classic holidays at sea
Adventure Sailing Holidays
Climb aboard classic ships 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 and a holiday like no other. No experience needed, just a lust for adventure!
Featured Voyages
2021 Summertime Sailing in Scandinavia
- 3 July 2021, 8 days
- Vessel: Eye of the Wind
- Port: Denmark/Sweden
2021 Long Sailing Weekend in Devon
- 30 April 2021, 4 days
- Vessel: Pilgrim of Brixham
- Port: Devon
Crossing the Bay of Biscay to the Spanish Coast
- 8 October 2020, 9 days
- Vessel: Eye of the Wind
- Port: France/Spain
River Sailing Weekend
- 27 August 2021, 4 days
- Vessel: Reminder
- Port: Essex
2021 Spring Sailing in Cornwall
- 22 April 2021, 5 days
- Vessel: Pellew
- Port: Cornwall
2021 Devon Autumn Sailing Weekend
- 1 October 2021, 3 days
- Vessel: Pilgrim of Brixham
- Port: Devon
2021 Croatian Island Exploration
- 19 June 2021, 8 days
- Vessel: Kairós
- Port: Croatia
2021 Discovering Denmark under Sail
- 9 June 2021, 8 days
- Vessel: Eye of the Wind
- Port: Germany/Denmark
2021 Cornwall & Isles of Scilly Sailing
- 2 July 2021, 7 days
- Vessel: Pilgrim of Brixham
- Port: Cornwall
2021 Brixham Heritage Regatta Sailing Weekend
- 29 May 2021, 3 days
- Vessel: Escape
- Port: Devon
2021 Taster Sailing Weekend in Cornwall
- 9 April 2021, 3 days
- Vessel: Pellew
- Port: Cornwall
2021 Devon Sailing Weekend
- 15 May 2021, 2 days
- Vessel: Escape
- Port: Devon
Destinations
Our range of vessels enables us to offer several destinations all over the globe. Which adventure 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 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
“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
Latest from our Adventure Journal
Read up on life on board a tall ship! See what both skippers and customers have to say about sailing within our fleet.
10 June 2020
The history of Pilot Cutters and how these traditional boats are still sailing today
Read more
