A sailing holiday in the Caribbean is guaranteed to be memorable as the Caribbean boasts some of the greatest sailing grounds in the world, with the ever-present trade winds, year-round warm sunshine and a diverse selection of islands and cultures to explore. The dazzling turquoise waters here are home to beautiful coral reefs whilst the islands themselves offer lush green rainforests, white, soft sandy beaches and fabulous cuisine. A sailing holiday in the Caribbean provides the opportunity to explore this archipelago from a new perspective, far-away from the bustling tourist centres and busy beaches. Discover a more authentic side to these laid-back isles where warm hospitality and smiles are guaranteed.
Read our Top Ten reasons to take a sailing holiday in the Caribbean here!
Sustainable Sailing Holidays in the Caribbean
Those seeking a sustainable sailing holiday in the Caribbean will be spoilt for choice as a selection of our fleet all make the annual voyage across the Atlantic under sail. Guests can choose from a selection of luxury vessels including Skyelark , Chronos , Rhea , Blue Clipper and Eye of the Wind each offering an all-inclusive sailing holiday in the Caribbean without compromising on comfort or style. Whether you’re a first time sailor or hold a love for being at sea, a sailing holiday in the Caribbean provides a good mix or calm, flat seas as well as open-water sailing, allowing the chance to marvel these ships travelling in the trade winds in open water, with the sails billowing and the sea spray flying.
Our vessels here largely operate under sail which enables our skippers to introduce guests to a more authentic Caribbean, unspoilt by mass-tourism and over-crowded beaches. Step ashore from sheltered anchorages to experience true Caribbean culture; from small fishing villages to lively colourful carnivals and beautifully breathtaking hidden harbours tucked away under emerald green hills. Wander the islands, swim with sea turtles and while away your evenings under the stars eating mouth-wateringly tasty local cuisine freshly prepared by your onboard chef.
Wildlife in the Caribbean
The beauty of the Caribbean doesn’t just lure humans, the waters here teem with wildlife and a sailing holiday provides the best way to spy some of its marine inhabitants. Keen eyes will be rewarded with graceful sea turtles gliding effortlessly through the water, playful Bottlenose Dolphins swimming with the wake of the bow, humpback whales who visit the warm waters to breed as well as a variety of rays and colourful tropical fish. Iguanas scuttle along the shoreline whilst starfish, coral, conch’s and a plethora of crustaceans, shellfish and other marine life can all be discovered by those who look. Each of our vessels sail with snorkels and masks so take the opportunity to slip into these bath-like waters and watch the busy underwater world in action, you won’t be disappointed.
There is also a wealth of birdlife in the Caribbean with over 700 species of bird inhabiting the archipelago and 171 species endemic to the region, found nowhere else in the world. From parrots to parakeets, hummingbirds to mockingbirds, pink flamingos to pelicans, be sure to have your binoculars at the ready to admire these colourful, occasionally comical and utterly wonderful creatures.
Food and Drink in the Caribbean
Caribbean cuisine is as colourful and varied as the islands with distinct flavours reflecting their rich cultural history. Fusing together West African, Creole, Cajun, Amerindian, European, Latin American, Indian/South Asian, Middle Eastern, and Chinese (phew!) we guarantee dishes to set the tastebuds tingling. Our onboard chefs will prepare your meals each day using locally sourced produce wherever possible. Sample island-grown plaintains, sweet potatoes, cassava, chickpeas, cilantro, bell peppers and coriander along with freshly caught fish and seafood. Bright, colourful mouth-watering dishes packed with eclectic flavours served alfresco, the perfect accompaniment to a sailing holiday in the Caribbean.
If you have any dietary preferences or intolerances, please do advise us prior to travel so we can advise the boat in advance.
Read more about our sailing holidays in the Caribbean
For a more in-depth guide on the highlights of a sailing holiday in the Caribbean, head to our Journal where you can find a guide to sailing in Grenada , St Vincent and the Grenadines , and the British Virgin Islands .
Sailing holidays in the Caribbean
Luxury Sailing in the Caribbean
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 5 February 2023
Vessel : Chronos
Duration : 15 days
Where : Grenada, Caribbean
Luxury Yacht Sailing in the Grenadines
Sail and explore the Grenadines with luxury yacht Skyelark as she sails from St Lucia.
Date : 8 February 2023
Vessel : Skyelark
Duration : 10 days
Where : St Lucia, Caribbean
Tall Ship Sailing in the BVI, Caribbean
Discover the paradise of the British Virgin Islands as you sail and explore these beautiful islands with Eye of the Wind.
Date : 10 February 2023
Vessel : Eye of the Wind
Duration : 8 days
Where : British Virgin Islands
Tall Ship Sailing in the BVI, Caribbean
Discover the paradise of the British Virgin Islands as you sail and explore these beautiful islands with Eye of the Wind.
