Caribbean morning sunlight at Petit Piton, St Lucia, Blue Clipper anchored
Turtle on seabed, Tobago Cays, Caribbean wildlife
Caribbean guests at waterfall of Dark Falls, St Vincent
Blue Clipper tall ship anchored off the coast of Wallilabou, St Vincent, Caribbean
Caribbean Atlantic view beach on island of St Lucia
Beach on Mustique island, Caribbean, St Vincent and the Grenadines

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
Rhea classic yacht sailing underway offshore from bow
At helm of Chronos Rhea SC open ocean
Rhea sailing
Kairos breakfast spread food dining onboard
Crew member on board Chronos Rhea
Tenerife-Las Teresitas-beach

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
i
£6,720.00€7,800.00
Berths available
View Voyage
Offshore Atlantic Yacht Sailing from Cape Verde to Martinique
sailing side shot
Crew member winching sails on board SC Chronos Rhea Kairos
Chronos adventure sailing bow
Santiago Cape Verde
At helm of Chronos Rhea SC open ocean

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
i
£5,990.00€6,900.00
Berths available
View Voyage
Luxury Caribbean Sailing Exploring Antigua & St Barts
Rhea sailing in the Med with Chronos in the background
Guests swimming in the Caribbean Antigua Chronos Rhea
Chronos guests onboard relaxing on deck luxury yacht
Caribbean, view of deserted island in Antigua and Barbuda
Cabin on board Chronos and Rhea Interiors
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests on tender in Caribbean, Chronos Rhea
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
i
£4,450.00€5,250.00
Berths available
View Voyage
Luxury Sailing around St Martin
Kairos in full sail Caribbean homepage
St Martin Caribbean
Kairos yacht on deck in BVIs British Virgin Islands
Caribbean St Martin
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored off the coast of Antigua, Caribbean SC

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
i
£2,775.00€3,150.00
Berths available
View Voyage
Luxury Yacht Sailing in the Grenadines
Skyelark sail
St Lucia Caribbean Marigot bay unsplash
Skyelark Oyster 62 saloon area
St Lucia unsplash Caribbean
Skyelark under sail
Beach on Mustique island, Caribbean, St Vincent and the Grenadines

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
i
£2,950.00€3,687.50
Berths available
View Voyage
Luxury Caribbean Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Guests enjoying meal on board SC Chronos Rhea
Chronos sunny deck onboard underway sailing in Caribbean
View of the beach on Martinique, Caribbean
Aerial View of the island of Guadeloupe
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
i
£3,400.00€3,900.00
Berths available
View Voyage
Luxury Sailing around St Martin
Kairos in full sail Caribbean homepage
St Martin Caribbean
Kairos yacht on deck in BVIs British Virgin Islands
Caribbean St Martin
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored off the coast of Antigua, Caribbean SC

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
i
£3,080.00€3,500.00
Berths available
View Voyage
Luxury Caribbean Sailing Holiday around Antigua
Caribbean Antigua anchorage
Rhea classic yacht under full sail
Guests on tender in Caribbean, Chronos Rhea
Guests swimming in the Caribbean Antigua Chronos Rhea
Couple on board SC yacht watching the sunset Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Caribbean Antigua Unsplash sunset

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
i
£3,305.00€3,750.00
Berths available
View Voyage
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Aerial view of the island of Martinique, Caribbean
Chronos yacht in full sail sunshine sailing SC
Chronos morning guest reading on deck sunshine
Aerial view of Petit Piton, St Lucia, Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Chronos guests on deck tidying ropes onboard
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos

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
i
£3,740.00€4,400.00
Berths available
View Voyage
Luxury Sailing in the British Virgin Islands
Kairos yacht in BVIs caribbean
BVI view overlooking British Virgin Islands, Spanish Town, Virgin Gorda
Guests reading and relaxing on deck of Kairos
Caribbean St Martin
Kairos anchored off the coast of Antigua, Caribbean SC
Kairos yacht underway on deck sailing in the BVIs British Virgin Islands
2027

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
i
£2,830.00€3,150.00
Berths available
View Voyage
Luxury Caribbean Sailing Exploring Antigua & St Barts
Rhea sailing in the Med with Chronos in the background
Guests swimming in the Caribbean Antigua Chronos Rhea
Chronos guests onboard relaxing on deck luxury yacht
Caribbean, view of deserted island in Antigua and Barbuda
Cabin on board Chronos and Rhea Interiors
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests on tender in Caribbean, Chronos Rhea
2027

