Sailing Holidays in the Caribbean
With year-round warm sunshine, an eclectic mix of cultures, astonishingly blue waters and power soft sand, a sailing holiday in the Caribbean has it all.
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
- Date: 5 February 2023
- Vessel: Chronos
- Duration: 15 days
- Where: Grenada, Caribbean
Luxury Yacht Sailing in the Grenadines
- Date: 8 February 2023
- Vessel: Skyelark
- Duration: 10 days
- Where: St Lucia, Caribbean
Tall Ship Sailing in the BVI, Caribbean
- Date: 10 February 2023
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: British Virgin Islands
Tall Ship Sailing in the BVI, Caribbean
- Date: 17 February 2023
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: British Virgin Islands
Luxury Sailing in the Caribbean
- Date: 19 February 2023
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
Luxury Sailing in the Caribbean
- Date: 5 March 2023
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
Offshore Ocean Passage 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
- Date: 12 March 2023
- Vessel: Chronos
- Duration: 7 days
- Where: Martinique, Caribbean
Luxury Sailing around Antigua & Barbuda
- Date: 18 March 2023
- Vessel: Chronos
- Duration: 8 days
- Where: Antigua, Caribbean
Luxury Easter Sailing in the Caribbean
- Date: 5 April 2023
- Vessel: Rhea
- Duration: 10 days
- Where: Antigua, Caribbean
Offshore Sailing Passage from Antigua to Gibraltar
- Date: 6 April 2023
- Vessel: Chronos
- Duration: 23 days
- Where: Antigua/Gibraltar
Offshore Sailing Passage from Antigua to the Azores
- Date: 16 April 2023
- Vessel: Rhea
- Duration: 18 days
- Where: Antigua/Azores
Luxury Yacht Sailing in the Caribbean
- Date: 19 April 2023
- Vessel: Skyelark
- Duration: 10 days
- Where: Caribbean
Offshore Sailing Passage from Gibraltar to Malta
- Date: 27 April 2023
- Vessel: Chronos
- Duration: 7 days
- Where: Gibraltar/Malta
Offshore Ocean Passage from Portugal to Grenada
- Date: 8 November 2023
- Vessel: Blue Clipper
- Duration: 34 days
- Where: Portugal/Caribbean
Offshore Ocean Passage from Tenerife to the Caribbean
- Date: 28 November 2023
- Vessel: Rhea
- Duration: 23 days
- Where: Canaries/Caribbean
Offshore Sailing Passage from Cape Verde to Grenada
- Date: 4 December 2023
- Vessel: Chronos
- Duration: 15 days
- Where: Cape Verde/Caribbean
Luxury Christmas Sailing in the Caribbean
- Date: 20 December 2023
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
Christmas Sailing in the Caribbean
- Date: 21 December 2023
- Vessel: Rhea
- Duration: 8 days
- Where: Lesser Antilles, Caribbean
Christmas & New Year Sailing in the Caribbean
- Date: 22 December 2023
- Vessel: Blue Clipper
- Duration: 12 days
- Where: Grenada, Caribbean
Caribbean Christmas Sailing; Barbados to Martinique
- Date: 22 December 2023
- Vessel: Florette
- Duration: 12 days
- Where: Barbados/Martinique
Christmas Sailing in the Caribbean
- Date: 22 December 2023
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Barbados/Grenada
Luxury New Year Sailing in the Caribbean
- Date: 27 December 2023
- Vessel: Chronos
- Duration: 8 days
- Where: St Lucia, Caribbean
New Year Sailing in the Caribbean
- Date: 28 December 2023
- Vessel: Rhea
- Duration: 10 days
- Where: Lesser Antilles, Caribbean
Luxury Caribbean Sailing in the Grenadines
- Date: 3 January 2024
- Vessel: Chronos
- Duration: 12 days
- Where: Grenada, Caribbean
Tall Ship Sailing in the Caribbean
- Date: 5 January 2024
- Vessel: Blue Clipper
- Duration: 10 days
- Where: Grenada, Caribbean
Private Charter in the Caribbean
- Date: 5 January 2024
- Vessel: Florette
- Duration: 8 days
- Where: Martinique
Luxury Caribbean Sailing from St Martin to BVI
- Date: 10 January 2024
- Vessel: Rhea
- Duration: 8 days
- Where: St Martin, Caribbean
Caribbean Tall Ship Sailing; Martinique to Grenada
- Date: 13 January 2024
- Vessel: Florette
- Duration: 8 days
- Where: Martinique/Grenada
Tall Ship Sailing in the Caribbean
- Date: 16 January 2024
- Vessel: Blue Clipper
- Duration: 11 days
- Where: Grenada, Caribbean
Luxury Caribbean Sailing around BVI
- Date: 17 January 2024
- Vessel: Rhea
- Duration: 8 days
- Where: BVI, Caribbean
Caribbean Tall Ship Sailing; Grenada & the Grenadines
- Date: 20 January 2024
- Vessel: Florette
- Duration: 8 days
- Where: Grenada
Luxury Caribbean Sailing in the Grenadines
- Date: 21 January 2024
- Vessel: Chronos
- Duration: 15 days
- Where: Grenada, Caribbean
Private Charter in the Caribbean
- Date: 27 January 2024
