sailing holidays for all

Good for

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

Duration

  • 1 day
  • 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 in Norway; Lofoten & Ofoten

Sailing in Norway; Lofoten & Ofoten

  • 2 April 2022, 8 days
  • Vessel: Noorderlicht
  • Port: Norway
£1,550 Details
Sailing in Cornwall & the Scillies

Sailing in Cornwall & the Scillies

  • 9 August 2021, 7 days
  • Vessel: Agnes
  • Port: Cornwall
£925 Details
Sailing & Volcano Adventure in the Aeolian Islands

Sailing & Volcano Adventure in the Aeolian Islands

  • 21 August 2021, 8 days
  • Vessel: Florette
  • Port: Italy
£990 Details
Sailing in Norway; Lofoten & Ofoten

Sailing in Norway; Lofoten & Ofoten

  • 12 March 2022, 8 days
  • Vessel: Noorderlicht
  • Port: Norway
£1,550 Details
Canary Island Exploring under Sail

Canary Island Exploring under Sail

  • 6 December 2021, 7 days
  • Vessel: Twister
  • Port: The Canaries
£1,100 Details
Scandinavian Sailing from Sweden to Denmark

Scandinavian Sailing from Sweden to Denmark

  • 7 August 2021, 8 days
  • Vessel: Eye of the Wind
  • Port: Sweden/Denmark
£1,745 Details
Tall Ship Sailing in Cornwall

Tall Ship Sailing in Cornwall

  • 9 August 2021, 5 days
  • Vessel: Maybe
  • Port: Cornwall
£850 Details
Sailing in Cornwall

Sailing in Cornwall

  • 1 October 2021, 4 days
  • Vessel: Eda Frandsen
  • Port: Cornwall
£510 Details
Sailing in Svalbard

Sailing in Svalbard

  • 19 August 2022, 9 days
  • Vessel: Noorderlicht
  • Port: Svalbard,Norway
£2,315 Details
Devon Autumn Sailing Weekend

Devon Autumn Sailing Weekend

  • 1 October 2021, 3 days
  • Vessel: Pilgrim of Brixham
  • Port: Devon
£275 Details
Caribbean New Year Sailing in Antigua & Barbuda

Caribbean New Year Sailing in Antigua & Barbuda

  • 28 December 2021, 11 days
  • Vessel: Chronos
  • Port: Caribbean
£3,300 Details
Sailing & Exploring Svalbard

Sailing & Exploring Svalbard

  • 5 July 2022, 16 days
  • Vessel: Noorderlicht
  • Port: Svalbard,Norway
£4,835 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.

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
31 March 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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Sailing guide to Cornwall Helford
15 January 2021

A seasonal guide to sailing in Cornwall

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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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