Date : 17 February 2023
Vessel : Eye of the Wind
Duration : 8 days
Where : British Virgin Islands
Luxury Sailing in the Caribbean
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 19 February 2023
Vessel : Chronos
Duration : 8 days
Where : Grenada, Caribbean
Luxury Sailing in the Caribbean
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to Martinique.
Date : 5 March 2023
Vessel : Chronos
Duration : 8 days
Where : Grenada, Caribbean
Offshore Ocean Passage from Bermuda to the Azores
Immerse yourself into life at sea with an offshore expedition sailing adventure on tall ship Eye of the Wind from Bermuda to the Azores.
Date : 8 March 2023
Vessel : Eye of the Wind
Duration : 20 days
Where : Bermuda/Azores
Luxury Caribbean Sailing from Martinique to Antigua
Luxury Caribbean sailing with tall ship Chronos from Martinique to Antigua exploring Dominica & Guadeloupe.
Date : 12 March 2023
Vessel : Chronos
Duration : 7 days
Where : Martinique, Caribbean
Luxury Sailing around Antigua & Barbuda
Explore the Caribbean island of Antigua and Barbuda with luxury classic yacht Chronos.
Date : 18 March 2023
Vessel : Chronos
Duration : 8 days
Where : Antigua, Caribbean
Luxury Easter Sailing in the Caribbean
Sail with luxury yacht Rhea this Easter as she discovers the Caribbean Leeward islands under sail.
Date : 5 April 2023
Vessel : Rhea
Duration : 10 days
Where : Antigua, Caribbean
Offshore Sailing Passage from Antigua to Gibraltar
Cross the Atlantic with luxury yacht Chronos as she sails from the Caribbean island of Antigua to Gibraltar on the south coast of Spain.
Date : 6 April 2023
Vessel : Chronos
Duration : 23 days
Where : Antigua/Gibraltar
Offshore Sailing Passage from Antigua to the Azores
Sail from the Caribbean island of Antigua to the Atlantic archipelago of the Azores with luxury yacht Rhea.
Date : 16 April 2023
Vessel : Rhea
Duration : 18 days
Where : Antigua/Azores
Luxury Yacht Sailing in the Caribbean
Explore the Caribbean with luxury yacht Skyelark from the island of Antigua to St Martin.
Date : 19 April 2023
Vessel : Skyelark
Duration : 10 days
Where : Caribbean
Offshore Sailing Passage from Gibraltar to Malta
Sail the Mediterranean Sea with luxury yacht Chronos from Gibraltar to the island of Malta.
Date : 27 April 2023
Vessel : Chronos
Duration : 7 days
Where : Gibraltar/Malta
Offshore Ocean Passage from Portugal to Grenada
Spend 34 days 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.
Date : 8 November 2023
Vessel : Blue Clipper
Duration : 34 days
Where : Portugal/Caribbean
Offshore Ocean Passage from Tenerife to the Caribbean
Sail with luxury yacht Rhea from Tenerife, across the Atlantic Ocean to the Caribbean island of St Martin.
Date : 28 November 2023
Vessel : Rhea
Duration : 23 days
Where : Canaries/Caribbean
Offshore Sailing Passage from Cape Verde to Grenada
Cross the Atlantic from Cape Verde to the Caribbean island of Grenada with luxury yacht Chronos.
Date : 4 December 2023
Vessel : Chronos
Duration : 15 days
Where : Cape Verde/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 : 20 December 2023
Vessel : Chronos
Duration : 8 days
Where : Grenada, Caribbean
Christmas Sailing in the Caribbean
Enjoy luxury Caribbean sailing with classic yacht Rhea as she sails from St Martin to Antigua.
Date : 21 December 2023
Vessel : Rhea
Duration : 8 days
Where : Lesser Antilles, Caribbean
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 to climb aboard!
Date : 22 December 2023
Vessel : Blue Clipper
Duration : 12 days
Where : Grenada, Caribbean
Caribbean Christmas Sailing; Barbados to Martinique
Join classic wooden windjammer Florette for a Caribbean sailing adventure from Barbados to Martinique.
Date : 22 December 2023
Vessel : Florette
Duration : 12 days
Where : Barbados/Martinique
Christmas Sailing in the Caribbean
Leave the stresses of Christmas behind as Eye of the Wind sails you from Barbados to Grenada.
Date : 22 December 2023
Vessel : Eye of the Wind
Duration : 8 days
Where : Barbados/Grenada
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 : 27 December 2023
Vessel : Chronos
Duration : 8 days
Where : St Lucia, Caribbean
New Year Sailing in the Caribbean
Enjoy luxury Caribbean sailing with classic yacht Rhea as she sails from Antigua to St Martin.
