All Caribbean Sailing Holidays
Sailing in the Caribbean is all about island-hopping between quiet anchorages, small coastal communities, and clear, sheltered waters. Swim with turtles, snorkel straight from the boat, and step ashore for local food and laid-back island life. With steady trade winds and warm weather, it’s easy, relaxed sailing throughout the season.
Find out more about sailing holidays in the Caribbean
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We have found 60 voyages with berths available.
Atlantic Crossing Sailing Adventure; Tenerife to Antigua
Cross the Atlantic Ocean with a sailing adventure onboard luxury yacht Rhea from Tenerife to the Caribbean island of Antigua.
Date: 24 Nov 2026
Duration: 23 days
Vessel: Rhea
Where: Tenerife/Caribbean
Board: Full Board
Group Size: 26
Activity: Level 3
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£6,720.00€7,800.00
Berths available
Offshore Atlantic Yacht Sailing from Cape Verde to Martinique
Cross the Atlantic Ocean from Cape Verde to the Caribbean island of Martinique for an epic offshore adventure with classic yacht Chronos.
Date: 5 Dec 2026
Duration: 17 days
Vessel: Chronos
Where: Cape Verde/Caribbean
Board: Full Board
Group Size: 26
Activity: Level 3
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£5,990.00€6,900.00
Berths available
REDUCED SOLO OCCUPANCY
Luxury Caribbean Sailing Exploring Antigua & St Barts
Enjoy Caribbean island hopping with luxury yacht Rhea as she sails from Antigua, exploring Saba & St Barts along the way.
Date: 18 Dec 2026
Duration: 11 days
Vessel: Rhea
Where: Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,450.00€5,250.00
Berths available
Luxury Sailing around St Martin
Join modern yacht Kairos for smooth Caribbean cruising from St Martin, exploring Saba and Anguilla along the way.
Date: 20 Dec 2026
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,775.00€3,150.00
Berths available
Luxury Yacht Sailing in the Grenadines
Discover the Caribbean islands of the Grenadines under sail with luxury sailing yacht, Skyelark.
Date: 22 Dec 2026
Duration: 11 days
Vessel: Skyelark
Where: St Lucia, Caribbean
Board: Full Board
Group Size: 8
Activity: Level 1
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£2,950.00€3,687.50
Berths available
REDUCED SOLO OCCUPANCY
Luxury Caribbean Sailing Holiday from Martinique
Sail modern classic yacht Chronos through the Caribbean from Martinique to Guadeloupe, Dominica and the Îles des Saintes.
Date: 22 Dec 2026
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,400.00€3,900.00
Berths available
Luxury Sailing around St Martin
Join modern yacht Kairos for smooth Caribbean cruising from St Martin, exploring Saba and Anguilla along the way.
Date: 27 Dec 2026
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£3,080.00€3,500.00
Berths available
Luxury Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
Date: 29 Dec 2026
Duration: 8 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,305.00€3,750.00
Berths available
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Experience the finest Caribbean sailing as you explore the Grenadines and St. Lucia from Martinique aboard modern yacht Chronos.
Date: 29 Dec 2026
Duration: 9 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,740.00€4,400.00
Berths available
Luxury Sailing in the British Virgin Islands
Sail the Caribbean islands of St Martin and Anguilla before exploring the British Virgin Islands with modern yacht Kairos.
Date: 9 Jan 2027
Duration: 8 days
Vessel: Kairós
Where: The Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Caribbean Sailing Exploring Antigua & St Barts
Enjoy Caribbean island hopping with luxury yacht Rhea as she sails from Antigua, exploring Saba & St Barts along the way.
Date: 9 Jan 2027
Duration: 11 days
Vessel: Rhea
Where: Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,440.00€5,050.00
Berths available
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Experience the finest Caribbean sailing as you explore the Grenadines and St. Lucia from Martinique aboard modern yacht Chronos.
Date: 9 Jan 2027
Duration: 11 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,495.00€5,050.00
Berths available
Luxury Yacht Sailing in the Grenadines
Discover the Caribbean islands of the Grenadines under sail with luxury sailing yacht, Skyelark.
Date: 11 Jan 2027
Duration: 10 days
Vessel: Skyelark
Where: St Lucia, Caribbean
Board: Full Board
Group Size: 8
Activity: Level 1
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£3,250.00€4,062.50
Berths available
Luxury Sailing Holiday in the BVI
Discover the British Virgin Islands under sail with modern yacht Kairos as she explores the quieter side of island life
Date: 16 Jan 2027
Duration: 8 days
Vessel: Kairós
Where: BVI, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Caribbean Sailing Cruise from Antigua
Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Antigua to explore the islands of Montserrat & Guadeloupe.
