Good for

  • Cruising
  • Exploration
  • Ocean passages
  • Training
  • Wildlife
  • Winter sun
  • Sun
  • Racing

Duration

  • 1 day
  • 2 - 6 days
  • 1 week +
  • 2 weeks +

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

River Sailing Weekend

River Sailing Weekend

  • 18 July 2020, 2 days
  • Vessel: Reminder
  • Port: Essex
Sailing around The Inner Hebrides

Sailing around The Inner Hebrides

  • 7 July 2020, 8 days
  • Vessel: Cherokee
  • Port: Scotland
Atlantic Sailing from Gran Canaria to the Caribbean

Atlantic Sailing from Gran Canaria to the Caribbean

  • 21 November 2020, 32 days
  • Vessel: Blue Clipper
  • Port: Canary Islands/Caribbean
2021 Sunshine Sailing & Island Hopping from Corfu

2021 Sunshine Sailing & Island Hopping from Corfu

  • 6 June 2021, 7 days
  • Vessel: Circe
  • Port: Greece

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. Meet like-minded people and make new friends.

Give the Gift of Sailing

Know someone who would love one of our holidays? Why not buy them a gift voucher?

Destinations

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

View destinations
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.

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 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.

11 May 2020

COVID-19 What you need to know

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Norway Fjord Stranda
17 February 2020

Why you should choose a sailing holiday in Norway

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Gin and tonic on board Bessie Ellen in Scotland
1 February 2020

Jump Aboard A Sailing Holiday In Scotland On The Bessie Ellen

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Scotland Isle of Bute
1 February 2020

Sailing adventures and foodie experiences in the Firth of Clyde, Scotland

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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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