sailing holidays for all

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

Caribbean Christmas & New Year Sailing St Martin to Tortola BVI

22 December 2021, 14 days
Vessel: Chronos
Port: Caribbean

£4,700 Details

Summertime Sailing in Scandinavia

3 July 2021, 8 days
Vessel: Eye of the Wind
Port: Denmark/Sweden

£1,745 Details

Luxury Sailing from Corfu

24 July 2021, 8 days
Vessel: Chronos
Port: Greece

£2,820 Details

Sailing & Exploring the River Tamar

19 June 2021, 3 days
Vessel: Lynher
Port: Devon

£350 Details

Luxury Sailing from Corfu

31 July 2021, 8 days
Vessel: Chronos
Port: Greece

£2,820 Details

Devon Autumn Sailing Weekend

1 October 2021, 3 days
Vessel: Pilgrim of Brixham
Port: Devon

£275 Details

Island Hopping in The Hebrides

29 June 2021, 9 days
Vessel: Cherokee
Port: Scotland

£1,150 Details

Canary Island Exploring under Sail

13 December 2021, 7 days
Vessel: Twister
Port: The Canaries

£1,100 Details

Canary Island Exploring under Sail

6 December 2021, 7 days
Vessel: Twister
Port: The Canaries

£1,100 Details

Scandinavian Sailing from Sweden to Denmark

7 August 2021, 8 days
Vessel: Eye of the Wind
Port: Sweden/Denmark

£1,745 Details

Croatian Island Exploration

5 June 2021, 8 days
Vessel: Kairós
Port: Croatia

£2,220 Details

Sailing & Exploring the Hebrides

20 July 2021, 7 days
Vessel: Pellew
Port: Scotland

£1,020 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