Date: 19 Jan 2027
Duration: 9 days
Vessel: Rhea
Where: Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,790.00€4,300.00
Berths available
Luxury Sailing Holiday from Martinique
Experience holiday sailing from Martinique aboard yacht Chronos, discovering Dominica and the beautiful, unhurried Îles des Saintes.
Date: 19 Jan 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,395.00€3,800.00
Berths available
Luxury Sailing Holiday in the BVI
Discover the British Virgin Islands under sail with modern yacht Kairos as she explores the quieter side of island life
Date: 23 Jan 2027
Duration: 8 days
Vessel: Kairós
Where: BVI, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Yacht Sailing in the Grenadines
Discover the Caribbean islands of the Grenadines under sail with luxury sailing yacht, Skyelark.
Date: 25 Jan 2027
Duration: 10 days
Vessel: Skyelark
Where: St Lucia, Caribbean
Board: Full Board
Group Size: 8
Activity: Level 1
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£3,250.00€4,062.50
Berths available
Caribbean Tall Ship Sailing to Antigua from Guadeloupe
Sailing to Antigua aboard tall ship Blue Clipper, through the Windward Islands, with Guadeloupe, Dominica and warm Caribbean waters along the way.
Date: 27 Jan 2027
Duration: 8 days
Vessel: Blue Clipper
Where: Caribbean
Board: Full Board
Group Size: 12
Activity: Level 1
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£2,065.00€2,422.50
Berths available
Luxury Caribbean Sailing Exploring Antigua & St Barts
Enjoy Caribbean island hopping with luxury yacht Rhea as she sails from Antigua, exploring Saba & St Barts along the way.
Date: 27 Jan 2027
Duration: 11 days
Vessel: Rhea
Where: Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,440.00€5,050.00
Berths available
Luxury Sailing Holiday in the BVI
Discover the British Virgin Islands under sail with modern yacht Kairos as she explores the quieter side of island life
Date: 30 Jan 2027
Duration: 8 days
Vessel: Kairós
Where: BVI, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Caribbean Sea Adventure: San Blas Islands
Sail the San Blas Islands aboard Sea Dragon, an ocean-rated expedition yacht, from Aruba to Colon, Panama.
Date: 31 Jan 2027
Duration: 9 days
Vessel: Sea Dragon
Where: Caribbean / Central America
Board: Full Board
Group Size: 12
Activity: Level 4
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£3,765.00€4,706.25
Berths available
Luxury Sailing Holiday in the BVI
Discover the British Virgin Islands under sail with modern yacht Kairos as she explores the quieter side of island life
Date: 6 Feb 2027
Duration: 8 days
Vessel: Kairós
Where: BVI, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Caribbean Sailing Cruise from Antigua
Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Antigua to explore the islands of Montserrat & Guadeloupe.
Date: 6 Feb 2027
Duration: 12 days
Vessel: Rhea
Where: Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,700.00€5,350.00
Berths available
Luxury Sailing Holiday from Martinique
Experience holiday sailing from Martinique aboard yacht Chronos, discovering Dominica and the beautiful, unhurried Îles des Saintes.
Date: 6 Feb 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,395.00€3,800.00
Berths available
Luxury Yacht Sailing in the Grenadines
Discover the Caribbean islands of the Grenadines under sail with luxury sailing yacht, Skyelark.
Date: 8 Feb 2027
Duration: 10 days
Vessel: Skyelark
Where: St Lucia, Caribbean
Board: Full Board
Group Size: 8
Activity: Level 1
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£3,250.00€4,062.50
Berths available
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Experience the finest Caribbean sailing as you explore the Grenadines and St. Lucia from Martinique aboard modern yacht Chronos.
Date: 13 Feb 2027
Duration: 11 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,495.00€5,050.00
Berths available
Luxury Caribbean Sailing Exploring Antigua & St Barts
Enjoy Caribbean island hopping with luxury yacht Rhea as she sails from Antigua, exploring Saba & St Barts along the way.
Date: 17 Feb 2027
Duration: 11 days
Vessel: Rhea
Where: Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,440.00€5,050.00
Berths available
Tall Ship Sailing in Antigua, Caribbean
Sailing in Antigua with tall ship Blue Clipper. Trade winds, turquoise waters, and the Caribbean at its most authentic.
