Expedition Sailing Holidays

Our expedition sailing holidays are designed to take you on a thrilling journey to discover some of the world’s most stunning and remote locations. From exploring the Arctic wilderness, navigating through the most remote islands of Scotland, or building your sea miles on an ocean crossing, join our expedition sailing holidays for the adventure of a lifetime.

We have found 61 voyages with berths available.

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Ski & Sail Expedition in Norway

Join tall ship Noorderlicht in the Arctic circle for a Ski & Sail adventure from Alta to Tromsø.
  • Date: 23 March 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Northern Norway
  • Board type: Full Board

Tall Ship Sailing in the Orkney Islands

Explore the Outer Hebrides, Orkney Islands and Skye with tall ship the Flying Dutchman.
  • Date: 5 April 2024
  • Vessel: Flying Dutchman
  • Duration: 10 days
  • Where: Scotland
  • Board type: Half Board

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
  • Board type: Full Board

Expedition Sailing from Tromsø to Svalbard

Set sail for an Arctic expedition on tall ship Noorderlicht as she sails from Tromsø to the remote archipelago of Svalbard.
  • Date: 8 April 2024
  • Vessel: Noorderlicht
  • Duration: 10 days
  • Where: Northern Norway
  • Board type: Full Board

Offshore Ocean Sailing from Cape Town to the Azores

Set sail from Cape Town for an offshore sailing adventure to the Azores with expedition boat Tecla.
  • Date: 12 April 2024
  • Vessel: Tecla
  • Duration: 47 days
  • Where: Cape Town/Azores
  • Board type: Full Board

Mile Builder Sailing from Portugal to Monaco

Sail with tall ship Blue Clipper for a Mediterranean mile builder from Portugal to Monaco.
  • Date: 14 April 2024
  • Vessel: Blue Clipper
  • Duration: 10 days
  • Where: Portugal/Monaco
  • Board type: Full Board

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
  • Board type: Full Board

Mile Builder Sailing from Monaco to Portugal

Sail with tall ship Blue Clipper for a Mediterranean mile builder from Monaco to Portugal.
  • Date: 27 April 2024
  • Vessel: Blue Clipper
  • Duration: 8 days
  • Where: Monaco/Portugal
  • Board type: Full Board

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
  • Board type: Full Board

Offshore Sailing from Portugal to Cornwall

Sail with tall ship Blue Clipper for an Ocean mile builder from the South coast of Portugal to Cornwall.
  • Date: 5 May 2024
  • Vessel: Blue Clipper
  • Duration: 11 days
  • Where: Portugal/Cornwall
  • Board type: Full Board

Adventure Sailing from Ireland to Scotland

Sail from Belfast to Scotland with adventure yacht Steady as she island hops through the inner Hebrides.
  • Date: 8 May 2024
  • Vessel: Steady
  • Duration: 8 days
  • Where: Ireland/Scotland
  • Board type: Full Board

Sailing the Outer Hebrides; Isles of Lewis & Harris

Journey to the myth shrouded Outer Hebrides of Scotland with expedition yacht Zuza. Explore the remote Shiants and the Isles of Lewis, Harris & Skye.
  • Date: 24 May 2024
  • Vessel: Zuza
  • Duration: 7 days
  • Where: Oban, Scotland
  • Board type: Full Board

Sailing in Svalbard; Arctic Spring

Discover the beauty of the Arctic wilderness from Svalbard on tall ship Noorderlicht.
  • Date: 26 May 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Offshore Adventure Sailing from the Azores to Scotland

Set sail with expedition boat Tecla as she sails from the Azores to Ullapool on the West coast of Scotland.
  • Date: 30 May 2024
  • Vessel: Tecla
  • Duration: 19 days
  • Where: Azores/Scotland
  • Board type: Full Board

Sailing in Svalbard; Arctic Spring

Discover the beauty of the Arctic wilderness from Svalbard on tall ship Noorderlicht.
  • Date: 2 June 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Ski & Sail Expedition in Svalbard

Explore the Arctic archipelago of Svalbard with a ski and sail adventure on expedition yacht Valiente.
  • Date: 3 June 2024
  • Vessel: Valiente
  • Duration: 9 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing Adventure to St Kilda

