sailing holidays for all

Good for

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

Duration

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

Options

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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

Devon Autumn Sailing Weekend

Devon Autumn Sailing Weekend

  • 1 October 2021, 3 days
  • Vessel: Pilgrim of Brixham
  • Port: Devon
£275 Details
Falmouth Classics & Sea Shanty Weekend

Falmouth Classics & Sea Shanty Weekend

  • 11 June 2021, 4 days
  • Vessel: Escape
  • Port: Cornwall
£490 Details
Caribbean Christmas Sailing St Martin to Tortola BVI

Caribbean Christmas Sailing St Martin to Tortola BVI

  • 22 December 2021, 7 days
  • Vessel: Chronos
  • Port: Caribbean
£2,350 Details
Sailing & Exploring the River Tamar

Sailing & Exploring the River Tamar

  • 29 May 2021, 3 days
  • Vessel: Lynher
  • Port: Devon
£350 Details
Devon Spring Sailing Weekend

Devon Spring Sailing Weekend

  • 24 April 2021, 3 days
  • Vessel: Pilgrim of Brixham
  • Port: Devon
£275 Details
Sailing & Exploring the Hebrides

Sailing & Exploring the Hebrides

  • 13 July 2021, 7 days
  • Vessel: Pellew
  • Port: Scotland
Was £1,020Now £918 Details
Devon Sailing Weekend

Devon Sailing Weekend

  • 15 May 2021, 2 days
  • Vessel: Escape
  • Port: Devon
£260 Details
Sailing the Caledonian Canal

Sailing the Caledonian Canal

  • 31 August 2021, 4 days
  • Vessel: Bessie Ellen
  • Port: Scotland
£680 Details
Sailing and Walking in the Hebrides

Sailing and Walking in the Hebrides

  • 17 August 2021, 8 days
  • Vessel: Steady
  • Port: Scotland
Was £1,090Now £981 Details
Summertime Sailing in Scandinavia

Summertime Sailing in Scandinavia

  • 3 July 2021, 8 days
  • Vessel: Eye of the Wind
  • Port: Denmark/Sweden
£1,745 Details
On course to Copenhagen

On course to Copenhagen

  • 29 June 2021, 5 days
  • Vessel: Eye of the Wind
  • Port: Germany/Denmark
£1,040 Details
Easter Sailing in Italy & Croatia

Easter Sailing in Italy & Croatia

  • 2 April 2021, 8 days
  • Vessel: Kairós
  • Port: Italy
£2,165 Details

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BLACK FRIDAY SALE

Enjoy 10% off a selection of 2021 sailing holidays with some of our beautiful vessels. Hurry, offers end on the 6th December!

VIEW ALL BLACK FRIDAY OFFERS >

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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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 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.

Agnes under sail classic boat sailing Cornwall
10 June 2020

The history of Pilot Cutters and how these traditional boats are still sailing today

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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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Fleet of traditional ships

Join our fleet

We can make to your boat charter business plain sailing.

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Why book with us?

Booking with VentureSail makes your sailing holiday fuss free.

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