Date: 19 Feb 2027
Duration: 8 days
Vessel: Blue Clipper
Where: Antigua, Caribbean
Board: Full Board
Group Size: 12
Activity: Level 1
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£2,065.00€2,422.50
Berths available
KS200227
Luxury Sailing Holiday in the BVI
Discover the British Virgin Islands under sail with modern yacht Kairos as she explores the quieter side of island life
Date: 20 Feb 2027
Duration: 8 days
Vessel: Kairós
Where: BVI, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Sailing in the Leeward Islands, Caribbean
Explore the Caribbean islands of St Lucia, Martinique and Dominica with luxury sailing yacht Skyelark.
Date: 22 Feb 2027
Duration: 10 days
Vessel: Skyelark
Where: St Lucia, Caribbean
Board: Full Board
Group Size: 8
Activity: Level 1
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£3,250.00€4,062.50
Berths available
Luxury Sailing Holiday from Martinique
Experience holiday sailing from Martinique aboard yacht Chronos, discovering Dominica and the beautiful, unhurried Îles des Saintes.
Date: 23 Feb 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,395.00€3,800.00
Berths available
Luxury Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
Date: 27 Feb 2027
Duration: 8 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,360.00€3,800.00
Berths available
Luxury Sailing Holiday in the BVI
Discover the British Virgin Islands under sail with modern yacht Kairos as she explores the quieter side of island life
Date: 27 Feb 2027
Duration: 7 days
Vessel: Kairós
Where: BVI, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Tall Ship Sailing in Antigua, Caribbean
Sailing in Antigua with tall ship Blue Clipper. Trade winds, turquoise waters, and the Caribbean at its most authentic.
Date: 28 Feb 2027
Duration: 8 days
Vessel: Blue Clipper
Where: Antigua, Caribbean
Board: Full Board
Group Size: 12
Activity: Level 1
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£2,065.00€2,442.50
Berths available
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Experience the finest Caribbean sailing as you explore the Grenadines and St. Lucia from Martinique aboard modern yacht Chronos.
Date: 3 Mar 2027
Duration: 11 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,495.00€5,050.00
Berths available
Luxury Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
Date: 6 Mar 2027
Duration: 8 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,360.00€3,800.00
Berths available
Atlantic Crossing Leg 1 & 2
Tall Ship Sailing Across the Atlantic to the UK
Sail across the Atlantic with tall ship Blue Clipper, from the Caribbean island of Antigua to Penzance, Cornwall.
Date: 9 Mar 2027
Duration: 45 days
Vessel: Blue Clipper
Where: Antigua/UK
Board: Full Board
Group Size: 12
Activity: Level 4
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£6,120.00€7,110.25
Berths available
Atlantic Crossing Leg 1
Atlantic Expedition Sailing Holiday to the Azores
An Atlantic expedition sailing holiday aboard tall ship Blue Clipper, from the Caribbean island of Antigua to the Azores.
Date: 9 Mar 2027
Duration: 32 days
Vessel: Blue Clipper
Where: Antigua/Azores
Board: Full Board
Group Size: 12
Activity: Level 4
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£5,205.00€6,047.75
Berths available
Early bird offer: Until end May 2026
Luxury Yacht Sailing Holiday to Antigua
Sail and explore the Caribbean islands of St Lucia, Guadeloupe, Dominica, Martinique and Antigua with luxury sailing yacht, Skyelark.
Date: 10 Mar 2027
Duration: 10 days
Vessel: Skyelark
Where: Caribbean
Board: Full Board
Group Size: 8
Activity: Level 1
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£3,250.00€4,062.50
Berths available
St Barths Regatta!
Luxury Caribbean Sailing St Barths Regatta
Enjoy Caribbean sailing and island hopping from Antigua as you watch St Barths Bucket Race from luxury yacht Rhea.
Date: 13 Mar 2027
Duration: 11 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
£4,530.00€5,150.00
Berths available
Luxury Sailing Holiday from Martinique
Experience holiday sailing from Martinique aboard yacht Chronos, discovering Dominica and the beautiful, unhurried Îles des Saintes.
Date: 13 Mar 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,395.00€3,800.00
Berths available
St Barths Regatta!
Luxury Sailing St Barths Regatta
Enjoy Caribbean sailing and island hopping from St Martin as you watch St Barths Bucket Race from yacht Kairos.
Date: 13 Mar 2027
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,960.00€3,300.00
Berths available
Luxury Sailing around St Martin
Join modern yacht Kairos for smooth Caribbean cruising from St Martin, exploring Saba and Anguilla along the way.
Date: 20 Mar 2027
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,870.00€3,200.00
Berths available
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Experience the finest Caribbean sailing as you explore the Grenadines and St. Lucia from Martinique aboard modern yacht Chronos.