Date : 28 December 2023
Vessel : Rhea
Duration : 10 days
Where : Lesser Antilles, Caribbean
Luxury Caribbean Sailing in the Grenadines
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 3 January 2024
Vessel : Chronos
Duration : 12 days
Where : Grenada, Caribbean
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 5 January 2024
Vessel : Blue Clipper
Duration : 10 days
Where : Grenada, Caribbean
Private Charter in the Caribbean
Take historic tall ship Florette for your very own bespoke private charter adventure in the Caribbean from the island of Martinique.
Date : 5 January 2024
Vessel : Florette
Duration : 8 days
Where : Martinique
Luxury Caribbean Sailing from St Martin to BVI
Explore the culture of the colourful Caribbean islands on luxury yacht Rhea as she journeys from St Martin to Tortola BVI.
Date : 10 January 2024
Vessel : Rhea
Duration : 8 days
Where : St Martin, Caribbean
Caribbean Tall Ship Sailing; Martinique to Grenada
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Martinique to Grenada.
Date : 13 January 2024
Vessel : Florette
Duration : 8 days
Where : Martinique/Grenada
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 16 January 2024
Vessel : Blue Clipper
Duration : 11 days
Where : Grenada, Caribbean
Luxury Caribbean Sailing around BVI
Sail and explore the tropical Caribbean island chain of the British Virgin Islands with luxury yacht Rhea.
Date : 17 January 2024
Vessel : Rhea
Duration : 8 days
Where : BVI, Caribbean
Caribbean Tall Ship Sailing; Grenada & the Grenadines
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Grenada to explore the Grenadines.
Date : 20 January 2024
Vessel : Florette
Duration : 8 days
Where : Grenada
Luxury Caribbean Sailing in the Grenadines
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 21 January 2024
Vessel : Chronos
Duration : 15 days
Where : Grenada, Caribbean
Private Charter in the Caribbean
Take historic tall ship Florette for your very own bespoke private charter adventure in the Caribbean from the island of Grenada.
Date : 27 January 2024
Vessel : Florette
Duration : 8 days
Where : Grenada
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 28 January 2024
Vessel : Blue Clipper
Duration : 8 days
Where : Grenada, Caribbean
Sailing & Whale Watching in the Dominican Republic
Luxury Caribbean sailing and whale watching in the Dominican Republic on yacht Rhea.
Date : 31 January 2024
Vessel : Rhea
Duration : 11 days
Where : Dominican Republic
Luxury Caribbean Sailing in the Grenadines
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 4 February 2024
Vessel : Chronos
Duration : 15 days
Where : Grenada, Caribbean
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 6 February 2024
Vessel : Blue Clipper
Duration : 11 days
Where : Grenada, Caribbean
Sailing & Whale Watching in the Dominican Republic
Luxury Caribbean sailing and whale watching in the Dominican Republic on yacht Rhea.
Date : 10 February 2024
Vessel : Rhea
Duration : 11 days
Where : Dominican Republic
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 18 February 2024
Vessel : Blue Clipper
Duration : 8 days
Where : Grenada, Caribbean
Luxury Caribbean Sailing in the Grenadines
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 18 February 2024
Vessel : Chronos
Duration : 11 days
Where : Grenada, Caribbean
Sailing & Whale Watching in the Dominican Republic
Luxury Caribbean sailing and whale watching in the Dominican Republic on yacht Rhea.
Date : 21 February 2024
Vessel : Rhea
Duration : 11 days
Where : Dominican Republic
Caribbean Tall Ship Sailing; Antigua to St Martin
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Antigua to St Martin.
Date : 24 February 2024
Vessel : Florette
Duration : 8 days
Where : Antigua/St Martin
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 27 February 2024
Vessel : Blue Clipper
Duration : 11 days
Where : Grenada, Caribbean
Luxury Caribbean Sailing in the Grenadines
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 28 February 2024
Vessel : Chronos
Duration : 11 days
Where : Grenada, Caribbean
Caribbean Tall Ship Sailing; St Martin to Antigua
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of St Martin to Antigua.
Date : 2 March 2024
Vessel : Florette
Duration : 8 days
Where : St Martin/Antigua
Caribbean Tall Ship Sailing; Antigua to St Martin
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Antigua to St Martin.
Date : 9 March 2024
Vessel : Florette
Duration : 8 days
Where : Antigua/St Martin
Luxury Caribbean Sailing from 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 Rhea.
Date : 9 March 2024
Vessel : Rhea
Duration : 8 days
Where : Caribbean
Tall Ship Sailing in the Caribbean
Explore the beauty of Caribbean islands Grenada, St Vincents and the Grenadines onboard tall-ship Blue Clipper. No experience needed to climb aboard!
Date : 10 March 2024
Vessel : Blue Clipper
Duration : 8 days
Where : Grenada, Caribbean
Luxury Caribbean Sailing in the Grenadines
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to explore the Grenadines.
