The Caribbean Sailing Schedule
We have found 51 voyages with berths available.
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Offshore Atlantic Crossing from Portugal to Barbados – Leg 1 & 2
Sail the Atlantic with traditional tall ship Blue Clipper as she sails from Portugal to the Caribbean island of Barbados.
- Date: 4 November 2024
- Vessel: Blue Clipper
- Duration: 40 days
- Where: Portugal/Barbados
- Board type: Full Board
Tall Ship Atlantic Crossing Adventure from Tenerife to Barbados
Immerse yourself into life at sea for an Atlantic crossing on traditional tall ship Blue Clipper as she sails from Tenerife to Barbados.
- Date: 17 November 2024
- Vessel: Blue Clipper
- Duration: 30 days
- Where: Tenerife/Barbados
- Board type: Full Board
Atlantic Crossing from Tenerife to Barbados & Christmas in St Lucia
Immerse yourself into life at sea for an Atlantic crossing on the traditional tall ship Blue Clipper as she sails from Tenerife to Barbados and across to St Lucia for Christmas.
- Date: 17 November 2024
- Vessel: Blue Clipper
- Duration: 41 days
- Where: Tenerife/St Lucia
- Board type: Full Board
Sail Across the Atlantic, Tenerife to Barbados
Immerse yourself into life at sea with an expedition sailing adventure on tall ship Eye of the Wind from Tenerife to Barbados.
- Date: 19 November 2024
- Vessel: Eye of the Wind
- Duration: 31 days
- Where: Tenerife/Barbados
- Board type: Full Board
Atlantic Crossing Sailing Adventure; Tenerife to Martinique
Cross the Atlantic Ocean with a sailing adventure onboard luxury yacht Rhea from Tenerife to the Caribbean island of Martinique.
- Date: 28 November 2024
- Vessel: Rhea
- Duration: 23 days
- Where: Tenerife/Caribbean
- Board type: Full Board
Offshore Atlantic Yacht Sailing from Cape Verde to Grenada
Cross the Atlantic Ocean from Cape Verde to the Caribbean island of Grenada for an epic offshore adventure with luxury yacht Chronos.
- Date: 4 December 2024
- Vessel: Chronos
- Duration: 17 days
- Where: Cape Verde/Caribbean
- Board type: Full Board
Caribbean Christmas Onboard a Tall Ship: Barbados to St Lucia
Join tall ship Blue Clipper for a Caribbean Christmas as she sails from Barbados to the island of St Lucia.
- Date: 20 December 2024
- Vessel: Blue Clipper
- Duration: 8 days
- Where: Barbados/St Lucia
- Board type: Full Board
Atlantic Crossing from the Canary Islands to the Caribbean
Experience an Atlantic crossing sailing adventure from the Canary Islands to the Caribbean on traditional lugger Grayhound.
- Date: 20 December 2024
- Vessel: Grayhound
- Duration: 29 days
- Where: Atlantic Crossing
- Board type: Full Board
Luxury Caribbean Sailing Cruise from Martinique
Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Martinique to explore the islands of Dominica & Guadeloupe.
- Date: 21 December 2024
- Vessel: Rhea
- Duration: 8 days
- Where: Martinique, Caribbean
- Board type: Full Board
Luxury Caribbean Christmas: Grenada to St Lucia
Enjoy the beauty of the colourful Caribbean islands at Christmas with luxury yacht Chronos as she sails from Grenada to St Lucia.
- Date: 22 December 2024
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
- Board type: Full Board
New Year Caribbean Sailing from Grenada to Tobago
Set sail from the Caribbean island of Grenada to Tobago with tall ship Eye of the Wind to bring the New Year in style.
- Date: 27 December 2024
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Caribbean
- Board type: Full Board
Caribbean Sunshine Sailing in St Lucia & Grenadines
Sail with tall ship Blue Clipper as she enjoys Caribbean island hopping from St Lucia, exploring the turquoise waters of St Vincent and the Grenadines.
- Date: 28 December 2024
- Vessel: Blue Clipper
- Duration: 8 days
- Where: St Lucia, Caribbean
- Board type: Full Board
Tall Ship Caribbean Sailing from Tobago to Grenada
Set sail from the Caribbean island of Tobago to Grenada with tall ship Eye of the Wind to bring the New Year in style.
