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

Tall Ship Sailing around Skye from Ullapool to Mallaig

6 August 2022, 5 days
Vessel: Blue Clipper
Port: Ullapool, Scotland

£995.00 Details

Sailing Expedition from Iceland to the Faroe Islands & Hebrides

4 September 2022, 15 days
Vessel: Valiente
Port: Isafjordur, Iceland

£4,195.00 Details

Wildlife Cruising in Skye & the Small Isles

20 August 2022, 7 days
Vessel: Fleur de Lys
Port: Mallaig, Scotland

£1,550.00 Details

Bank Holiday Cruising in the Small Isles

26 August 2023, 4 days
Vessel: Fleur de Lys
Port: Mallaig, Scotland

£825.00 Details

Summer Sailing Holiday in Greece exploring the Saronic Islands

15 July 2023, 8 days
Vessel: Zorba
Port: Athens, Greece

£895.00 Details

Sailing the Hebrides, Orkneys & Shetland Islands

19 September 2022, 15 days
Vessel: Valiente
Port: Oban, Scotland

£4,195.00 Details

Cruise the Outer Hebrides; Barra & Uist

23 July 2022, 7 days
Vessel: Fleur de Lys
Port: Mallaig, Scotland

£1,550.00 Details

Bank Holiday Tall Ship Sailing in the Hebrides

27 August 2022, 5 days
Vessel: Blue Clipper
Port: Mallaig, Scotland

£995.00 Details

Sailing & Exploring Jura and Mull

22 July 2023, 7 days
Vessel: Steady
Port: Oban, Scotland

£1,130.00 Details

Cruising & Wildlife Watching in the Small Isles

27 May 2023, 6 days
Vessel: Fleur de Lys
Port: Mallaig, Scotland

£1,375.00 Details

Sailing Mull & the Small Isles

27 May 2023, 7 days
Vessel: Zuza
Port: Oban, Scotland

£1,195.00 Details

Sailing the Outer Hebrides, Shiants or Skye

19 May 2023, 7 days
Vessel: Zuza
Port: Oban, Scotland

£1,195.00 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