Date : 10 March 2024
Vessel : Chronos
Duration : 8 days
Where : Grenada, Caribbean
Luxury Caribbean Sailing around Antigua
Sail with luxury yacht Rhea this Easter as she discovers the Caribbean Leeward islands under sail.
Date : 16 March 2024
Vessel : Rhea
Duration : 12 days
Where : Antigua, Caribbean
Luxury Caribbean Sailing from Grenada to Martinique
Enjoy the beauty of the colourful Caribbean islands with luxury yacht Chronos as she sails from Grenada to Martinique.
Date : 17 March 2024
Vessel : Chronos
Duration : 7 days
Where : Grenada, Caribbean
Offshore Ocean Passage from Grenada to Scotland
Spend 34days at sea with tall ship Blue Clipper as she makes her way across the Atlantic from the Caribbean island of Grenada the West coast of Scotland.
Date : 20 March 2024
Vessel : Blue Clipper
Duration : 34 days
Where : Caribbean/Scotland
Luxury Caribbean Sailing from Martinique to Antigua
Luxury Caribbean sailing with tall ship Chronos from Martinique to Antigua exploring Dominica & Guadeloupe.
Date : 23 March 2024
Vessel : Chronos
Duration : 8 days
Where : Martinique, Caribbean
Luxury Caribbean Sailing around Antigua
Sail with luxury yacht Rhea this Easter as she discovers the Caribbean Leeward islands under sail.
Date : 27 March 2024
Vessel : Rhea
Duration : 11 days
Where : Antigua, Caribbean
Caribbean Tall Ship Sailing; St Martin to Guadeloupe
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of St Martin to Guadeloupe.
Date : 30 March 2024
Vessel : Florette
Duration : 8 days
Where : St Martin/Guadeloupe
Luxury Sailing around Antigua & Barbuda
Explore the Caribbean island of Antigua and Barbuda with luxury classic yacht Chronos.
Date : 30 March 2024
Vessel : Chronos
Duration : 8 days
Where : Antigua, Caribbean
Caribbean Tall Ship Sailing; Guadeloupe to Martinique
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Guadeloupe to Martinique.
Date : 6 April 2024
Vessel : Florette
Duration : 8 days
Where : Guadeloupe/Martinique
Luxury Caribbean Sailing around Antigua
Explore the Caribbean island of Antigua and Barbuda with luxury classic yacht Rhea.
Date : 6 April 2024
Vessel : Rhea
Duration : 8 days
Where : Antigua, Caribbean
Luxury Sailing around Antigua & Barbuda
Explore the Caribbean island of Antigua and Barbuda with luxury classic yacht Chronos.
Date : 6 April 2024
Vessel : Chronos
Duration : 8 days
Where : Antigua, Caribbean
Private Charter in the Caribbean
Take historic tall ship Florette for your very own bespoke private charter adventure in the Caribbean from the island of Martinique.
Date : 13 April 2024
Vessel : Florette
Duration : 8 days
Where : Martinique
Private Charter in the Caribbean
Take historic tall ship Florette for your very own bespoke private charter adventure in the Caribbean from the island of Martinique.
Date : 20 April 2024
Vessel : Florette
Duration : 8 days
Where : Martinique
Offshore Sailing Passage from Antigua to the Azores
Sail from the Caribbean island of Antigua to the Atlantic archipelago of the Azores with luxury yacht Rhea.
Date : 23 April 2024
Vessel : Rhea
Duration : 17 days
Where : Antigua/Azores
Offshore Sailing Passage from Antigua to the Azores
Sail from the Caribbean island of Antigua to the Atlantic archipelago of the Azores with luxury yacht Chronos.
Date : 23 April 2024
Vessel : Chronos
Duration : 17 days
Where : Antigua/Azores
Caribbean Tall Ship Sailing; Martinique to Guadeloupe
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Martinique to Guadeloupe.
Date : 27 April 2024
Vessel : Florette
Duration : 8 days
Where : Martinique/Guadeloupe
Caribbean Tall Ship Sailing; Guadeloupe to St Martin
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of Guadeloupe to St Martin.
Date : 4 May 2024
Vessel : Florette
Duration : 8 days
Where : Guadeloupe/St Martin
Caribbean Tall Ship Sailing; St Martin to British Virgin Islands
Join classic wooden windjammer Florette for a Caribbean sailing adventure from the island of St Martin to the British Virgin Islands (BVI)
Date : 11 May 2024
Vessel : Florette
Duration : 8 days
Where : St Martin/BVI
Caribbean Tall Ship Sailing around the British Virgin Islands
Join classic wooden windjammer Florette for a Caribbean sailing adventure around the British Virgin Islands.
Date : 18 May 2024
Vessel : Florette
Duration : 8 days
Where : British Virgin Islands