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!

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Featured Sailing Holidays

Cruising & Wildlife watching in the Outer Hebrides

25 June 2022, 6 days
Vessel: Fleur de Lys
Port: Scotland

£1,500 Details

Cornwall & Scilly Sailing Jubilee Adventure

29 May 2022, 8 days
Vessel: Maybe
Port: Cornwall

£1,490 Details

Sailing & Exploring Mull

4 June 2022, 7 days
Vessel: Pellew
Port: Scotland

£1,100 Details

Sailing to the Channel Islands

8 September 2022, 8 days
Vessel: Pilgrim of Brixham
Port: The Channel Islands

£975 Details

Tall Ship Sailing & Exploring the Aeolian Islands

16 July 2022, 8 days
Vessel: Florette
Port: Italy

£1,350 Details

Isles of Scilly Sailing with Cornish Lugger Grayhound

10 May 2022, 7 days
Vessel: Grayhound
Port: Cornwall

£1,250 Details

Sailing the coast of Croatia

6 August 2022, 8 days
Vessel: Kairós
Port: Croatia

£2,400 Details

Falmouth Classics & Sea Shanty Festival

16 June 2022, 5 days
Vessel: Agnes
Port: Cornwall

£680 Details

Sailing the Caledonian Canal and Great Glen Way

4 May 2022, 7 days
Vessel: Steady
Port: Scotland

£1,030 Details

Sailing & Whale Watching in the Hebrides

13 August 2022, 7 days
Vessel: Bessie Ellen
Port: Scotland

£1,105 Details

Sailing the Outer Hebrides

20 August 2022, 7 days
Vessel: Bessie Ellen
Port: Scotland

£1,105 Details

Sailing & Walking in the Hebrides

21 May 2022, 10 days
Vessel: Steady
Port: Scotland

£1,415 Details

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Destinations

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

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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.

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“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