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
i
£4,440.00€5,050.00
Berths available
View Voyage
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Aerial view of the island of Martinique, Caribbean
Chronos yacht in full sail sunshine sailing SC
Chronos morning guest reading on deck sunshine
Aerial view of Petit Piton, St Lucia, Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Chronos guests on deck tidying ropes onboard
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
i
£4,495.00€5,050.00
Berths available
View Voyage
Luxury Yacht Sailing in the Grenadines
Skyelark sail
St Lucia Caribbean Marigot bay unsplash
Skyelark Oyster 62 saloon area
St Lucia unsplash Caribbean
Skyelark under sail
Beach on Mustique island, Caribbean, St Vincent and the Grenadines
2027

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
i
£3,250.00€4,062.50
Berths available
View Voyage
Luxury Sailing Holiday in the BVI
Kairos in full sail Caribbean homepage
Aerial View of the British Virgin Islands
Kairos yacht on deck in sunny BVIs British Virgin Islands
Kairos anchored with view of tropical Caribbean beach
Guests reading and relaxing on deck of Kairos
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
i
£2,830.00€3,150.00
Berths available
View Voyage
Luxury Caribbean Sailing Cruise from Antigua
Rhea classic yacht under full sail
Aerial View of the island of Guadeloupe
Chronos guests onboard at sunset drinks on deck
View of the beach on Martinique, Caribbean
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
i
£3,790.00€4,300.00
Berths available
View Voyage
Luxury Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests enjoying meal on board SC Chronos Rhea
View of the beach on Martinique, Caribbean
Guests on beach with Chronos in background Caribbean
2027

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
i
£3,395.00€3,800.00
Berths available
View Voyage
Luxury Sailing Holiday in the BVI
Kairos in full sail Caribbean homepage
Aerial View of the British Virgin Islands
Kairos yacht on deck in sunny BVIs British Virgin Islands
Kairos anchored with view of tropical Caribbean beach
Guests reading and relaxing on deck of Kairos
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
i
£2,830.00€3,150.00
Berths available
View Voyage
Luxury Yacht Sailing in the Grenadines
Skyelark sail
St Lucia Caribbean Marigot bay unsplash
Skyelark Oyster 62 saloon area
St Lucia unsplash Caribbean
Skyelark under sail
Beach on Mustique island, Caribbean, St Vincent and the Grenadines
2027

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
i
£3,250.00€4,062.50
Berths available
View Voyage
Caribbean Tall Ship Sailing to Antigua from Guadeloupe
Blue Clipper guest onboard Blue Clipper on bowsprit female sailor
Tall ship Blue Clipper sailing in the sunshine open ocean
Blue Clipper view of Les Saintes Guadeloupe Caribbean
Blue Clipper tall ship guests on deck pulling ropes
Blue Clipper Full sails Hebrides
Dominican Republic Isla saona
2027

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
i
£2,065.00€2,422.50
Berths available
View Voyage
Luxury Caribbean Sailing Exploring Antigua & St Barts
Rhea sailing in the Med with Chronos in the background
Guests swimming in the Caribbean Antigua Chronos Rhea
Chronos guests onboard relaxing on deck luxury yacht
Caribbean, view of deserted island in Antigua and Barbuda
Cabin on board Chronos and Rhea Interiors
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests on tender in Caribbean, Chronos Rhea
2027

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
i
£4,440.00€5,050.00
Berths available
View Voyage
Luxury Sailing Holiday in the BVI
Kairos in full sail Caribbean homepage
Aerial View of the British Virgin Islands
Kairos yacht on deck in sunny BVIs British Virgin Islands
Kairos anchored with view of tropical Caribbean beach
Guests reading and relaxing on deck of Kairos
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
i
£2,830.00€3,150.00
Berths available
View Voyage
Caribbean Sea Adventure: San Blas Islands
Sea Dragon yacht underway heeling sunshine sailing
Aerial view of San Blas Islands, Panama
Sea Dragon guests talking on bowsprit sunshine seas
Colourful Houses in Aruba, Caribbean Sea
Sea Dragon guests on board relaxing in sunshine destination
Sea Dragon yacht underway from port side sailing
2027

