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 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

Sailing in the Caribbean; Exploring the Grenadines

Sail with Skyelark to explore the Caribbean in luxury from St Lucia.
  • Vessel: Skyelark
  • Where: Caribbean
  • Duration: 14 days
  • Date: 19 December 2021

Caribbean Christmas Sailing St Martin to Antigua

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 Antigua.
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 7 days
  • Date: 21 December 2021

Caribbean New Year Sailing in Antigua & Barbuda

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

Sailing in the Caribbean; Exploring the Grenadines

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

Sailing the Atlantic; Antigua to Gibraltar

Sail the Atlantic with luxury yacht Skyelark from Antigua to Gibraltar.
  • Vessel: Skyelark
  • Where: Atlantic
  • Duration: 28 days
  • Date: 26 April 2022
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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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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