Sailing Holidays in the Caribbean

Let one of our fleet whisk you off to explore the beauty of the Caribbean islands with an adventure sailing holiday. Climb the rigging and take in the view or simply relax on deck.

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The Caribbean boasts some of the greatest sailing grounds in the world. The wind, sunshine and numerous different islands and cultures make it one of our favourite destinations to explore under sail.

Making sure our sailing holidays in the Caribbean sit outside the usual hurricane season, our boats benefit from the warm North East trade wind belt that will carry you through the emerald islands of the West Indies.

Read our Top Ten reasons to visit the Caribbean here!

With our fleet – Skyelark, Chronos, Rhea, Twister, Blue Clipper and Eye of the Wind all making the annual sailing across the Atlantic, you won’t be short of choice for sailing these balmy waters. Whilst the harbours provide flat seas and sheltered anchorages you can marvel at how these ships handle the trade winds in open water, with the sails filled and the sea spray flying.


Spot graceful sea turtles gliding effortlessly through the water and Bottlenose Dolphins swimming with the wake of the bow. Stingrays waltzing the harbour walls and iguanas scuttling along the shorelines. Many different species of Whale also frequent the Caribbean sea, with the warm water providing the perfect breeding grounds at this time of year for the humpback whale.

Caribbean Palm tree beach

Birdlife in the Caribbean is an incredibly beautiful sight over 700 species of bird inhabiting the islands. 171 species alone are endemic to the region and found nowhere else in the world. From parrots to parakeets from hummingbirds to mockingbirds, keep your binoculars at the ready to spot these colourful delights. Pink Flamingoes are also a common bird across the Caribbean islands; these sociable creatures inhabit the blue lagoons, mudflats and lakes, living in colonies that can contain thousands of individuals.

Authentic Caribbean Sailing

The beauty of being on a ship in these breathtaking islands is that we can take you to the unspoilt, authentic Caribbean, away from the busy resorts and crowded beaches. Experience true Caribbean culture, from small fishing villages to lively colourful carnivals and beautifully breathtaking hidden anchorages. Wander the islands, swim with Sea Turtles and while away your evenings under the stars eating local cuisine cooked up by your onboard chef.

Sailing holidays in the Caribbean

Luxury Christmas Sailing in the Caribbean

Enjoy the beauty of the colourful Caribbean islands at Christmas with luxury yacht Chronos as she sails from Grenada to St Lucia.
  • Date: 21 December 2022
  • Vessel: Chronos
  • Duration: 8 days
  • Where: Grenada, Caribbean

Christmas Sailing in the Caribbean

Escape the holiday season to sail and explore the culture of the colourful Caribbean islands on Rhea as she journeys from St Martin to Tortola BVI
  • Date: 22 December 2022
  • Vessel: Rhea
  • Duration: 8 days
  • Where: St Martin, Caribbean

Luxury New Year Sailing in the Caribbean

Bring in the New Year with luxury and Caribbean sunshine with Chronos as she sails from St Lucia to Grenada
  • Date: 28 December 2022
  • Vessel: Chronos
  • Duration: 8 days
  • Where: St Lucia, Caribbean

New Year Sailing in the Caribbean

Bring in the New Year with Caribbean sailing on luxury yacht Rhea as she explores the British Virgin Islands
  • Date: 29 December 2022
  • Vessel: Rhea
  • Duration: 10 days
  • Where: BVI, Caribbean


Our range of vessels enables us to offer several destinations all over the globe. Which adventure will you choose?

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Our fleet

With vessels of all sizes and each with a unique history and construction, there is no shortage of choice for your sailing holiday.

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