Good for

  • Cruising
  • Exploration
  • Ocean passages
  • Training
  • Wildlife
  • Winter sun
  • Sun
  • Racing

Duration

  • 1 day
  • 2 - 6 days
  • 1 week +
  • 2 weeks +

The Caribbean Sailing Schedule

Expedition from Tenerife to the Caribbean

Sail with the crew of Eye of the Wind as they set sail from Tenerife to the island of Saint Martin in the Caribbean.
  • Vessel: Eye of the Wind
  • Where: Tenerife
  • Duration: 29 days
  • Date: 20 November 2019

Expedition from Tenerife to the Caribbean

Sail with the crew of Chronos as they set sail from Tenerife to the island of Martinique in the Caribbean.
  • Vessel: Chronos
  • Where: Tenerife
  • Duration: 23 days
  • Date: 29 November 2019

Ocean Sailing from Portugal to the Caribbean

Cross the Atlantic ocean under sail on tall ship Blue Clipper as she sails from the Algarve to the Caribbean.
  • Vessel: Blue Clipper
  • Where: Atlantic Crossing
  • Duration: 36 days
  • Date: 7 December 2019

Christmas and New Year sailing in the Caribbean

Enjoy the festive season onboard luxury yacht Rhea as she sails and explores the beauty of the colourful Caribbean islands.
  • Vessel: Rhea
  • Where: Caribbean
  • Duration: 16 days
  • Date: 21 December 2019

Christmas sailing in the Caribbean

Enjoy Christmas with a difference onboard luxury yacht Rhea as she sails and explores the beauty of the colourful Caribbean islands.
  • Vessel: Rhea
  • Where: Caribbean
  • Duration: 8 days
  • Date: 21 December 2019

Christmas & New Year in the Caribbean

Expect azure oceans, extraordinary sailing and palm beaches, and throw the stresses of Christmas overboard as you relax into the Caribbean way of life.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 12 days
  • Date: 22 December 2019

Christmas Sailing in the Caribbean

Escape the holiday season madness to sail and explore the culture of the colourful Caribbean islands on Chronos as she sails from Martinique to Antigua.
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 7 days
  • Date: 23 December 2019

Christmas & New Year Sailing in the Caribbean

Escape the holiday season madness to sail and explore the culture of the colourful Caribbean islands on Chronos as she journeys from Martinique to Tortola BVI
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 14 days
  • Date: 23 December 2019

New Year sailing in the Caribbean

Celebrate New Year onboard luxury yacht Rhea as she sails and explores the beauty of the colourful Caribbean islands.
  • Vessel: Rhea
  • Where: Caribbean
  • Duration: 8 days
  • Date: 28 December 2019

New Year Sailing in the Caribbean

Bring the New Year in with style onboard Chronos as she sails colourful Caribbean islands from Antigua to Tortola BVI
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 7 days
  • Date: 30 December 2019

Caribbean Sailing – Pearls of the Lesser Antilles

Enjoy the azure ocean, palm beaches and the incomparable flair of the "Caribbean way of life". What better way to start your New Year?
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 3 January 2020

Expedition from Tenerife to Tobago

A voyage for true sailors! Join the crew of Twister as they set sail for the Caribbean, stopping off at the beautiful Cape Verde islands along the way.
  • Vessel: Twister
  • Where: The Canaries
  • Duration: 32 days
  • Date: 6 January 2020

Caribbean Sailing Tortola BVI to Antigua

Sail and explore the culture of the colourful Caribbean islands on Chronos as she sails from the British Virgin Islands to Antigua.
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 7 days
  • Date: 6 January 2020

Caribbean Sailing Grenada to St Lucia

  • Vessel: Rhea
  • Where: Grenada
  • Duration: 7 days
  • Date: 10 January 2020

Caribbean Sailing – Antigua to Guadeloupe

Live the Caribbean dream on board Eye of the Wind as she sails from Antigua to Guadeloupe, exploring the turquoise waters of the Caribbean Sea.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 10 January 2020

