Adventure Sailing Holidays
Climb aboard classic ships, luxury yachts or adventure vessels and explore a host of destinations as you’ve never seen them before. Let our fleet of boats give you an authentic taste of life under sail as you learn the ropes and experience a sailing holiday like no other. All our voyages are fully crewed so there’s no sailing experience needed to join a sailing holiday adventure!
Featured Sailing Holidays
Rare Species, Remarkable Coral & Remote Cultures of Indonesia
- 6 February 2023, 14 days
- Vessel: Ombak Putih
- Port: Indonesia
Sailing & Walking in the Hebrides
- 9 August 2023, 10 days
- Vessel: Steady
- Port: Oban, Scotland
Sailing the Firth of Clyde
- 25 May 2023, 6 days
- Vessel: Maybe
- Port: Firth of Clyde, Scotland
Isles of Scilly Sailing with Tall ship Irene
- 25 August 2023, 8 days
- Vessel: Irene
- Port: Newlyn, Cornwall
Luxury Island Hopping in Croatia
- 22 July 2023, 8 days
- Vessel: Kairós
- Port: Trogir, Croatia
Tall Ship Taster Sailing in Portugal
- 29 September 2023, 5 days
- Vessel: Maybe
- Port: Portugal
Whale Shark & Wildlife Watching in Indonesia
- 5 December 2023, 10 days
- Vessel: Ombak Putih
- Port: West Papau, Indonesia
Offshore Ocean Passage from Malaga to Tenerife
- 21 November 2023, 8 days
- Vessel: Rhea
- Port: Spain/Canaries
Tall Ship Sailing in the Caribbean
- 16 January 2024, 11 days
- Vessel: Blue Clipper
- Port: Grenada, Caribbean
Heritage Sailing on the South Devon Coast
- 28 April 2023, 4 days
- Vessel: Pilgrim of Brixham
- Port: Brixham, Devon
Sailing the Hebrides around Mull & Iona
- 29 April 2023, 7 days
- Vessel: Stravaigin
- Port: Oban, Scotland
Scandinavian Tall Ship Sailing from Copenhagen
- 21 August 2023, 6 days
- Vessel: Eye of the Wind
- Port: Denmark/Sweden
Destinations
Our range of vessels enables us to offer several destinations all over the globe. Which sailing holiday will you choose?
View Destinations
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“I’ve never sailed before, but if this is sailing, then I’m addicted. So, it seems, is everyone else: 85% of the Bessie Ellen’s guests return for further sailing adventures.”Hazel Southam, writing for The Guardian
“Having never set foot on a working tall ship, I had no idea what to expect aside from what I had seen in films. The reality is so much better. I would recommend anyone who loves the sea to try this.”Chris Baker, Muddy Stilettos Cornwall
“This was the Canaries of riding anchor in moonlit bays...., of swimming with turtles and and admiring pilot whales beneath our bows.”Andrew Eames, writing for The Times
“I thoroughly enjoyed reliving my youth onboard Bessie Ellen. We came from Cornwall to Oban on this beautiful ship with Skipper Nikki and her brilliant crew. Great hands on sailing, relaxed atmosphere and fabulous food. A true get away.”Kate Smith, Bessie Ellen Guest
Latest from our Adventure Journal
Be inspired to discover the world under sail! Read our latest journals below.
