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

Tall Ship Sailing in the Outer Hebrides, Shiants & St Kilda

Tall Ship Sailing in the Outer Hebrides, Shiants & St Kilda

  • 1 June 2022, 10 days
  • Vessel: Blue Clipper
  • Port: Scotland
£2,205 Details
Isles of Scilly Sailing

Isles of Scilly Sailing

  • 26 August 2022, 7 days
  • Vessel: Agnes
  • Port: Cornwall
£1,100 Details
Cruising the Outer Hebrides; Barra & Uist Isles

Cruising the Outer Hebrides; Barra & Uist Isles

  • 9 July 2022, 6 days
  • Vessel: Fleur de Lys
  • Port: Scotland
£1,500 Details
Sailing & Exploring the Hebrides

Sailing & Exploring the Hebrides

  • 6 August 2022, 7 days
  • Vessel: Steady
  • Port: Scotland
£1,030 Details
Tall Ship Sailing in the Hebrides

Tall Ship Sailing in the Hebrides

  • 14 April 2022, 7 days
  • Vessel: Blue Clipper
  • Port: Scotland
£1,530 Details
Sunshine Sailing & Island Hopping from Corfu

Sunshine Sailing & Island Hopping from Corfu

  • 11 June 2022, 7 days
  • Vessel: Circe
  • Port: Greece
£1,750 Details
Sailing Adventure to the Isles of Scilly

Sailing Adventure to the Isles of Scilly

  • 21 June 2022, 8 days
  • Vessel: Pilgrim of Brixham
  • Port: Cornwall
£1,125 Details
Sailing in Norway; Lofoten & Ofoten

Sailing in Norway; Lofoten & Ofoten

  • 11 March 2023, 8 days
  • Vessel: Noorderlicht
  • Port: Norway
£1,890 Details
Taster Sailing in South Devon

Taster Sailing in South Devon

  • 23 August 2022, 2 days
  • Vessel: Pilgrim of Brixham
  • Port: Devon
£275 Details
Sailing & Exploring the River Tamar

Sailing & Exploring the River Tamar

  • 2 July 2022, 3 days
  • Vessel: Lynher
  • Port: Devon
£2,350 Details
Spring Sailing in Cornwall

Spring Sailing in Cornwall

  • 15 April 2022, 4 days
  • Vessel: Bessie Ellen
  • Port: Cornwall
£645 Details
Sailing & Exploring the River Tamar

Sailing & Exploring the River Tamar

  • 9 July 2022, 3 days
  • Vessel: Lynher
  • Port: Devon
£2,350 Details

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Destinations main page

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 main page

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 sailing in the Canary Islands
12 October 2021

Top Five Highlights of Sailing in Tenerife

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Twister-distance-canary-islands
4 August 2021

When Is The Best Time For A Sailing Holiday In 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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Fleet of traditional ships

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Why book with us?

Booking with VentureSail makes your sailing holiday fuss free.

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