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
i
£3,765.00€4,706.25
Berths available
View Voyage
Luxury Sailing Holiday in the BVI
Kairos in full sail Caribbean homepage
Aerial View of the British Virgin Islands
Kairos yacht on deck in sunny BVIs British Virgin Islands
Kairos anchored with view of tropical Caribbean beach
Guests reading and relaxing on deck of Kairos
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
i
£2,830.00€3,150.00
Berths available
View Voyage
Luxury Caribbean Sailing Cruise from Antigua
Rhea classic yacht under full sail
Aerial View of the island of Guadeloupe
Chronos guests onboard at sunset drinks on deck
View of the beach on Martinique, Caribbean
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
i
£4,700.00€5,350.00
Berths available
View Voyage
Luxury Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests enjoying meal on board SC Chronos Rhea
View of the beach on Martinique, Caribbean
Guests on beach with Chronos in background Caribbean
2027

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
i
£3,395.00€3,800.00
Berths available
View Voyage
Luxury Yacht Sailing in the Grenadines
Skyelark sail
St Lucia Caribbean Marigot bay unsplash
Skyelark Oyster 62 saloon area
St Lucia unsplash Caribbean
Skyelark under sail
Beach on Mustique island, Caribbean, St Vincent and the Grenadines
2027

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
i
£3,250.00€4,062.50
Berths available
View Voyage
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Aerial view of the island of Martinique, Caribbean
Chronos yacht in full sail sunshine sailing SC
Chronos morning guest reading on deck sunshine
Aerial view of Petit Piton, St Lucia, Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Chronos guests on deck tidying ropes onboard
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
i
£4,495.00€5,050.00
Berths available
View Voyage
Luxury Caribbean Sailing Exploring Antigua & St Barts
Rhea sailing in the Med with Chronos in the background
Guests swimming in the Caribbean Antigua Chronos Rhea
Chronos guests onboard relaxing on deck luxury yacht
Caribbean, view of deserted island in Antigua and Barbuda
Cabin on board Chronos and Rhea Interiors
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests on tender in Caribbean, Chronos Rhea
2027

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
i
£4,440.00€5,050.00
Berths available
View Voyage
Tall Ship Sailing in Antigua, Caribbean
Blue Clipper tall ship anchored off the coast of Wallilabou, St Vincent, Caribbean
Blue Clipper guest onboard Blue Clipper on bowsprit female sailor
Tall ship Blue Clipper sailing in the sunshine open ocean
Blue Clipper view of Les Saintes Guadeloupe Caribbean
Blue Clipper tall ship guests on deck pulling ropes
Blue Clipper Full sails Hebrides
Guest walking along sandy beach off Carriacou, Grenada, Caribbean
2027

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
i
£2,065.00€2,422.50
Berths available
View Voyage
Luxury Sailing Holiday in the BVI
Kairos in full sail Caribbean homepage
Aerial View of the British Virgin Islands
Kairos yacht on deck in sunny BVIs British Virgin Islands
Kairos anchored with view of tropical Caribbean beach
Guests reading and relaxing on deck of Kairos
Kairos anchored off the coast of Antigua, Caribbean SC
2027
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
i
£2,830.00€3,150.00
Berths available
View Voyage
Luxury Sailing in the Leeward Islands, Caribbean
St Lucia unsplash Caribbean
Skyelark sail
Aerial view of the island of Martinique, Caribbean
Skyelark Oyster 62 saloon area
View of the beach on Martinique, Caribbean
Martinique Caribbean
2027

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
i
£3,250.00€4,062.50
Berths available
View Voyage
Luxury Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests enjoying meal on board SC Chronos Rhea
View of the beach on Martinique, Caribbean
Guests on beach with Chronos in background Caribbean
2027

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
i
£3,395.00€3,800.00
Berths available
View Voyage
Luxury Caribbean Sailing Holiday around Antigua
Caribbean Antigua anchorage
Rhea classic yacht under full sail
Guests on tender in Caribbean, Chronos Rhea
Guests swimming in the Caribbean Antigua Chronos Rhea
Couple on board SC yacht watching the sunset Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Caribbean Antigua Unsplash sunset
2027