- Vessel: Florette
- Duration: 8 days
- Where: Grenada
Tall Ship Sailing in the Caribbean
- Date: 28 January 2024
- Vessel: Blue Clipper
- Duration: 8 days
- Where: Grenada, Caribbean
Sailing & Whale Watching in the Dominican Republic
- Date: 31 January 2024
- Vessel: Rhea
- Duration: 11 days
- Where: Dominican Republic
Luxury Caribbean Sailing in the Grenadines
- Date: 4 February 2024
- Vessel: Chronos
- Duration: 15 days
- Where: Grenada, Caribbean
Tall Ship Sailing in the Caribbean
- Date: 6 February 2024
- Vessel: Blue Clipper
- Duration: 11 days
- Where: Grenada, Caribbean
Sailing & Whale Watching in the Dominican Republic
- Date: 10 February 2024
- Vessel: Rhea
- Duration: 11 days
- Where: Dominican Republic
Tall Ship Sailing in the Caribbean
- Date: 18 February 2024
- Vessel: Blue Clipper
- Duration: 8 days
- Where: Grenada, Caribbean
Luxury Caribbean Sailing in the Grenadines
- Date: 18 February 2024
- Vessel: Chronos
- Duration: 11 days
- Where: Grenada, Caribbean
Sailing & Whale Watching in the Dominican Republic
- Date: 21 February 2024
- Vessel: Rhea
- Duration: 11 days
- Where: Dominican Republic
Caribbean Tall Ship Sailing; Antigua to St Martin
- Date: 24 February 2024
- Vessel: Florette
- Duration: 8 days
- Where: Antigua/St Martin
Tall Ship Sailing in the Caribbean
- Date: 27 February 2024
- Vessel: Blue Clipper
- Duration: 11 days
- Where: Grenada, Caribbean
Luxury Caribbean Sailing in the Grenadines
- Date: 28 February 2024
- Vessel: Chronos
- Duration: 11 days
- Where: Grenada, Caribbean
Caribbean Tall Ship Sailing; 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
- Date: 9 March 2024
- Vessel: Florette
- Duration: 8 days
- Where: Antigua/St Martin
Luxury Caribbean Sailing from St Martin to Antigua
- Date: 9 March 2024
- Vessel: Rhea
- Duration: 8 days
- Where: Caribbean
Tall Ship Sailing in the Caribbean
- Date: 10 March 2024
- Vessel: Blue Clipper
- Duration: 8 days
- Where: Grenada, Caribbean
Luxury Caribbean Sailing in the Grenadines
- Date: 10 March 2024
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
Luxury Caribbean Sailing around Antigua
- Date: 16 March 2024
- Vessel: Rhea
- Duration: 12 days
- Where: Antigua, Caribbean
Luxury Caribbean Sailing from Grenada to Martinique
- Date: 17 March 2024
- Vessel: Chronos
- Duration: 7 days
- Where: Grenada, Caribbean
Offshore Ocean Passage from Grenada to Scotland
- Date: 20 March 2024
- Vessel: Blue Clipper
- Duration: 34 days
- Where: Caribbean/Scotland
Luxury Caribbean Sailing from Martinique to Antigua
- Date: 23 March 2024
- Vessel: Chronos
- Duration: 8 days
- Where: Martinique, Caribbean
Luxury Caribbean Sailing around Antigua
- Date: 27 March 2024
- Vessel: Rhea
- Duration: 11 days
- Where: Antigua, Caribbean
Caribbean Tall Ship Sailing; St Martin to Guadeloupe
- Date: 30 March 2024
- Vessel: Florette
- Duration: 8 days
- Where: St Martin/Guadeloupe
Luxury Sailing around Antigua & Barbuda
- Date: 30 March 2024
- Vessel: Chronos
- Duration: 8 days
- Where: Antigua, Caribbean
Caribbean Tall Ship Sailing; Guadeloupe to Martinique
- Date: 6 April 2024
- Vessel: Florette
- Duration: 8 days
- Where: Guadeloupe/Martinique
Luxury Caribbean Sailing around Antigua
- Date: 6 April 2024
- Vessel: Rhea
- Duration: 8 days
- Where: Antigua, Caribbean
Luxury Sailing around Antigua & Barbuda
- Date: 6 April 2024
- Vessel: Chronos
- Duration: 8 days
- Where: Antigua, Caribbean
Private Charter in the Caribbean
- Date: 13 April 2024
- Vessel: Florette
- Duration: 8 days
- Where: Martinique
Private Charter in the Caribbean
- Date: 20 April 2024
- Vessel: Florette
- Duration: 8 days
- Where: Martinique
Offshore Sailing Passage from Antigua to the Azores
- Date: 23 April 2024
- Vessel: Rhea
- Duration: 17 days
- Where: Antigua/Azores
Offshore Sailing Passage from Antigua to the Azores
- Date: 23 April 2024
- Vessel: Chronos
- Duration: 17 days
- Where: Antigua/Azores
Caribbean Tall Ship Sailing; Martinique to Guadeloupe
- Date: 27 April 2024
- Vessel: Florette
- Duration: 8 days
- Where: Martinique/Guadeloupe
Caribbean Tall Ship Sailing; 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
- Date: 11 May 2024
- Vessel: Florette
- Duration: 8 days
- Where: St Martin/BVI
Caribbean Tall Ship Sailing around the British Virgin Islands
- Date: 18 May 2024
- Vessel: Florette
- Duration: 8 days
- Where: British Virgin Islands
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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