- Date: 3 January 2025
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Caribbean
- Board type: Full Board
Luxury Classic Yacht Island Hopping in the Grenadines
As featured in The Sunday Times as the most low-carbon way to explore the Caribbean with a touch of luxury. Sail from Grenada with modern classic yacht Chronos to discover the paradisal beauty of the Grenadines.
- Date: 5 January 2025
- Vessel: Chronos
- Duration: 11 days
- Where: Grenada, Caribbean
- Board type: Full Board
Caribbean Brigantine Sailing from Grenada to St Lucia
Join tall ship Eye of the Wind as she sails from Grenada to St Lucia, exploring the turquoise waters of the Caribbean Sea.
- Date: 10 January 2025
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Caribbean
- Board type: Full Board
Luxury Caribbean Island Explorer: Sailing Martinique to the Grenadines
Enjoy Caribbean sailing at its finest as you explore the Grenadines and St Lucia from Martinique with luxury yacht Rhea.
- Date: 11 January 2025
- Vessel: Rhea
- Duration: 11 days
- Where: Martinique, Caribbean
- Board type: Full Board
Caribbean Sailing Adventure: St Lucia to Martinique
Join tall ship Eye of the Wind as she sails from St Lucia to Martinique, exploring the turquoise waters of the Caribbean Sea.
- Date: 17 January 2025
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Caribbean
- Board type: Full Board
Luxury Sailing & Exploring Grenada, St Vincent and the Grenadines
As featured in The Sunday Times as the most low-carbon way to explore the Caribbean with a touch of luxury. Sail from Grenada with the modern classic yacht Chronos to discover the paradisal beauty of St Lucia, St Vincent and the Grenadines.
- Date: 19 January 2025
- Vessel: Chronos
- Duration: 15 days
- Where: Grenada, Caribbean
- Board type: Full Board
Heritage Caribbean Sailing from Martinique
Join tall ship Eye of the Wind as she sails from Martinique, exploring the turquoise waters of the Caribbean Sea.
- Date: 24 January 2025
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Martinique, Caribbean
- Board type: Full Board
Caribbean Sunshine Sailing in St Lucia & Grenadines
Sail with tall ship Blue Clipper as she enjoys Caribbean island hopping from St Lucia, exploring the turquoise waters of St Vincent and the Grenadines.
- Date: 25 January 2025
- Vessel: Blue Clipper
- Duration: 8 days
- Where: St Lucia, Caribbean
- Board type: Full Board
Sailing the Caribbean island of Tobago with Grayhound
Sail, hike and explore the Caribbean island of Tobago with traditional wooden boat, Grayhound.
- Date: 27 January 2025
- Vessel: Grayhound
- Duration: 7 days
- Where: Tobago, Caribbean
- Board type: Full Board
Luxury Caribbean Island Explorer: Sailing Martinique to the Grenadines
Enjoy Caribbean sailing at its finest as you explore the Grenadines and St Lucia from Martinique with luxury yacht Rhea.
- Date: 29 January 2025
- Vessel: Rhea
- Duration: 11 days
- Where: Martinique, Caribbean
- Board type: Full Board
Brigantine Caribbean Sailing from Martinique to Guadeloupe
Join tall ship Eye of the Wind as she sails from Martinique to Guadeloupe, exploring the turquoise waters of the Caribbean Sea.
- Date: 31 January 2025
- Vessel: Eye of the Wind
- Duration: 8 days
- Where: Caribbean
- Board type: Full Board
Luxury Sailing & Exploring Grenada, St Vincent and the Grenadines
As featured in The Sunday Times as the most low-carbon way to explore the Caribbean with a touch of luxury. Sail from Grenada with the modern classic yacht Chronos to discover the paradisal beauty of St Lucia, St Vincent and the Grenadines.
- Date: 2 February 2025
- Vessel: Chronos
- Duration: 15 days
- Where: Grenada, Caribbean
- Board type: Full Board
Tall Ship Caribbean Explorer St Lucia to Antigua
Sail with the tall ship Blue Clipper as she enjoys Caribbean island hopping from St Lucia to Antigua, exploring the islands of Martinique and Guadeloupe along the way.