Caribbean Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 14 January 2020

Caribbean Sailing St Lucia to Grenada

  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 7 days
  • Date: 17 January 2020

Caribbean Sailing around Guadeloupe

Sail the turquoise Caribbean waters with Eye of the Wind as she makes her way around the island of Guadeloupe.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 17 January 2020

Caribbean Sailing Grenada to St Lucia

  • Vessel: Rhea
  • Where: Grenada
  • Duration: 7 days
  • Date: 24 January 2020

Caribbean Sailing – Guadeloupe, Dominica, Martinique

Sail southbound through the Caribbean Sea from Guadeloupe to Dominica before finishing on the beautiful island of Martinique.
  • Vessel: Eye of the Wind
  • Where: The Caribbean
  • Duration: 7 days
  • Date: 24 January 2020

Caribbean Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 28 January 2020

Caribbean Sailing St Lucia to Grenada

  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 7 days
  • Date: 31 January 2020

Caribbean Sailing Grenada to St Lucia

  • Vessel: Rhea
  • Where: Grenada
  • Duration: 7 days
  • Date: 7 February 2020

Caribbean Sailing – the Paradise of the BVI

Discover the beauty and paradise of the British Virgin Islands as you sail with Eye of the Wind from Saint Martin across the Caribbean Sea.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 7 February 2020

Caribbean Sailing, Tobago to Martinique

Sail and explore the culture of the colourful Caribbean islands on Twister as she sails from Tobago to Martinique.
  • Vessel: Twister
  • Where: Caribbean
  • Duration: 10 days
  • Date: 10 February 2020

Caribbean Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 11 February 2020

Caribbean Sailing St Lucia to Grenada

  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 7 days
  • Date: 14 February 2020

Caribbean Dreaming and Sailing around the BVI

Discover the paradise of the British Virgin Islands as you sail and explore these beautiful islands with Eye of the Wind.
  • Vessel: Eye of the Wind
  • Where: Caribbean
  • Duration: 7 days
  • Date: 14 February 2020

Caribbean Sailing, Martinique to Antigua

Sail and explore the culture of the colourful Caribbean islands on Twister as she sails from Martinique to Antigua.
  • Vessel: Twister
  • Where: Caribbean
  • Duration: 10 days
  • Date: 21 February 2020

Caribbean Sailing from Grenada

  • Vessel: Rhea
  • Where: Grenada
  • Duration: 7 days
  • Date: 21 February 2020

Caribbean Sailing around Grenada

Caribbean active sailing holiday onboard tall ship Blue Clipper exploring Grenada, St Vincent and the Grenadines.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 12 days
  • Date: 25 February 2020

Caribbean Sailing, Antigua to Tortola

Sail and explore the culture of the colourful Caribbean islands on Twister as she sails from Antigua to Tortola.
  • Vessel: Twister
  • Where: Caribbean
  • Duration: 10 days
  • Date: 4 March 2020

Caribbean Sailing from Grenada

  • Vessel: Rhea
  • Where: Grenada
  • Duration: 6 days
  • Date: 7 March 2020

Caribbean Sailing Grenada to St Martin

Caribbean active sailing holiday onboard tall ship Blue Clipper from Grenada to St Martin.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 15 days
  • Date: 10 March 2020

Caribbean Sailing from St Lucia to Antigua

  • Vessel: Rhea
  • Where: St Lucia
  • Duration: 5 days
  • Date: 27 March 2020

Caribbean Sailing St Martin to Antigua

Enjoy the azure ocean, palm beaches and the incomparable flair of the "Caribbean way of life" for spring sailing onboard luxury yacht Chronos.
  • Vessel: Chronos
  • Where: Caribbean
  • Duration: 11 days
  • Date: 28 March 2020

Ocean Sailing from Bermuda to the Azores

Cross the Atlantic ocean under sail on tall ship Blue Clipper as she sails from Bermuda to the Azores.
  • Vessel: Blue Clipper
  • Where: Caribbean
  • Duration: 25 days
  • Date: 11 April 2020
Scilly coastline in Summer

Destinations

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

View destinations
Tall Ships fleet

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