Offshore Sailing Adventures

Immerse yourself into life on the open water as you become part of the crew with an offshore sailing adventure. Learn the ropes under the guidance of professional crew as you get used to the rhythm of life at sea. Our offshore sailing adventures and mile building voyages are perfect for the adventure traveller and those seeking exhilarating holiday experiences.

We have found 39 voyages with berths available.

Offshore Sailing from Devon to Rotterdam

Sail with Cherokee from Devon, along the coast of the UK before crossing the English Channel to Rotterdam.
  • Date: 3 October 2023
  • Vessel: Cherokee
  • Duration: 9 days
  • Where: Devon/Netherlands

Sailing the Bay of the Biscay with Grayhound

Become part of the crew as you sail Cornish lugger Grayhound from Douarnenez to Bayona.
  • Date: 7 October 2023
  • Vessel: Grayhound
  • Duration: 10 days
  • Where: France/Spain

Adventure Sailing from Amsterdam to France

Immerse yourself into life at sea with an expedition sailing adventure on tall ship Eye of the Wind from Amsterdam to Brest.
  • Date: 13 October 2023
  • Vessel: Eye of the Wind
  • Duration: 11 days
  • Where: Netherlands/France

Luxury Sailing from Greece to Malta

Island hop and enjoy longer passages on the open water as luxury yacht Rhea sails from Greece to Malta.
  • Date: 21 October 2023
  • Vessel: Rhea
  • Duration: 8 days
  • Where: Greece/Malta

Offshore Sailing Passage from Spain to Cape Verde

Discover the world under sail with an offshore sailing adventure from Spain to Cape Verde with luxury yacht Chronos.
  • Date: 22 October 2023
  • Vessel: Chronos
  • Duration: 15 days
  • Where: Spain/Cape Verde

Offshore Passage Sailing the Bay of Biscay

Sail with Eye of the Wind as she makes her way from Brest, across the Bay of Biscay and down to the coast of Northern Spain. A great opportunity to build up sea miles!
  • Date: 23 October 2023
  • Vessel: Eye of the Wind
  • Duration: 8 days
  • Where: France/Spain

Atlantic Crossing From Spain & Christmas in the Caribbean

Immerse yourself into life at sea on traditional tall ship Florette as she sails from the Malaga in Spain over to the Canary Islands them on to the Caribbean island of Barbados. Spend Christmas in the tropical sunshine as you sail onward to the Grenadines and Martinique.
  • Date: 11 November 2023
  • Vessel: Florette
  • Duration: 54 days
  • Where: Malaga Spain /Caribbean

Atlantic Crossing from Spain to Barbados

Immerse yourself into life at sea on traditional tall ship Florette as she sails from Spain to the Caribbean island of Barbados.
  • Date: 11 November 2023
  • Vessel: Florette
  • Duration: 38 days
  • Where: Spain/Caribbean

Offshore Ocean Passage from Malta to Malaga

Sail with luxury yacht Rhea from the island of Malta to the Spanish coastal town of Malaga.
  • Date: 12 November 2023
  • Vessel: Rhea
  • Duration: 8 days
  • Where: Malta/Spain

Offshore Ocean Passage from Malta to Greece

Sail with luxury yacht Kairos from the island of Malta to the Greek island of Aegina.
  • Date: 18 November 2023
  • Vessel: Kairós
  • Duration: 8 days
  • Where: Malta/Greece

Offshore Ocean Passage from Malaga to Tenerife

Enjoy offshore adventure sailing from Malaga to Tenerife with luxury yacht Rhea.
  • Date: 21 November 2023
  • Vessel: Rhea
  • Duration: 8 days
  • Where: Spain/Canaries

Offshore Ocean Passage from Tenerife to the Caribbean

Sail with luxury yacht Rhea from Tenerife, across the Atlantic Ocean to the Caribbean island of St Martin.
  • Date: 28 November 2023
  • Vessel: Rhea
  • Duration: 23 days
  • Where: Canaries/Caribbean

Offshore Atlantic Sailing with Grayhound

Set sail with Grayhound on the first Leg of her Atlantic crossing from Portugal to the Canary Islands via Madeira.
  • Date: 12 December 2023
  • Vessel: Grayhound
  • Duration: 12 days
  • Where: Portugal/Canaries

Luxury Sailing from BVI to the Dominican Republic

Sail with classic yacht Rhea from Tortola to the Dominican Republic for a hands-on sailing adventure.
  • Date: 24 January 2024
  • Vessel: Rhea
  • Duration: 8 days
  • Where: BVI, Caribbean

Caribbean Sailing from Tobago with Grayhound

Explore the Caribbean islands from Tobago to St Lucia with traditional wooden lugger Grayhound.
  • Date: 13 February 2024
  • Vessel: Grayhound
  • Duration: 6 days
  • Where: Tobago, Caribbean

Caribbean Sailing from St Lucia with Grayhound

Explore the Caribbean islands from St Lucia with traditional wooden lugger Grayhound.
  • Date: 21 February 2024
  • Vessel: Grayhound
  • Duration: 6 days
  • Where: St Lucia, Caribbean

Caribbean Sailing from St Lucia with Grayhound

Explore the Caribbean islands from St Lucia with traditional wooden lugger Grayhound.
  • Date: 28 February 2024
  • Vessel: Grayhound
  • Duration: 6 days
  • Where: St Lucia, Caribbean

Offshore Sailing from Samana to St Martin

Sail with classic yacht Rhea from the Dominican Republic to the Caribbean island of St Martin for a hands-on sailing adventure.
  • Date: 3 March 2024
  • Vessel: Rhea
  • Duration: 7 days
  • Where: Caribbean