Sail with expedition yacht Zuza to the UNESCO world heritage island of St Kilda off the West coast of Scotland.
  • Date: 6 June 2024
  • Vessel: Zuza
  • Duration: 10 days
  • Where: Oban, Scotland
  • Board type: Full Board

Sailing in Svalbard; Arctic Spring

Discover the beauty of the Arctic wilderness from Svalbard on tall ship Noorderlicht.
  • Date: 9 June 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing & Wildlife watching in the Outer Hebrides

Journey to the myth shrouded Outer Hebrides of Scotland with expedition yacht Zuza. Explore the remote Shiants and the Isles of Lewis, Harris & Skye.
  • Date: 17 June 2024
  • Vessel: Zuza
  • Duration: 7 days
  • Where: Oban, Scotland
  • Board type: Full Board

Sustainable Sailing in Svalbard, Norway

Spend 11 days sailing and exploring the Arctic archipelago of Svalbard with sustainable tall ship Noorderlicht.
  • Date: 18 June 2024
  • Vessel: Noorderlicht
  • Duration: 11 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Adventure Sailing from Scotland to Iceland

Set sail from Scotland as you explore the Orkney's, Shetlands and Faroe Islands before an open water crossing the Iceland.
  • Date: 19 June 2024
  • Vessel: Tecla
  • Duration: 22 days
  • Where: Scotland/Iceland
  • Board type: Full Board

Sailing in the Outer Hebrides & St Kilda

Journey with Scottish yacht Stravaigin as she explores the magic of the Outer Hebrides & St Kilda under sail.
  • Date: 21 June 2024
  • Vessel: Stravaigin
  • Duration: 10 days
  • Where: Outer Hebrides, Scotland
  • Board type: Full Board

Arctic Circle sailing; Svalbard Expedition

Explore the fascinating fjords and glaciers of the fragile Arctic archipelago of Svalbard with expedition yacht Valiente.
  • Date: 22 June 2024
  • Vessel: Valiente
  • Duration: 10 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing Expedition in Svalbard; 16 day circumnavigation

Spend 16 days circumnavigating the Arctic wonders of Svalbard with tall ship Noorderlicht.
  • Date: 30 June 2024
  • Vessel: Noorderlicht
  • Duration: 16 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Arctic Circle sailing; Svalbard Expedition

Explore the fascinating fjords and glaciers of the fragile Arctic archipelago of Svalbard with expedition yacht Valiente.
  • Date: 2 July 2024
  • Vessel: Valiente
  • Duration: 10 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing Skye, The Small Isles & the Outer Hebrides

Sail from Mallaig on the west coast of Scotland as you explore the Outer Hebridean islands of Lewis and Harris with yacht Zuza.
  • Date: 2 July 2024
  • Vessel: Zuza
  • Duration: 7 days
  • Where: Mallaig, Scotland
  • Board type: Full Board

Discover the Outer Hebrides, Skye & the Small Isles

Sail from Mallaig on the west coast of Scotland as you explore the Outer Hebridean islands of Lewis and Harris with yacht Zuza.
  • Date: 9 July 2024
  • Vessel: Zuza
  • Duration: 7 days
  • Where: Mallaig, Scotland
  • Board type: Full Board

Sailing Skye, The Small Isles & the Outer Hebrides

Sail from Mallaig on the west coast of Scotland as you explore the Outer Hebridean islands of Lewis and Harris with yacht Zuza.
  • Date: 17 July 2024
  • Vessel: Zuza
  • Duration: 7 days
  • Where: Mallaig, Scotland
  • Board type: Full Board

Sailing the Isles Lewis & Harris in the Outer Hebrides

Sail from Mallaig on the west coast of Scotland as you explore the Outer Hebridean islands of Lewis and Harris with yacht Zuza.
  • Date: 24 July 2024
  • Vessel: Zuza
  • Duration: 7 days
  • Where: Mallaig, Scotland
  • Board type: Full Board

Tall ship Sailing Outer Hebrides and St Kilda

Sail to the Outer Hebrides, Shiant Islands and remote UNESCO world heritage site of St Kilda on the West coast of Scotland with tall ship Blue Clipper.
  • Date: 27 July 2024
  • Vessel: Blue Clipper
  • Duration: 8 days
  • Where: Mallaig, Scotland
  • Board type: Full Board