Date: 20 Mar 2027
Duration: 10 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,185.00€4,700.00
Berths available
Cross the Atlantic Ocean from The Caribbean
Join modern yacht Rhea on a sailing passage, crossing the Atlantic from the Caribbean to Gibraltar
Date: 23 Mar 2027
Duration: 22 days
Vessel: Rhea
Where: Caribeean/Gibraltar
Board: Full Board
Group Size: 26
Activity: Level 3
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£6,050.00€6,900.00
Berths available
Luxury Sailing around St Martin
Join modern yacht Kairos for smooth Caribbean cruising from St Martin, exploring Saba and Anguilla along the way.
Date: 27 Mar 2027
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Sailing Holiday in the Caribbean: Martinique to Antigua
Enjoy a luxury Caribbean sailing holiday aboard Chronos, island-hopping from Martinique to Antigua via Dominica and Guadeloupe.
Date: 29 Mar 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique / Antigua
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,310.00€3,700.00
Berths available
Offshore Atlantic Yacht Sailing from Antigua to Portugal
Cross the Atlantic with yacht Chronos as she sails from the Caribbean island of Antigua to Portimão on the Algarve coast of Portugal.
Date: 6 Apr 2027
Duration: 23 days
Vessel: Chronos
Where: Antigua/Portugal
Board: Full Board
Group Size: 26
Activity: Level 3
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£6,115.00€6,900.00
Berths available
Atlantic Crossing Sailing Adventure; Tenerife to Antigua
Cross the Atlantic Ocean with a sailing adventure onboard luxury yacht Rhea from Tenerife to the Caribbean island of Antigua.
Date: 24 Nov 2027
Duration: 22 days
Vessel: Rhea
Where: Tenerife/Caribbean
Board: Full Board
Group Size: 26
Activity: Level 3
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£6,920.00€7,900.00
Berths available
Atlantic Sailing from Tenerife to the Caribbean
Sail the Atlantic from Tenerife to the Caribbean island of St Martin with modern classic yacht Kairos.
Date: 25 Nov 2027
Duration: 24 days
Vessel: Kairós
Where: The Atlantic
Board: Full Board
Group Size: 16
Activity: Level 2
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£4,455.00€5,000.00
Berths available
Offshore Atlantic Yacht Sailing from Cape Verde to Martinique
Cross the Atlantic Ocean from Cape Verde to the Caribbean island of Martinique for an epic offshore adventure with classic yacht Chronos.
Date: 26 Nov 2027
Duration: 17 days
Vessel: Chronos
Where: Cape Verde/Caribbean
Board: Full Board
Group Size: 26
Activity: Level 3
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£6,310.00€7,100.00
Berths available
Luxury Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
Date: 15 Dec 2027
Duration: 8 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,360.00€3,800.00
Berths available
Luxury Sailing Holiday from Martinique
Experience holiday sailing from Martinique aboard yacht Chronos, discovering Dominica and the beautiful, unhurried Îles des Saintes.
Date: 15 Dec 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,395.00€3,800.00
Berths available
Luxury Sailing around St Martin
Join modern yacht Kairos for smooth Caribbean cruising from St Martin, exploring Saba and Anguilla along the way.
Date: 21 Dec 2027
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£2,830.00€3,150.00
Berths available
Luxury Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
Date: 22 Dec 2027
Duration: 8 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,450.00€3,900.00
Berths available
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Experience the finest Caribbean sailing as you explore the Grenadines and St. Lucia from Martinique aboard modern yacht Chronos.
Date: 22 Dec 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,485.00€3,900.00
Berths available
Luxury Sailing around St Martin
Join modern yacht Kairos for smooth Caribbean cruising from St Martin, exploring Saba and Anguilla along the way.
Date: 28 Dec 2027
Duration: 8 days
Vessel: Kairós
Where: St Martin, Caribbean
Board: Full Board
Group Size: 16
Activity: Level 1
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£3,135.00€3,500.00
Berths available
Luxury Caribbean Sailing Holiday around Antigua
Enjoy Caribbean sailing and island hopping around Antigua and Barbuda with luxury yacht Rhea.
Date: 29 Dec 2027
Duration: 9 days
Vessel: Rhea
Where: Antigua, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£4,440.00€5,050.00
Berths available
Luxury Sailing Holiday from Martinique
Experience holiday sailing from Martinique aboard yacht Chronos, discovering Dominica and the beautiful, unhurried Îles des Saintes.
Date: 29 Dec 2027
Duration: 8 days
Vessel: Chronos
Where: Martinique, Caribbean
Board: Full Board
Group Size: 26
Activity: Level 1
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£3,925.00€4,400.00
Berths available
