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

Bank Holiday Tall Ship Sailing in the Hebrides

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

£995.00 Details

CRUISING & WILDLIFE WATCHING IN THE SMALL ISLES

9 September 2023, 7 days
Vessel: Fleur de Lys
Port: Mallaig, Scotland

£1,650.00 Details

Taster Sailing the Firth of Clyde

17 July 2023, 4 days
Vessel: Maybe
Port: Firth of Clyde, Scotland

£695.00 Details

Sailing in Greece; Naxos to Athens

3 September 2022, 8 days
Vessel: Zorba
Port: Naxos, Greece

£1,150.00 Details

Sunshine Sailing in the Saronic Islands, Greece

21 October 2023, 8 days
Vessel: Zorba
Port: Athens, Greece

£895.00 Details

Island Hopping & Sailing around the Saronic Islands

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

£895.00 Details

Isles of Scilly Sailing with Tall ship Irene

4 September 2022, 7 days
Vessel: Irene
Port: Newlyn, Cornwall

£1,350.00 Details

Luxury New Year Sailing in the Caribbean

28 December 2022, 8 days
Vessel: Chronos
Port: St Lucia, Caribbean

£2,670.00 Details

A Sailors’ Voyage to Scotland

29 April 2023, 10 days
Vessel: Bessie Ellen
Port: Fowey, Cornwall

£1,550.00 Details

Sailing the coast of Croatia

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

£2,400.00 Details

Hebridean Exploring around Mull & the Isles

24 June 2023, 7 days
Vessel: Bessie Ellen
Port: Oban, Scotland

£1,250.00 Details

Wildlife Weekend Cruise Around the Small Isles

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

£1,550.00 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