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
i
£3,360.00€3,800.00
Berths available
View Voyage
Luxury Sailing Holiday in the BVI
Kairos in full sail Caribbean homepage
Aerial View of the British Virgin Islands
Kairos yacht on deck in sunny BVIs British Virgin Islands
Kairos anchored with view of tropical Caribbean beach
Guests reading and relaxing on deck of Kairos
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
i
£2,830.00€3,150.00
Berths available
View Voyage
Tall Ship Sailing in Antigua, Caribbean
Blue Clipper tall ship anchored off the coast of Wallilabou, St Vincent, Caribbean
Blue Clipper guest onboard Blue Clipper on bowsprit female sailor
Tall ship Blue Clipper sailing in the sunshine open ocean
Blue Clipper view of Les Saintes Guadeloupe Caribbean
Blue Clipper tall ship guests on deck pulling ropes
Blue Clipper Full sails Hebrides
Guest walking along sandy beach off Carriacou, Grenada, Caribbean
2027

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
i
£2,065.00€2,442.50
Berths available
View Voyage
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Aerial view of the island of Martinique, Caribbean
Chronos yacht in full sail sunshine sailing SC
Chronos morning guest reading on deck sunshine
Aerial view of Petit Piton, St Lucia, Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Chronos guests on deck tidying ropes onboard
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
i
£4,495.00€5,050.00
Berths available
View Voyage
Luxury Caribbean Sailing Holiday around Antigua
Caribbean Antigua anchorage
Rhea classic yacht under full sail
Guests on tender in Caribbean, Chronos Rhea
Guests swimming in the Caribbean Antigua Chronos Rhea
Couple on board SC yacht watching the sunset Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Caribbean Antigua Unsplash sunset
2027

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
i
£3,360.00€3,800.00
Berths available
View Voyage
Tall Ship Sailing Across the Atlantic to the UK
Blue Clipper full sails bow scotland
Blue Clipper guests pulling ropes on deck of tall ship
Night Sailing on deck of Blue Clipper
Guest climbing the rigging on Blue Clipper
Blue Clipper tall ship from bowsprit at sunset
2027
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
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Atlantic Expedition Sailing Holiday to the Azores
Blue Clipper full sails bow scotland
Blue Clipper guests on deck at sunset
Blue Clipper guests pulling ropes on deck of tall ship
Blue Clipper view of Admiralty Bay, Bequia, St Vincent
Night Sailing on deck of Blue Clipper
Blue Clipper Guest on deck at sunset at sea passage crossing
2027
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
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Luxury Yacht Sailing Holiday to Antigua
Skyelark sail
Caribbean Antigua anchorage
Skyelark Oyster 62 saloon area
Caribbean island of Antigua, Barbuda beach
Skyelark under sail
View of the beach on Martinique, Caribbean
2027
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
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Luxury Caribbean Sailing St Barths Regatta
Chronos and Rhea sailing in company, St Tropez regatta
Chronos yacht underway on deck sunshine sailing crew
Caribbean, colourful island of St Barths, St Barts, St Bartholemew
Rhea sailing in the Med with Chronos in the background
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
View of Colombier in St Barths, Caribbean
2027
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
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Luxury Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests enjoying meal on board SC Chronos Rhea
View of the beach on Martinique, Caribbean
Guests on beach with Chronos in background Caribbean
2027

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
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Luxury Sailing St Barths Regatta
Kairos and Rhea sailing in company, open ocean
Colombier, St Barths
Kairos on deck with blue sky south Croatia
Kairos anchored off the coast of Antigua, Caribbean SC
Kairos crew member on board
Caribbean St Martin
2027
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
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Luxury Sailing around St Martin
Kairos in full sail Caribbean homepage
St Martin Caribbean
Kairos yacht on deck in BVIs British Virgin Islands
Caribbean St Martin
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
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Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Aerial view of the island of Martinique, Caribbean
Chronos yacht in full sail sunshine sailing SC
Chronos morning guest reading on deck sunshine
Aerial view of Petit Piton, St Lucia, Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Chronos guests on deck tidying ropes onboard
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
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Cross the Atlantic Ocean from The Caribbean
Rhea classic yacht sailing underway offshore from bow
Malta coast
Rhea sailing
Chronos yacht underway on deck sunshine sailing crew
Gibraltar
Rhea bows sailing
2027

