Good for

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

Duration

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

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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

Sailing & Exploring Mull

Sailing & Exploring Mull

  • 11 May 2022, 7 days
  • Vessel: Pellew
  • Port: Scotland
£1,100 Details
Cruising the Hebrides; Skye and the Isles

Cruising the Hebrides; Skye and the Isles

  • 18 September 2021, 6 days
  • Vessel: Fleur de Lys
  • Port: Scotland
Was £1,500Now £1,350 Details
Sunshine Sailing & Island Hopping from Corfu

Sunshine Sailing & Island Hopping from Corfu

  • 25 June 2022, 7 days
  • Vessel: Circe
  • Port: Greece
£1,750 Details
Five Island Sailing in the Isles of Scilly

Five Island Sailing in the Isles of Scilly

  • 25 June 2022, 7 days
  • Vessel: Pettifox
  • Port: Isles of Scilly
£3,975 Details
Falmouth Classics & Sea Shanty Sailing

Falmouth Classics & Sea Shanty Sailing

  • 10 June 2022, 4 days
  • Vessel: Maybe
  • Port: Cornwall
£840 Details
Sailing & Whale Watching in the Hebrides

Sailing & Whale Watching in the Hebrides

  • 13 August 2022, 7 days
  • Vessel: Bessie Ellen
  • Port: Scotland
£1,105 Details
Sailing in Svalbard; Whalers Footsteps

Sailing in Svalbard; Whalers Footsteps

  • 25 June 2022, 11 days
  • Vessel: Noorderlicht
  • Port: Svalbard,Norway
£3,100 Details
Tall Ship Sailing in the Isles of Scilly

Tall Ship Sailing in the Isles of Scilly

  • 5 July 2022, 8 days
  • Vessel: Maybe
  • Port: Cornwall
£1,470 Details
Tall Ship Sailing Adventure

Tall Ship Sailing Adventure

  • 16 September 2021, 8 days
  • Vessel: Blue Clipper
  • Port: UK
£1,225 Details
Cruising the Hebrides; Skye and the Isles

Cruising the Hebrides; Skye and the Isles

  • 21 August 2021, 6 days
  • Vessel: Fleur de Lys
  • Port: Scotland
Was £1,500Now £1,350 Details
Falmouth Classics Sailing Weekend

Falmouth Classics Sailing Weekend

  • 9 June 2022, 5 days
  • Vessel: Pettifox
  • Port: Cornwall
£2,640 Details
Tall Ship Sailing in the Isles of Scilly

Tall Ship Sailing in the Isles of Scilly

  • 17 June 2022, 8 days
  • Vessel: Maybe
  • Port: Cornwall
£1,470 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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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’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.

Twister-distance-canary-islands
4 August 2021

When Is The Best Time To Sail The Canaries?

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Pellew classic pilot cutter sailing Cornwall
23 April 2021

Why A Classic Yacht Charter Offers The Perfect Holiday Opportunity in 2021

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Pellew Sailing
21 April 2021

COVID-19 FAQ's - Book with Confidence.

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Falmouth Classics Parade of sail
19 February 2021

Cornwall hosts the G7 & the Falmouth Classics

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View the whole log
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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