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.

View sailing schedule

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

Atlantic Crossing on a Tall Ship

Crossing the Atlantic ocean is one of life's biggest adventures. Sail from the island of Tenerife in the Canaries to the beautiful Caribbean shores of  Marigot in St Martin.
  • Vessel: Eye of the Wind
  • Where: Canary Islands/Caribbean
  • Duration: 29 days
  • Date: 13 November 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

Winter Sun Sailing in the Caribbean

Live the Caribbean dream on board Eye of the Wind as she sails from St Martin to Martinique exploring the turquoise waters of the Caribbean Sea.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 13 December 2020

Christmas & New Year Sailing in the Caribbean

Escape the holiday season madness to sail and explore the culture of the colourful Caribbean islands on Chronos as she journeys from St Martin to Tortola BVI
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 14 days
  • Date: 21 December 2020

Christmas & New Year Sailing in the Caribbean

Leave the stresses of Christmas & New Year behind as Eye of the Wind sails you around the islands of the Caribbean.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 12 days
  • Date: 21 December 2020

Sailing from 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: 8 days
  • Date: 22 December 2020

Caribbean Tall Ship Sailing from Grenada

Enjoy 12 days of Caribbean sailing on tall ship Blue Clipper as she explores Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 29 December 2020

New Years Sailing from 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: 8 days
  • Date: 29 December 2020

Caribbean Tall Ship Winter Sun 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: 7 days
  • Date: 2 January 2021

Sailing from 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: 8 days
  • Date: 8 January 2021

Caribbean Island Hopping Tall Ship Sailing

Live the Caribbean dream on board Eye of the Wind as she sails from Guadeloupe to Antigua, exploring the turquoise waters of the Caribbean Sea.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 8 January 2021

Caribbean Tall Ship Sailing from Grenada

Enjoy 12 days of Caribbean sailing on tall ship Blue Clipper as she explores Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 12 January 2021

Sailing from 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: 8 days
  • Date: 15 January 2021

Sailing & Whale Watching in the Dominican Republic

Sail in comfort and luxury as elegant yacht Chronos sails the coast of the Dominican Republic while whale watching & exploring hidden anchorages.
  • Vessel: Chronos
  • Where: Dominican Republic
  • Duration: 11 days
  • Date: 20 January 2021

Caribbean Sailing around Guadeloupe

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: 22 January 2021

Caribbean Tall Ship Sailing from Grenada

Enjoy 12 days of Caribbean sailing on tall ship Blue Clipper as she explores Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 26 January 2021

Caribbean Sailing Guadeloupe to Martinique

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: 29 January 2021

Sailing from 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: 8 days
  • Date: 5 February 2021

Caribbean Sailing around Martinique

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: 5 February 2021

Sailing & Whale Watching in the Dominican Republic

Sail in comfort and luxury as elegant yacht Chronos sails the coast of the Dominican Republic while whale watching & exploring hidden anchorages.
  • Vessel: Chronos
  • Where: Dominican Republic
  • Duration: 8 days
  • Date: 6 February 2021

Caribbean Tall Ship Sailing from Grenada

Enjoy 12 days of Caribbean sailing on tall ship Blue Clipper as she explores Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 9 February 2021

Sailing from 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: 8 days
  • Date: 12 February 2021

Caribbean Carnival Sailing from Martinique

Enjoy winter sun sailing and colourful Caribbean Carnivals from Martinique to Guadeloupe on tall ship Eye of the Wind.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 8 days
  • Date: 12 February 2021

Sailing & Exploring around 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: 8 days
  • Date: 19 February 2021

Caribbean Island Hopping from Guadeloupe to St Martin

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: 19 February 2021

Sailing & Whale Watching in the Dominican Republic

Sail in comfort and luxury as elegant yacht Chronos sails the coast of the Dominican Republic while whale watching & exploring hidden anchorages.
  • Vessel: Chronos
  • Where: Dominican Republic
  • Duration: 15 days
  • Date: 20 February 2021

Caribbean Tall Ship Sailing from Grenada

Enjoy 12 days of Caribbean sailing on tall ship Blue Clipper as she island-hops from Grenada to St Martin.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 25 February 2021

Expedition Sailing from the Caribbean to Bermuda

Become part of a tall ship crew as you sail the Atlantic from the Caribbean to the island of Bermuda.
  • Vessel: Eye of the Wind
  • Where: Caribbean/Bermuda
  • Duration: 11 days
  • Date: 1 March 2021

Expedition Sailing from Bermuda to the Azores

Become part of a tall ship crew as you sail the Atlantic from the island of Bermuda to the Azores.
  • Vessel: Eye of the Wind
  • Where: Bermuda/Azores
  • Duration: 20 days
  • Date: 12 March 2021

Sailing from the Caribbean to Bermuda

Experience life at sea on an authentic tall ship as you sail from the Caribbean to the island of Bermuda.
  • Vessel: Blue Clipper
  • Where: Caribbean/Bermuda
  • Duration: 11 days
  • Date: 13 March 2021

Caribbean Sailing from Antigua

Explore the beautiful Lesser Antilles chain of islands in the Caribbean from Antigua on luxury yacht Rhea.
  • Vessel: Rhea
  • Where: Antigua
  • Duration: 11 days
  • Date: 13 March 2021

Expedition Sailing from Bermuda to the Azores

Experience life at sea on an authentic tall ship as you sail from the island of Bermuda to the Azores.
  • Vessel: Blue Clipper
  • Where: Bermuda/Azores
  • Duration: 22 days
  • Date: 27 March 2021
CORNWALL coverack

Destinations

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

View destinations
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.

View fleet