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

Luxury Sailing in Malta

21 May 2022, 4 days
Vessel: Chronos
Port: Malta

£1,070 Details

Bank Holiday Sailing in the Hebrides

29 April 2022, 4 days
Vessel: Stravaigin
Port: Scotland

£620 Details

Weekend Sailing in Venice

25 March 2022, 5 days
Vessel: Kairós
Port: Italy

£1,190 Details

All Inclusive Canary Islands Sailing Holiday

5 February 2022, 7 days
Vessel: Twister
Port: Tenerife, Canary Islands

£1,100 Details

Caribbean Tall Ship Sailing

28 January 2022, 8 days
Vessel: Eye of the Wind
Port: Caribbean

£1,690 Details

Spring Bank Holiday Sailing Weekend

29 April 2022, 4 days
Vessel: Pettifox
Port: Cornwall

£2,080 Details

Taster sailing in the Hebrides; Exploring Mull

18 July 2022, 4 days
Vessel: Skyelark
Port: Scotland

£855 Details

Sailing & Exploring Svalbard

4 July 2023, 16 days
Vessel: Noorderlicht
Port: Svalbard,Norway

£5,085 Details

Adventure Sailing in Svalbard

19 August 2023, 8 days
Vessel: Noorderlicht
Port: Svalbard,Norway

£2,400 Details

Luxury Caribbean Sailing from Barbados

8 January 2022, 8 days
Vessel: Chronos
Port: Caribbean

£2,460 Details

Caribbean Christmas Sailing Grenada to St Lucia

22 December 2021, 8 days
Vessel: Chronos
Port: Grenada

£2,260 Details

Cruising & Wildlife watching in Skye

30 July 2022, 6 days
Vessel: Fleur de Lys
Port: Mallaig, Scotland

£1,500 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