- Date: 3 February 2025
- Vessel: Blue Clipper
- Duration: 8 days
- Where: Caribbean
- Board type: Full Board
Sailing in the Caribbean from Tobago to St Vincent
Sail the Caribbean Islands from Tobago to St Vincent, exploring Grenada and the Grenadines along way.
- Date: 6 February 2025
- Vessel: Grayhound
- Duration: 8 days
- Where: The Caribbean
- Board type: Full Board
Luxury Caribbean Sailing Cruise from Martinique
Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Martinique to explore the islands of Dominica & Guadeloupe.
- Date: 8 February 2025
- Vessel: Rhea
- Duration: 8 days
- Where: Martinique, Caribbean
- Board type: Full Board
Offshore Atlantic Crossing from Antigua to Portugal – Leg 1 & 2
Sail the Atlantic Ocean with traditional tall ship Blue Clipper as she sails from the Caribbean island of Antigua to Portugal.
- Date: 15 February 2025
- Vessel: Blue Clipper
- Duration: 41 days
- Where: Antigua/Portugal
- Board type: Full Board
Offshore Atlantic Crossing from Antigua to the Azores – Leg 1
Sail the Atlantic Ocean with traditional tall ship Blue Clipper as she sails from the Caribbean island of Antigua to the Azores.
- Date: 15 February 2025
- Vessel: Blue Clipper
- Duration: 28 days
- Where: Antigua/Azores
- Board type: Full Board
Luxury Caribbean Island Explorer: Sailing Martinique to the Grenadines
Enjoy Caribbean sailing at its finest as you explore the Grenadines and St Lucia from Martinique with luxury yacht Rhea.
- Date: 15 February 2025
- Vessel: Rhea
- Duration: 11 days
- Where: Martinique, Caribbean
- Board type: Full Board
Luxury Classic Yacht Island Hopping in the Grenadines
As featured in The Sunday Times as the most low-carbon way to explore the Caribbean with a touch of luxury. Sail from Grenada with modern classic yacht Chronos to discover the paradisal beauty of the Grenadines.
- Date: 16 February 2025
- Vessel: Chronos
- Duration: 11 days
- Where: Grenada, Caribbean
- Board type: Full Board
Sailing the Grenadines from St Vincent to St Lucia
Discover the Caribbean islands of St Vincent and the Grenadines as you sail with traditional boat Grayhound to St Lucia.
- Date: 17 February 2025
- Vessel: Grayhound
- Duration: 8 days
- Where: The Caribbean
- Board type: Full Board
Caribbean Expedition Sailing from St Martin to Bermuda
Sail with historic tall ship Eye of the Wind as she crosses the Caribbean Ocean from St Martin to Bermuda.
- Date: 18 February 2025
- Vessel: Eye of the Wind
- Duration: 12 days
- Where: The Caribbean
- Board type: Full Board
Luxury Yacht Sailing in the Caribbean from Martinique to St Martin
Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Martinique to St Martin, exploring the islands of Guadeloupe, Montserrat and Antigua.
- Date: 25 February 2025
- Vessel: Rhea
- Duration: 12 days
- Where: Caribbean
- Board type: Full Board
Luxury Classic Yacht Island Hopping in the Grenadines
As featured in The Sunday Times as the most low-carbon way to explore the Caribbean with a touch of luxury. Sail from Grenada with modern classic yacht Chronos to discover the paradisal beauty of the Grenadines.
- Date: 27 February 2025
- Vessel: Chronos
- Duration: 11 days
- Where: Grenada, Caribbean
- Board type: Full Board
Historic Ship 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: 2 March 2025
- Vessel: Eye of the Wind
- Duration: 21 days
- Where: Bermuda/Azores
- Board type: Full Board
Sailing Adventure in the Caribbean with Grayhound
Explore the Caribbean islands from St Lucia to Guadeloupe with traditional wooden lugger Grayhound.
- Date: 3 March 2025
- Vessel: Grayhound
- Duration: 8 days
- Where: St Lucia, Caribbean
- Board type: Full Board
Caribbean Sailing St Martin to Antigua & St Barths Regatta
Join luxury yacht Rhea for smooth Caribbean cruising from St Martin to Antigua, exploring the island of St Barths and the annual Bucket Race regatta along the way.
