The Caribbean Sailing Schedule

We have found 36 voyages with berths available.

Show prices in Euro

Atlantic Crossing from 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

Offshore Sailing Passage from 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

Atlantic Sailing Adventure 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

Christmas Sailing in the Caribbean

Leave the stresses of Christmas behind as Eye of the Wind sails you from Barbados to Grenada.
  • Date: 20 December 2024
  • Vessel: Eye of the Wind
  • Duration: 8 days
  • Where: Barbados/Grenada
  • Board type: Full Board

Luxury Caribbean Sailing 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 Christmas Sailing in the Caribbean

Enjoy the beauty of the colourful Caribbean islands at Christmas with luxury yacht Chronos as she sails from Grenada to St Lucia.
  • Date: 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

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 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: 5 January 2025
  • Vessel: Chronos
  • Duration: 11 days
  • Where: Grenada, Caribbean
  • Board type: Full Board

Tall Ship Caribbean 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 Sailing from 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

Tall Ship Caribbean Sailing from 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 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 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

Luxury Caribbean Sailing from Martinique

Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Martinique to explore the islands of Dominica & Guadeloupe.
  • Date: 21 January 2025
  • Vessel: Rhea
  • Duration: 8 days
  • Where: Martinique, Caribbean
  • Board type: Full Board

Tall Ship 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

Luxury Caribbean Sailing from 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

Tall Ship 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 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 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

Luxury Caribbean Sailing 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

Luxury Caribbean Sailing from 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 Caribbean Sailing 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

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

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 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 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

Luxury Caribbean Sailing from Grenada to Martinique

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 Caribbean Sailing from Martinique to Antigua

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

Luxury Caribbean Sailing 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 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 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 Christmas Sailing in the Caribbean

Enjoy the beauty of the colourful Caribbean islands at Christmas with luxury yacht Chronos as she sails from Grenada to St Lucia.
  • Date: 21 December 2025
  • Vessel: Chronos
  • Duration: 8 days
  • Where: Grenada, Caribbean
  • Board type: Full Board

Luxury Caribbean Sailing from Martinique

Enjoy Caribbean sailing with luxury yacht Rhea as she sails from Martinique to explore the islands of Dominica & Guadeloupe.
  • Date: 21 December 2025
  • Vessel: Rhea
  • Duration: 8 days
  • Where: Martinique, Caribbean
  • Board type: Full Board

Luxury New Year Sailing in the Caribbean

Bring in the New Year with luxury and Caribbean sunshine with Chronos as she sails from St Lucia to Grenada.
  • Date: 28 December 2025
  • Vessel: Chronos
  • Duration: 8 days
  • Where: St Lucia, Caribbean
  • Board type: Full Board

Luxury Caribbean Sailing from 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
Refine search
Scotland-Kerrera-castle-sailing

Destinations

Our range of vessels enables us to offer several destinations all over the globe. Which adventure will you choose?

View destinations
Bessie-Ellen-Agnes-Sailing

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.

View fleet