Sailing Svalbard Expedition; around Spitsbergen

Discover the land of the midnight sun with an expedition sailing holiday in the Arctic Circle around the archipelago of Svalbard.
  • Date: 28 July 2024
  • Vessel: Valiente
  • Duration: 12 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing Expedition in Svalbard; 16 day circumnavigation

Spend 16 days circumnavigating the Arctic wonders of Svalbard with tall ship Noorderlicht.
  • Date: 31 July 2024
  • Vessel: Noorderlicht
  • Duration: 16 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing Adventure to St Kilda, Scotland

Sail with expedition yacht Zuza to the UNESCO world heritage island of St Kilda off the West coast of Scotland from Mallaig to Oban.
  • Date: 1 August 2024
  • Vessel: Zuza
  • Duration: 10 days
  • Where: Mallaig, Scotland
  • Board type: Full Board

Explore the Outer Hebrides & St Kilda

Explore the Outer Hebrides and UNESCO archipelago of St Kilda with traditional tall ship the Flying Dutchman.
  • Date: 3 August 2024
  • Vessel: Flying Dutchman
  • Duration: 9 days
  • Where: Ullapool, Scotland
  • Board type: Half Board

Sailing Svalbard Expedition around Spitsbergen

Discover the land of the midnight sun with an expedition sailing holiday in the Arctic Circle around the archipelago of Svalbard.
  • Date: 9 August 2024
  • Vessel: Valiente
  • Duration: 12 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing Expedition in Svalbard; 16 day circumnavigation

Spend 16 days circumnavigating the Arctic wonders of Svalbard with tall ship Noorderlicht.
  • Date: 15 August 2024
  • Vessel: Noorderlicht
  • Duration: 16 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Expedition Sailing; Svalbard, Greenland & Iceland

Discover Arctic waters as you sail with expedition boat Valiente from Svalbard, to Greenland and on to the shores of Iceland.
  • Date: 21 August 2024
  • Vessel: Valiente
  • Duration: 14 days
  • Where: Svalbard/Iceland
  • Board type: Full Board

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
  • Board type: Full Board

Adventure Sailing in Svalbard, Norway

Explore the fragile archipelago of Svalbard with a sustainable sailing holiday on tall ship Noorderlicht.
  • Date: 1 September 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Adventure Sailing in Greenland & Iceland

Set sail for the South of Greenland before an open water crossing to discover the black sandy shores of Iceland.
  • Date: 2 September 2024
  • Vessel: Tecla
  • Duration: 20 days
  • Where: Greenland/Iceland
  • Board type: Full Board

Expedition Sailing from Iceland to Faroe and Scotland

Sail from the Arctic shores of Iceland to the Faroe Islands before finishing on West coast of Scotland with expedition vessel Valiente.
  • Date: 4 September 2024
  • Vessel: Valiente
  • Duration: 15 days
  • Where: Iceland/Scotland
  • Board type: Full Board

Adventure Sailing in Svalbard, Norway

Explore the fragile archipelago of Svalbard with a sustainable sailing holiday on tall ship Noorderlicht.
  • Date: 8 September 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sail Adventure from Ireland to France

Sail Cornish lugger Grayhound on a hands-on sailing adventure from Belfast, Ireland to the coast of France!
  • Date: 11 September 2024
  • Vessel: Grayhound
  • Duration: 8 days
  • Where: Ireland/France
  • Board type: Full Board

Adventure Sailing in Svalbard, Norway

Explore the fragile archipelago of Svalbard with a sustainable sailing holiday on tall ship Noorderlicht.
  • Date: 15 September 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Adventure Sailing in Svalbard, Norway

Explore the fragile archipelago of Svalbard with a sustainable sailing holiday on tall ship Noorderlicht.
  • Date: 22 September 2024
  • Vessel: Noorderlicht
  • Duration: 8 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Adventure Sailing from Iceland to Scotland

Set sail from Iceland as you explore the Faroe's, Orkney's and Shetland Islands before finishing in Scotland.
  • Date: 22 September 2024
  • Vessel: Tecla
  • Duration: 23 days
  • Where: Scotland/Iceland
  • Board type: Full Board