- Date: 8 March 2025
- Vessel: Rhea
- Duration: 9 days
- Where: Caribbean
- Board type: Full Board
Tropical Island Escape: Luxury Caribbean Sailing in the Grenadines
As featured in The Sunday Times as the most low-carbon way to explore the Caribbean with a touch of luxury. Sail from Grenada with modern classic yacht Chronos to discover the paradisal beauty of the Grenadines.
- Date: 9 March 2025
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
- Board type: Full Board
Luxury Caribbean Sailing Exploring Antigua, St Barts & Montserrat
Enjoy Caribbean island hopping with luxury yacht Rhea as she sails from Antigua exploring Saba, St Barts & Montserrat along the way.
- Date: 16 March 2025
- Vessel: Rhea
- Duration: 10 days
- Where: Caribbean
- Board type: Full Board
Atlantic Crossing from the Caribbean to the Azores
Experience an Atlantic crossing sailing adventure from the Caribbean to the Azores on lugger Grayhound!
- Date: 18 March 2025
- Vessel: Grayhound
- Duration: 25 days
- Where: Atlantic Crossing
- Board type: Full Board
Caribbean Island Hopping and Luxury Sailing
Set sail with luxury yacht Chronos as she island-hops her way from Grenada, through the Grenadines, St Lucia and on to Martinique.
- Date: 23 March 2025
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
- Board type: Full Board
Luxury Sailing Holiday in the Caribbean Islands
Enjoy Caribbean sailing with luxury yacht Chronos as she sails from Martinique to Antigua exploring Dominica & Guadeloupe along the way.
- Date: 30 March 2025
- Vessel: Chronos
- Duration: 8 days
- Where: Martinique, Caribbean
- Board type: Full Board
Deluxe Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
- Date: 5 April 2025
- Vessel: Rhea
- Duration: 8 days
- Where: Antigua, Caribbean
- Board type: Full Board
Offshore Atlantic Yacht Sailing 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: 7 April 2025
- Vessel: Chronos
- Duration: 25 days
- Where: Antigua/Gibraltar
- Board type: Full Board
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 2025
- Vessel: Rhea
- Duration: 17 days
- Where: Antigua/Azores
- Board type: Full Board
Atlantic Crossing Sailing Adventure; Tenerife to Martinique
Cross the Atlantic Ocean with a sailing adventure onboard luxury yacht Rhea from Tenerife to the Caribbean island of Martinique.
- Date: 29 November 2025
- Vessel: Rhea
- Duration: 22 days
- Where: Tenerife/Caribbean
- Board type: Full Board
Offshore Atlantic Yacht Sailing from Cape Verde to Grenada
Cross the Atlantic Ocean from Cape Verde to the Caribbean island of Grenada for an epic offshore adventure with luxury yacht Chronos.
- Date: 4 December 2025
- Vessel: Chronos
- Duration: 17 days
- Where: Cape Verde/Caribbean
- Board type: Full Board
Luxury Caribbean Christmas: Grenada to St Lucia
Enjoy the beauty of the colourful Caribbean islands at Christmas with luxury yacht Chronos as she sails from Grenada to St Lucia.
- Date: 21 December 2025
- Vessel: Chronos
- Duration: 8 days
- Where: Grenada, Caribbean
- Board type: Full Board
Luxury Caribbean Island Explorer: Sailing Martinique to the Grenadines
Enjoy Caribbean sailing at its finest as you explore the Grenadines and St Lucia from Martinique with luxury yacht Rhea.
- Date: 28 December 2025
- Vessel: Rhea
- Duration: 9 days
- Where: Martinique, Caribbean
- Board type: Full Board
New Year Caribbean Celebrations Onboard a Luxury Yacht
Bring in the New Year with luxury and Caribbean sunshine with Chronos as she sails from St Lucia to Grenada.
- Date: 28 December 2025
- Vessel: Chronos
- Duration: 8 days
- Where: St Lucia, Caribbean
- Board type: Full Board
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Our range of vessels enables us to offer several destinations all over the globe. Which adventure will you choose?
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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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