Sailboat Charter in the Caribbean

257 Sailboats to Rent in the Caribbean

The glorious white sand beaches and translucent turquoise waters of the Caribbean are only a few of many attractions that make these magical islands a perfect destination for a sailboat charter. With hundreds of dive and snorkel sites along navigation routes, this stunning archipelago really is a sailor’s dream! The 7000+ islands boast diverse culture, scenery and opportunities, making it one of the hottest new destinations for boat rentals. Set sail to Cuba and stroll through Havana’s colonial streets and soak up the contradictory ‘old vs. new’ ambience which governs this unique city, whilst sipping a mojito to the seductive rhythms of salsa. The Caribbean offers endless opportunities to make your charter more than just a sailing vacation, but an activity-packed cultural discovery!

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100% of our fleet is managed by certified professional charter companies that meet our quality and safety criteria. See Our Guarantee.

  1. Pogo 30 - Pogo (2015)Le Marin
    Capacity 6
    Cabins 2 cab
    Berths 6
    Engine 1x18hp
    Draught 1.05m
    Size 30ft

    Peter : I had a specific desire to sail a Pogo 30 after reading such great reviews on the ship. Globe Sailor is great for specific questio... read more

    from1 700 €*from 25/11 to 02/12View details
  2. Pogo 12.50 - Pogo (2014)Le Marin
    Capacity 8
    Cabins 3 cab
    Berths 8
    Engine 1x30hp
    Draught 1.20m
    Size 40ft

    Donald : The boat is very fast an in a good state. It's really a pleasure to sail the Pogo 12.50. At the beginning we had week winds (3-5 k... read more

    from3 600 €*from 25/11 to 02/12View details
  3. Ovni 365 - Ovni (2007)Pointe à Pitre
    Capacity 6
    Cabins 3 cab
    Berths 6
    Engine 1x40hp
    Draught ---
    Size 37ft
    from1 850 €*from 09/12 to 16/12View details
  4. Oceanis 34 - Beneteau (2011)Le Marin
    Capacity 8
    Cabins 3 cab
    Berths 6+2
    Engine 1x29hp
    Draught 1.37m
    Size 34ft
    from1 290 €*from 29/09 to 06/10View details
  5. Sun Odyssey 49 - Jeanneau (2004)Le Marin
    Capacity 8
    Cabins 3 cab
    Berths 6+2
    Engine 1x64hp
    Draught 2.15m
    Size 49ft
    from2 300 €*from 30/06 to 07/07View details
    • -5 %
    Harmony 42 - Harmony (2009)Pointe à Pitre
    Capacity 8
    Cabins 3 cab
    Berths 6+2
    Engine 1x56hp
    Draught 1.55m
    Size 42ft
    from 1 460 €1 387 €*from 18/08 to 25/08View details
    online booking
  6. Pogo 36 - Pogo (2017)Le Marin
    Capacity 8
    Cabins 3 cab
    Berths 8
    Engine 1x30hp
    Draught 1.20m
    Size 36ft
    from2 600 €*from 25/11 to 02/12View details
    • -5 %
    Oceanis 423 - Beneteau (2004)Cienfuegos
    Capacity 6
    Cabins 3 cab
    Berths 6
    Engine 1x56hp
    Draught 2.10m
    Size 43ft
    from 1 360 €1 292 €*from 06/10 to 13/10View details
    online booking
  7. Ovni 395 - Ovni (2005)Pointe à Pitre
    Capacity 8
    Cabins 3 cab
    Berths 6+2
    Engine ---
    Draught 0.65m
    Size 40ft
    from2 000 €*from 25/11 to 02/12View details
    • -5 %
    Sun Odyssey 39i - Jeanneau (2010)Le Marin
    Capacity 8
    Cabins 3 cab
    Berths 6+2
    Engine 1x40hp
    Draught 2.00m
    Size 39ft
    from 2 060 €1 957 €*from 15/09 to 22/09View details
    online booking
Indicative price excluding any discounts and options

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.
  • BVI: 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.
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