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

Luxury Yacht Sailing in the Grenadines

Luxury Yacht Sailing in the Grenadines

  • 8 February 2023, 10 days
  • Vessel: Skyelark
  • Port: St Lucia, Caribbean
£2,400.00 Details
Mediterranean Sailing in the Lipari Islands

Mediterranean Sailing in the Lipari Islands

  • 22 October 2022, 8 days
  • Vessel: Kairós
  • Port: Sicily, Italy
£1,795.00 Details
Scandinavian Tall Ship Sailing

Scandinavian Tall Ship Sailing

  • 29 July 2023, 8 days
  • Vessel: Eye of the Wind
  • Port: Sweden/Germany
£1,885.00 Details
Tall Ship Sailing Adventure; Spain to Portugal

Tall Ship Sailing Adventure; Spain to Portugal

  • 11 October 2023, 8 days
  • Vessel: Blue Clipper
  • Port: Spain, Portugal
£1,995.00 Details
Sailing the Caledonian Canal and Great Glen Way

Sailing the Caledonian Canal and Great Glen Way

  • 3 May 2023, 7 days
  • Vessel: Steady
  • Port: Inverness, Scotland
£1,130.00 Details
Classic Sailing in the Inner Hebrides

Classic Sailing in the Inner Hebrides

  • 18 June 2023, 6 days
  • Vessel: Maybe
  • Port: Oban, Scotland
£1,210.00 Details
Luxury Yacht Sailing in the Grenadines

Luxury Yacht Sailing in the Grenadines

  • 28 February 2023, 10 days
  • Vessel: Skyelark
  • Port: St Lucia, Caribbean
£2,400.00 Details
Tall Ship Summer Sailing in the Hebrides

Tall Ship Summer Sailing in the Hebrides

  • 25 July 2023, 6 days
  • Vessel: Blue Clipper
  • Port: Oban, Scotland
£1,490.00 Details
Sailing & Wild Swimming in the Hebrides

Sailing & Wild Swimming in the Hebrides

  • 15 September 2023, 3 days
  • Vessel: Stravaigin
  • Port: Oban, Scotland
£525.00 Details
Sailing & Walking in the Hebrides

Sailing & Walking in the Hebrides

  • 9 August 2023, 10 days
  • Vessel: Steady
  • Port: Oban, Scotland
£1,550.00 Details
Tall Ship Sailing in the Inner Hebrides

Tall Ship Sailing in the Inner Hebrides

  • 30 June 2023, 6 days
  • Vessel: Blue Clipper
  • Port: Oban, Scotland
£1,490.00 Details
Hebridean Exploring around Mull & the Isles

Hebridean Exploring around Mull & the Isles

  • 24 June 2023, 7 days
  • Vessel: Bessie Ellen
  • Port: Oban, Scotland
£1,250.00 Details

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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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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’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

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.

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Our Top Five Family Friendly Sailing Holidays

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Richard Collett on Grayhound

Life on a Cornish Lugger - Sailing in the foosteps of Smugglers

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Why should you choose a skippered sailing holiday charter in Greece?

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Falmouth Classics Parade of sail

Why you should join us for the Falmouth International Sea Shanty Festival!

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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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