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

Whale watching and wildlife in the Canary Islands

Whale watching and wildlife in the Canary Islands

  • Vessel: Twister
  • Port: San Miguel Marina, Tenerife
  • Where: The Canaries
  • Date: 13 January 2019
  • Duration: 7 days
Easter Weekend Hebridean Cruise

Easter Weekend Hebridean Cruise

  • Vessel: Zuza
  • Port: Oban
  • Where: Scotland
  • Date: 19 April 2019
  • Duration: 4 days
Bank Holiday Weekend Discovering Mull

Bank Holiday Weekend Discovering Mull

  • Vessel: Zuza
  • Port: Oban
  • Where: Scotland
  • Date: 3 May 2019
  • Duration: 4 days
Sailing the Devon and Cornish south coast to Falmouth

Sailing the Devon and Cornish south coast to Falmouth

  • Vessel: Escape
  • Port: Dartmouth
  • Where: Devon
  • Date: 10 June 2019
  • Duration: 4 days

Find more in the Voyage Finder

Dining On Board

Indulge in freshly prepared meals and home made snacks, life at sea can be hungry work after all!

Snap up an offer

If you're ready to pack your bags and go, these are the voyages for you. Take a look at our offers!

The Single Traveller

Our sailing holidays are ideal for solo travellers. Mix with like minded people and make new friends.

View Our Destinations

Looking for some 'must see' destinations? Then we have a voyage for you.

Destinations

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

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Classic sailing pilgrim

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 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 the adventure log

Read up on life on board a tall ship! See what both skippers and customers have to say about sailing within our fleet.

Hiker on the Isle of Skye
14 November 2018

Sailing around the Isle of Skye

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Hirta and dun at St. Kilda
14 November 2018

Sailing to St. Kilda

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The Isle of Skye
30 October 2018

The Lure of Scotland : Helen Walker and her love of the Scottish Isles

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Douarnenez festival of the sea harbourside
2 July 2018

The Douarnenez Maritime Festival Experience

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Join our fleet

See how much of a difference joining us can make to your sailing holiday business...

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Why book with us?

How VentureSail makes your holiday fuss free so all you need do is enjoy your venture aboard a classic ship.

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