Good for

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

Duration

  • 1 day
  • 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 under sail. 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 five of our fleet – 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 Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 28 January 2020

Caribbean Sailing St Lucia to Grenada

Sail from Grenada to St Lucia on luxury yacht Rhea as she explores the beauty of the colourful Caribbean islands.
  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 7 days
  • Date: 31 January 2020

Caribbean Sailing Grenada to St Lucia

Enjoy the beauty of the colourful Caribbean islands under sail as luxury yacht Rhea sails from Grenada to St Lucia.
  • Vessel: Rhea
  • Where: Grenada
  • Duration: 7 days
  • Date: 7 February 2020

Caribbean Sailing – the Paradise of the BVI

Discover the beauty and paradise of the British Virgin Islands as you sail with Eye of the Wind from Saint Martin across the Caribbean Sea.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 7 February 2020

Caribbean Sailing, Tobago to Martinique

Sail and explore the culture of the colourful Caribbean islands on Twister as she sails from Tobago to Martinique.
  • Vessel: Twister
  • Where: Caribbean
  • Duration: 10 days
  • Date: 10 February 2020

Caribbean Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 11 February 2020

Caribbean Sailing St Lucia to Grenada

Sail from Grenada to St Lucia on luxury yacht Rhea as she explores the beauty of the colourful Caribbean islands.
  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 7 days
  • Date: 14 February 2020

Caribbean Dreaming and Sailing around the BVI

Discover the paradise of the British Virgin Islands as you sail and explore these beautiful islands with Eye of the Wind.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 14 February 2020

Caribbean Sailing, Martinique to Antigua

Sail and explore the culture of the colourful Caribbean islands on Twister as she sails from Martinique to Antigua.
  • Vessel: Twister
  • Where: Caribbean
  • Duration: 10 days
  • Date: 21 February 2020

Caribbean Sailing from Grenada

Sail and explore the Caribbean island of Grenada on luxury yacht Rhea, anchoring in secluded bays and swimming in warm seas.
  • Vessel: Rhea
  • Where: Grenada
  • Duration: 7 days
  • Date: 21 February 2020

Caribbean Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 25 February 2020

Caribbean Sailing, Antigua to Tortola

Sail and explore the culture of the colourful Caribbean islands on Twister as she sails from Antigua to Tortola.
  • Vessel: Twister
  • Where: Caribbean
  • Duration: 10 days
  • Date: 4 March 2020

Caribbean Sailing from Grenada

Sail and explore the Caribbean island of Grenada on luxury yacht Rhea, anchoring in secluded bays and swimming in warm seas.
  • Vessel: Rhea
  • Where: Grenada
  • Duration: 6 days
  • Date: 7 March 2020

Caribbean Sailing Grenada to St Martin

Caribbean active sailing holiday onboard tall ship Blue Clipper from Grenada to St Martin.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 15 days
  • Date: 10 March 2020

Expedition from Tortola to Bermuda

A voyage for true sailors! Join Twister on the first leg of her expedition home sailing from Tortola to Bermuda.
  • Vessel: Twister
  • Where: Atlantic Ocean
  • Duration: 8 days
  • Date: 18 March 2020

Caribbean Sailing from St Lucia to Antigua

Explore the magic of the Caribbean islands on luxury yacht Rhea as she sails from St Lucia to Antigua.
  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 5 days
  • Date: 27 March 2020

Expedition from Bermuda to the Azores

A voyage for true sailors! Join Twister on the second leg of her expedition home sailing from Bermuda to the Azores.
  • Vessel: Twister
  • Where: Caribbean/Portugal
  • Duration: 17 days
  • Date: 28 March 2020

Caribbean Sailing St Martin to Antigua

Enjoy the azure ocean, palm beaches and the incomparable flair of the "Caribbean way of life" for spring sailing onboard luxury yacht Chronos.
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 11 days
  • Date: 28 March 2020

Ocean Sailing from Bermuda to the Azores

Cross the Atlantic ocean under sail on tall ship Blue Clipper as she sails from Bermuda to the Azores.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 25 days
  • Date: 11 April 2020

Atlantic Sailing from Gran Canaria to the Caribbean

Spend 32days at sea with tall ship Blue Clipper as she makes her way across the Atlantic from Gran Canaria to the Caribbean island of Grenada.
  • Vessel: Blue Clipper
  • Where: Canary Islands/Caribbean
  • Duration: 32 days
  • Date: 21 November 2020
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Destinations

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

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Tall Ships fleet

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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