Offshore sailing expedition vacations
An offshore sailing vacation is like an escape into the unknown where you’ll lose sight of land and learn what it takes to become a master sailor in the company of proven professionals. From RYA qualifications and extending skippering skills to beginners being able to join a crew in the Atlantic, Caribbean or the English Channel, this is where all of your offshore sailing wishes come to fruition.
21 Offshore sailing expedition vacations found
Arctic Circle sailing expedition, Spitsbergen
Unique opportunity to experience Arctic wildlife & scenery
From NKr72,300 12 days ex flights
Small group travel:
2027: 19 Jul, 31 Jul
Late availability on August 2026 departures - enquire now!
Sail the North Coast 500, Scotland
Adventure sailing around the north coast of Scotland
From £2,495 27 days ex flights
Small group travel:
2027: 19 Jun
Baltic Sea sailing expedition
Kiel, Copenhagen, Gdansk: three legs, one Baltic adventure
From £3,495 10 days ex flights
Small group travel:
2027: 29 May, 10 Jun, 23 Jun
Faroe Islands sailing vacation
Island hopping through Europe's wild Faroe Islands
From €2,099 9 days ex flights
Small group travel:
2027: 10 Jul
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Orkney, Fair Isle & Shetland sailing vacation
Hands on sailing to Scotland’s most remote islands
From €2,339 11 days ex flights
Small group travel:
2027: 8 Jun
Svalbard to Iceland Arctic sailing expedition
Arctic sailing adventure to Jan Mayen, Greenland & Iceland
From €3,615 14 days per accommodation
Small group travel
Tanzania sailing expedition
Explore Pemba, Mafia and Zanzibar under sail
From £3,495 10 days ex flights
Small group travel:
2027: 3 Apr, 21 May
Central Azores sailing vacation, island hopping
Island-hopping adventure: sail & explore the Azores
From €2,149 10 days ex flights
Small group travel:
2026: 13 Aug
Azores sailing vacation, Central & Southern islands
Sail the Central & Southern Azores islands
From €2,395 10 days ex flights
Small group travel
Arctic sailing safari
Navigate icy waters to spot polar bears and whales
From €2,415 7 days ex flights
Small group travel:
2026: 30 Aug
Remote Svalbard sailing expedition
Sail beyond civilization into Svalbard’s wild icy frontier
From €5,380 21 days ex flights
Small group travel:
2026: 23 Aug
Greenland sailing expedition, Scoresby Sund
Sail the world’s largest fjord system + solar eclipse 2026
From €5,500 14 days ex flights
Small group travel
Sailing in the Azores, Central & Northern Islands
Sail & explore the Central and North-western Islands
From €2,849 12 days ex flights
Small group travel
Azores sailing vacation, Central Islands
Explore the Azores far away from mass tourism
From €2,399 12 days ex flights
Small group travel
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Zanzibar to the Seychelles sailing expedition
Ideal for adventurous spirits to experience bluewater sailing
From £3,995 16 days ex flights
Small group travel:
2027: 15 Apr
Cape Town to St Helena sailing expedition
Cross the South Atlantic ocean with a world class skipper
From £5,995 21 days ex flights
Small group travel:
2026: 12 Oct
2027: 1 Mar, 10 May, 26 Jul, 25 Oct
2027: 1 Mar, 10 May, 26 Jul, 25 Oct
St Helena to Cape Town sailing expedition
Sail one of the most remote stretches of ocean on Earth
From £5,995 21 days ex flights
Small group travel:
2026: 12 Oct
2027: 25 Mar, 3 Jun, 19 Aug, 18 Nov
2027: 25 Mar, 3 Jun, 19 Aug, 18 Nov
Madagascar to Zanzibar sailing expedition
An 850+ nautical miles ocean crossing adventure!
From £3,995 16 days ex flights
Small group travel:
2027: 3 May
Sail across the South Atlantic Ocean
Epic Adventure Sailing! Cape Town to St Helena roundtrip
From £7,495 40 days ex flights
Small group travel:
2026: 12 Oct
Hjorundfjord sailing holiday in Norway
Sailing voyage Norway – Islandhopping & Hjørundfjord & Runde
From €2,049 9 days ex flights
Small group travel:
2027: 2 Sep
Lofoten islands sailing vacation, Norway
Lofoten’s mountains & Fjords are best explored by sailboat
From NKr27,500 to NKr31,500 8 days ex flights
Small group travel:
2026: 7 Sep
2027: 7 Jun, 15 Jun, 26 Jul, 7 Aug, 20 Aug
2027: 7 Jun, 15 Jun, 26 Jul, 7 Aug, 20 Aug
Late availability on August 2026 departures - enquire now!