Caribbean Sailing from St Lucia with Grayhound

Explore the Caribbean islands from St Lucia to Guadeloupe with traditional wooden lugger Grayhound.
  • Date: 6 March 2024
  • Vessel: Grayhound
  • Duration: 7 days
  • Where: St Lucia, Caribbean

Offshore Atlantic Crossing with Grayhound

Experience an Atlantic crossing sailing adventure from the Caribbean to the Azores on lugger Grayhound!
  • Date: 19 March 2024
  • Vessel: Grayhound
  • Duration: 32 days
  • Where: Atlantic Crossing

Offshore Sailing from Amsterdam to Inverness

Sail with the Flying Dutchman from Amsterdam to the Scottish coast as you visit Holy island along the way.
  • Date: 20 March 2024
  • Vessel: Flying Dutchman
  • Duration: 9 days
  • Where: Amsterdam/Scotland

Offshore Sailing from the Netherlands to Dover

Join adventure yacht Steady as she sails from her homeport in Holland, crossing the North Sea to finish in the English port of Dover.
  • Date: 6 April 2024
  • Vessel: Steady
  • Duration: 7 days
  • Where: Netherlands/UK

Offshore Sailing Passage 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: 23 April 2024
  • Vessel: Chronos
  • Duration: 22 days
  • Where: Antigua/Gibraltar

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 2024
  • Vessel: Rhea
  • Duration: 17 days
  • Where: Antigua/Azores

Expedition Sailing from Tromsø to Svalbard

Sail from Tromsø to Svalbard via Bear island with expedition yacht Valiente.
  • Date: 25 April 2024
  • Vessel: Valiente
  • Duration: 8 days
  • Where: Norway/Svalbard

Offshore Sailing from Cornwall to Ireland

Sail with adventure yacht Steady as she swaps one Celtic coast for another with an offshore sailing experience from Cornwall to Ireland.
  • Date: 27 April 2024
  • Vessel: Steady
  • Duration: 10 days
  • Where: UK/Ireland

Atlantic Crossing with Tall Ship Florette

Immerse yourself into life at sea on traditional tall ship Florette as she sails from Martinique to the Azores.
  • Date: 4 May 2024
  • Vessel: Florette
  • Duration: 28 days
  • Where: Caribbean/Azores

Atlantic Crossing with Tall Ship Florette

Set sail on an Atlantic adventure with tall ship Florette as she journeys from Martinique to Cornwall via the Azores.
  • Date: 4 May 2024
  • Vessel: Florette
  • Duration: 50 days
  • Where: Caribbean/Azores/Cornwall

Offshore Ocean Passage from the Azores to Gibraltar

Sail from the Atlantic archipelago of the Azores to the port city of Gibraltar with luxury yacht Rhea.
  • Date: 10 May 2024
  • Vessel: Rhea
  • Duration: 8 days
  • Where: Azores/Gibraltar

Offshore Sailing from the Azores to Cornwall

Immerse yourself into life at sea on traditional tall ship Florette as she sails from the Azores to Falmouth, Cornwall.
  • Date: 8 June 2024
  • Vessel: Florette
  • Duration: 15 days
  • Where: Azores/Cornwall

Mile Builder Sailing from Devon to Cornwall

Join Pilgrim of Brixham for a mile building sailing experience as she sails from Brixham, Devon to Falmouth, Cornwall.
  • Date: 8 June 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Devon/Cornwall

Mile Building Taster from Cornwall to Devon

Join Pilgrim of Brixham for a mile building sailing experience as she sails from Falmouth, Cornwall to Brixham, Devon.
  • Date: 24 July 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Cornwall/Devon

Offshore Sailing from Cornwall to Spain

Enjoy an offshore sailing adventure from Cornwall to Spain with pilot cutter Pellew as she crosses the Bay of Biscay.
  • Date: 25 July 2024
  • Vessel: Pellew
  • Duration: 8 days
  • Where: Cornwall/Spain

Offshore Sailing Adventure from Cornwall to Spain

Sail with tall ship Blue Clipper for an ocean crossing experience from Falmouth, Cornwall to La Coruna, Spain.
  • Date: 24 August 2024
  • Vessel: Blue Clipper
  • Duration: 10 days
  • Where: Cornwall, Spain

Offshore Sailing from Spain to Cornwall

Enjoy an offshore sailing adventure from Spain to Cornwall with pilot cutter Pellew as she crosses the Bay of Biscay.
  • Date: 3 September 2024
  • Vessel: Pellew
  • Duration: 9 days
  • Where: Spain/Cornwall

Offshore Sailing from Inverness to Amsterdam

Sail with the Flying Dutchman from Inverness to Amsterdam as you visit Holy island along the way.
  • Date: 26 October 2024
  • Vessel: Flying Dutchman
  • Duration: 9 days
  • Where: Scotland/Amsterdam

Offshore Sailing Passage from Athens to Gibraltar

Enjoy offshore sailing across the Mediterranean Sea with luxury yacht Rhea from Athens, Greece to Gibraltar.
  • Date: 7 November 2024
  • Vessel: Rhea
  • Duration: 14 days
  • Where: Greece/Gibraltar

Offshore Sailing Passage from Gibraltar to Tenerife

Sail from the port city of Gibraltar to the Canary Island of Tenerife with luxury yacht Rhea.
  • Date: 21 November 2024
  • Vessel: Rhea
  • Duration: 7 days
  • Where: Gibraltar/Canary Islands

Offshore Sailing Passage from Tenerife to Martinique

Sail with the crew of Rhea as they set sail from Tenerife to the island of Martinique in the Caribbean.
  • Date: 28 November 2024
  • Vessel: Rhea
  • Duration: 23 days
  • Where: Tenerife/Caribbean
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