Scotland to Norway Adventure via Orkney and Shetland islands

Follow in the footsteps of the vikings as Valiente sails from the West coast of Scotland, to the Orkney and Shetland islands before finishing in Bergen, Norway.
  • Date: 24 September 2024
  • Vessel: Valiente
  • Duration: 15 days
  • Where: Scotland/Norway
  • Board type: Full Board

Offshore Sailing from Scotland to Tenerife

Sail from Scotland to Tenerife with expedition boat Tecla for an Ocean adventure to remember!
  • Date: 17 October 2024
  • Vessel: Tecla
  • Duration: 26 days
  • Where: Scotland/Tenerife
  • Board type: Full Board

Atlantic Sailing from Tenerife to the Falkland Islands

Join expedition boat Tecla for an Atlantic crossing adventure from Tenerife to the Falkland Islands.
  • Date: 11 November 2024
  • Vessel: Tecla
  • Duration: 18 days
  • Where: Tenerife/Falkland Islands
  • Board type: Full Board

Whale watching & Northern Light Sailing in Norway

Enjoy whale watching and northern lights in Northern Norway with expedition yacht Valiente.
  • Date: 13 November 2024
  • Vessel: Valiente
  • Duration: 5 days
  • Where: Tromsø, Norway
  • Board type: Full Board

Whale watching & Northern Light Sailing in Norway

Enjoy whale watching and northern lights in Northern Norway with expedition yacht Valiente.
  • Date: 20 November 2024
  • Vessel: Valiente
  • Duration: 5 days
  • Where: Tromsø, Norway
  • Board type: Full Board

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
  • Board type: Full Board

Whale watching & Northern Light Sailing in Norway

Enjoy whale watching and northern lights in Northern Norway with expedition yacht Valiente.
  • Date: 4 December 2024
  • Vessel: Valiente
  • Duration: 5 days
  • Where: Tromsø, Norway
  • Board type: Full Board

Offshore Sailing from the Netherlands to Inverness

Join adventure yacht Steady as she sails from her homeport in Holland, crossing the North Sea to finish in the Scottish port of Inverness.
  • Date: 11 April 2025
  • Vessel: Steady
  • Duration: 11 days
  • Where: Netherlands/Scotland
  • Board type: Full Board

Expedition Sailing from Tromsø to Svalbard

Sail from Tromsø to Svalbard via Bear island with expedition yacht Valiente.
  • Date: 25 April 2025
  • Vessel: Valiente
  • Duration: 8 days
  • Where: Norway/Svalbard
  • Board type: Full Board

Ski & Sail Expedition in Svalbard

Explore the Arctic archipelago of Svalbard with a ski and sail adventure on expedition yacht Valiente.
  • Date: 9 May 2025
  • Vessel: Valiente
  • Duration: 7 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Ski & Sail Expedition in Svalbard

Explore the Arctic archipelago of Svalbard with a ski and sail adventure on expedition yacht Valiente.
  • Date: 16 May 2025
  • Vessel: Valiente
  • Duration: 7 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Ski & Sail Expedition in Svalbard

Explore the Arctic archipelago of Svalbard with a ski and sail adventure on expedition yacht Valiente.
  • Date: 23 May 2025
  • Vessel: Valiente
  • Duration: 9 days
  • Where: Svalbard, Norway
  • Board type: Full Board

Sailing in the Outer Hebrides

Explore the Outer Hebrides and the remote Shiant islands on the West Coast of Scotland with expedition yacht Steady.
  • Date: 29 June 2025
  • Vessel: Steady
  • Duration: 8 days
  • Where: Ullapool, Scotland
  • Board type: Full Board

Sailing in the Outer Hebrides

Explore the Outer Hebrides and the remote Shiant islands on the West Coast of Scotland with expedition yacht Steady.
  • Date: 10 July 2025
  • Vessel: Steady
  • Duration: 8 days
  • Where: Ullapool, Scotland
  • Board type: Full Board

Luxury Sailing in Cape Verde

Explore the tropical archipelago of Cape Verde with a luxury sailing holiday on classic yacht Chronos.
  • Date: 21 November 2025
  • Vessel: Chronos
  • Duration: 13 days
  • Where: Cape Verde
  • Board type: Full Board
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