is part of the Barrier Reef Reserve System (a UNESCO World Heritage Site) and has become an acclaimed dive site.

2. Blissful weather

Averaging 30°C most days, the tropical heat will ensure a truly gratifying sail. With consistent trade winds from the north east at 10 to 25 knots and warm waters, the conditions for a sailing holiday in the Caribbean could not look more tempting! The reliable weather (outside of hurricane season) will make for a stress-free sailboat charter so you will without doubt, be seduced by the exotic charms of the Caribbean Sea.

3. Spellbinding Scenery

A sailboat charter in the Caribbean is more than just sailing… the islands are a haven of lush greenery, with breathtaking volcanoes cloaked in dense rainforest, impressive waterfalls and sensational beaches. Rent a boat and head to the mystical ‘Boiling Lake’ in Dominica, or the stunning ‘La Mina Falls’ in Puerto Rico or the world-famous Grace Bay Beach on Providenciales island where powdery white sand and glittering, translucent, azure waters will make you feel like you’ve just sailed onto a postcard!

Caribbean Colonial Charm

The islands each have their own unique character and distinctive history, so take a few days to explore cities like Willemstad in Curaçao, where the vivid colours of Dutch colonial townhouses feel like a little slice of Europe in the tropics! Or organize your Caribbean sailboat charter from the Cienfuegos base, and before embarking on your nautical adventure, take a trip into Havana, Cuba’s very own time capsule. If you’re searching for real rustic charm, go and explore Turks and Caicos’ capital, Cockburn Town or the Dominican Republic’s Santo Domingo, home to the Caribbean’s oldest colonial district.

A Nature-Lover’s Paradise

Each Caribbean island is brimming with a different combination of beaches, rainforests, caves and reefs which are home to rich ecosystems with a jaw-dropping array of wildlife. Whilst navigating your sailboat through the tropical waters, look out for dolphins, stingrays and turtles. If your charter holiday starts in the Bahamas, you might be lucky enough to spot swimming pigs and flamingos, or maybe venture to St. Lucia and seek out the 14ft long St. Lucian Boa Constrictor!

Getting There

The Caribbean Islands have more than 50 international airports between them, many of which also offer internal flights, so reaching your sailboat charter base will be easy.

  • Antigua and Barbuda: V. C. Bird International Airport, located on the island of Antigua, 5 miles northeast of the capital, St John’s.
  • Bahamas: Grand Bahama International Airport, located in Freeport, Bahamas.
  • British Virgin Islands: Terrance B. Lettsome International Airport, located on Beef Island - just off the main island of Tortola.
  • Martinique: Martinique Aimé Césaire International Airport, located in Le Lamentin in the capital Fort-de-France.