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!

View all voyages

Featured Sailing Holidays

Sailing & Exploring Isfjorden, Svalbard

3 September 2022, 7 days
Vessel: Noorderlicht // Reade Swan
Port: Svalbard, Norway

£1,820.00 Details

Sailing & Exploring Jura and Mull

30 July 2022, 7 days
Vessel: Steady
Port: Oban, Scotland

£1,030.00 Details

Sailing Weekend in Cornwall

27 May 2022, 3 days
Vessel: Pettifox
Port: Fowey, Cornwall

£200.00 Details

Falmouth Classics & Sea Shanty Festival

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

£680.00 Details

Tall Ship Sailing in the Isles of Scilly

1 September 2022, 8 days
Vessel: Maybe
Port: Cornwall

£1,490.00 Details

Sailing & Walking in the Hebrides

9 August 2023, 10 days
Vessel: Steady
Port: Oban, Scotland

£1,550.00 Details

Sailing & Exploring Mull

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

£1,100.00 Details

Coronation Jubilee Sailing in Devon

1 June 2022, 5 days
Vessel: Pilgrim of Brixham
Port: Brixham, Devon

£575.00 Details

Sailing Svalbard Expedition to Sjuøyane

9 July 2022, 10 days
Vessel: Valiente
Port: Svalbard, Norway

£4,175.00 Details

Sailing in Greece; Exploring the Cyclades

13 August 2022, 8 days
Vessel: Zorba
Port: Naxos, Greece

£1,150.00 Details

Sailing Mull & the Small Isles

1 September 2023, 7 days
Vessel: Zuza
Port: Oban, Scotland

£1,195.00 Details

Sailing in Greece; Exploring the Cyclades

20 August 2022, 8 days
Vessel: Zorba
Port: Naxos, Greece

£1,150.00 Details

Search for more in our Voyage Finder

Destinations

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

View Destinations

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.

View Fleet

“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