Good for

  • Cruising
  • Exploration
  • Ocean passages
  • Training
  • Wildlife
  • Winter sun
  • Sun
  • Racing

Duration

  • 2 - 6 days
  • 1 week +
  • 2 weeks +

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.

Wildlife

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

Caribbean Christmas Sailing Grenada to St Lucia

Enjoy the beauty of the colourful Caribbean islands at Christmas with luxury yacht Chronos as she sails from Grenada to St Lucia.
  • Vessel: Chronos
  • Where: Grenada
  • Duration: 7 days
  • Date: 22 December 2021

Caribbean New Year Sailing in Antigua & Barbuda

Bring the New Year in with style onboard Rhea as she sails and explores Antigua & Barbuda.
  • Vessel: Rhea
  • Where: Caribbean
  • Duration: 11 days
  • Date: 28 December 2021

Sailing in the Caribbean; Exploring the Grenadines

Sail with luxury yacht Skyelark to explore the Caribbean from St Lucia.
  • Vessel: Skyelark
  • Where: Caribbean
  • Duration: 10 days
  • Date: 10 January 2022

Caribbean Tall Ship Sailing

Sail the turquoise Caribbean waters with Eye of the Wind as she makes her way around the island of Guadeloupe.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 21 January 2022

Caribbean Tall Ship Sailing

Enjoy winter sun Caribbean sailing from Guadeloupe to Martinique on a luxury tall ship, Eye of the Wind.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 28 January 2022

Caribbean Tall Ship Sailing

Experience the Caribbean way of life on Eye of the Wind as she sails to explore the island of Martinique, St Vincent & the Grenadines.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 4 February 2022

Sailing in the Caribbean; Exploring the Grenadines

Sail with luxury yacht Skyelark to explore the Caribbean from St Lucia.
  • Vessel: Skyelark
  • Where: Caribbean
  • Duration: 10 days
  • Date: 10 February 2022

Caribbean Tall Ship Sailing

Enjoy winter sun Caribbean sailing from Martinique to Guadeloupe on luxury tall ship, Eye of the Wind.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 11 February 2022

Caribbean Tall Ship Sailing

Live the Caribbean dream on board Eye of the Wind as she island-hops from Guadeloupe to St Martin exploring the turquoise waters of the Caribbean Sea.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 18 February 2022

Sailing in the Caribbean; Exploring the Leeward Islands

Sail with Skyelark to explore the Leeward islands of the Caribbean in luxury.
  • Vessel: Skyelark
  • Where: Caribbean
  • Duration: 10 days
  • Date: 24 February 2022

Sailing in the Caribbean; Exploring the Grenadines

Sail with luxury yacht Skyelark to explore the Caribbean from St Lucia.
  • Vessel: Skyelark
  • Where: Caribbean
  • Duration: 10 days
  • Date: 10 March 2022

Sailing in the Caribbean; St Lucia to Antigua

Sail with Skyelark to explore the Leeward islands of the Caribbean in luxury.
  • Vessel: Skyelark
  • Where: Caribbean
  • Duration: 10 days
  • Date: 4 April 2022

Atlantic Crossing Expedition Sailing

Spend 33days at sea with tall ship Blue Clipper as she makes her way across the Atlantic from the coast of Portugal to the Caribbean island of Grenada.
  • Vessel: Blue Clipper
  • Where: Atlantic Crossing
  • Duration: 33 days
  • Date: 8 November 2022

Winter Sun Sailing in the Caribbean

Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed!
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 8 days
  • Date: 12 December 2022

Christmas & New Year Sailing in the Caribbean

Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed!
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 10 days
  • Date: 22 December 2022

Winter Sun Sailing in the Caribbean

Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed!
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 11 days
  • Date: 4 January 2023

Sailing in the Caribbean; Grenada to Antigua

Enjoy 11 days of Caribbean sailing on tall ship Blue Clipper as she island-hops from Grenada to Antigua.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 11 days
  • Date: 16 January 2023

Sailing in the Caribbean around Antigua

Discover the Caribbean island of Antigua under sail with tall ship Blue Clipper.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 8 days
  • Date: 28 January 2023

Sailing in the Caribbean around Antigua

Discover the Caribbean island of Antigua under sail with tall ship Blue Clipper.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 8 days
  • Date: 5 February 2023

Sailing in the Caribbean; Antigua to Tortola, BVI

Sail the Caribbean from Antigua to Tortola, BVI with tall ship Blue Clipper
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 11 days
  • Date: 14 February 2023

Winter Sun Sailing in the Caribbean

Sail and discover the Caribbean magic of the British Virgin Islands with tall ship Blue Clipper from Tortola.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 8 days
  • Date: 27 February 2023

Winter Sun Sailing in the Caribbean

Sail and discover the Caribbean magic of the British Virgin Islands with tall ship Blue Clipper from Tortola.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 8 days
  • Date: 8 March 2023

Winter Sun Sailing in the Caribbean

Sail and discover the Caribbean magic of the British Virgin Islands with tall ship Blue Clipper from Tortola.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 8 days
  • Date: 17 March 2023

Atlantic Crossing Expedition Sailing

Spend 36days at sea with tall ship Blue Clipper as she makes her way across the Atlantic from the Caribbean island of Tortola to the West Coast of Scotland.
  • Vessel: Blue Clipper
  • Where: Atlantic Crossing
  • Duration: 36 days
  • Date: 26 March 2023
Scotland-Kerrera-castle-sailing

Destinations

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

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Bessie-Ellen-Agnes-Sailing

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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