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
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Luxury Sailing around St Martin
Kairos in full sail Caribbean homepage
St Martin Caribbean
Kairos yacht on deck in BVIs British Virgin Islands
Caribbean St Martin
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
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Luxury Sailing Holiday in the Caribbean: Martinique to Antigua
Chronos anchored off St Vincents West Coast, Caribbean
Aerial View of the island of Guadeloupe
Chronos yacht underway on deck sunshine sailing crew
Guests swimming in the Caribbean Antigua Chronos Rhea
Chronos in full sail wide background
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
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Offshore Atlantic Yacht Sailing from Antigua to Portugal
sailing side shot
Chronos yacht from bowsprit sunshine sailing
Crew member winching sails on board SC Chronos Rhea Kairos
Gibraltar
deck sail
Chronos adventure sailing bow
Chronos sunny deck onboard underway sailing in Caribbean
2027

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
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Atlantic Crossing Sailing Adventure; Tenerife to Antigua
Rhea classic yacht sailing underway offshore from bow
At helm of Chronos Rhea SC open ocean
Rhea sailing
Kairos breakfast spread food dining onboard
Crew member on board Chronos Rhea
Tenerife-Las Teresitas-beach
2027

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
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Atlantic Sailing from Tenerife to the Caribbean
Kairos in full sail Caribbean homepage
Kairos crew member on board
Caribbean St Martin
Kairos on deck with blue sky south Croatia
St Martin Caribbean
View from mast of Kairos underway
2027

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
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Offshore Atlantic Yacht Sailing from Cape Verde to Martinique
sailing side shot
Crew member winching sails on board SC Chronos Rhea Kairos
Chronos adventure sailing bow
Santiago Cape Verde
At helm of Chronos Rhea SC open ocean
2027

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
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Luxury Caribbean Sailing Holiday around Antigua
Caribbean Antigua anchorage
Rhea classic yacht under full sail
Guests on tender in Caribbean, Chronos Rhea
Guests swimming in the Caribbean Antigua Chronos Rhea
Couple on board SC yacht watching the sunset Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Caribbean Antigua Unsplash sunset
2027

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
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Luxury Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests enjoying meal on board SC Chronos Rhea
View of the beach on Martinique, Caribbean
Guests on beach with Chronos in background Caribbean
2027

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
View Voyage
Luxury Sailing around St Martin
Kairos in full sail Caribbean homepage
St Martin Caribbean
Kairos yacht on deck in BVIs British Virgin Islands
Caribbean St Martin
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
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Luxury Caribbean Sailing Holiday around Antigua
Caribbean Antigua anchorage
Rhea classic yacht under full sail
Guests on tender in Caribbean, Chronos Rhea
Guests swimming in the Caribbean Antigua Chronos Rhea
Couple on board SC yacht watching the sunset Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Caribbean Antigua Unsplash sunset
2027

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
View Voyage
Luxury Caribbean Sailing; Martinique, St Lucia & the Grenadines
Aerial view of the island of Martinique, Caribbean
Chronos yacht in full sail sunshine sailing SC
Chronos morning guest reading on deck sunshine
Aerial view of Petit Piton, St Lucia, Caribbean
Chronos anchored off St Vincents West Coast, Caribbean
Chronos guests on deck tidying ropes onboard
Guests enjoying meal on board SC Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
2027

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
View Voyage
Luxury Sailing around St Martin
Kairos in full sail Caribbean homepage
St Martin Caribbean
Kairos yacht on deck in BVIs British Virgin Islands
Caribbean St Martin
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored off the coast of Antigua, Caribbean SC
2027

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
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Luxury Caribbean Sailing Holiday around Antigua
Caribbean Antigua anchorage
Rhea classic yacht under full sail
Guests on tender in Caribbean, Chronos Rhea
Guests swimming in the Caribbean Antigua Chronos Rhea
Couple on board SC yacht watching the sunset Chronos Rhea
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Caribbean Antigua Unsplash sunset
2027

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
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Luxury Sailing Holiday from Martinique
Chronos in full sail blue sky GF
Martinique Caribbean
SC yacht anchored off Caribbean beach Chronos Rhea Kairos
Guests enjoying meal on board SC Chronos Rhea
View of the beach on Martinique, Caribbean
Guests on beach with Chronos in background Caribbean
2027

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
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