classic holidays at sea

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 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 and a holiday like no other. No experience needed, just a lust for adventure!

Looking for a 2020 summer get-away? Why not book a “Boat Bubble Holiday” for an all-inclusive sailing adventure in Devon and Cornwall. Read more about our 2020 sailing options here >

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Featured Voyages

Sailing the Maltese Islands

Sailing the Maltese Islands

  • 24 October 2020, 7 days
  • Vessel: Chronos
  • Port: Malta
£2,150 Details
Sailing & Island Hopping in Cape Verde

Sailing & Island Hopping in Cape Verde

  • 18 January 2021, 12 days
  • Vessel: Oosterschelde
  • Port: Cape Verde
£1,530 Details
2021 Long Sailing Weekend in Devon

2021 Long Sailing Weekend in Devon

  • 30 April 2021, 4 days
  • Vessel: Pilgrim of Brixham
  • Port: Devon
£285 Details
2021 Easter Sailing in Cornwall

2021 Easter Sailing in Cornwall

  • 2 April 2021, 4 days
  • Vessel: Pellew
  • Port: Cornwall
£525 Details
2021 Sailing & Exploring the Isles of Scilly

2021 Sailing & Exploring the Isles of Scilly

  • 29 April 2021, 7 days
  • Vessel: Pellew
  • Port: Cornwall
£1,050 Details
2021 Cornwall & Isles of Scilly Sailing

2021 Cornwall & Isles of Scilly Sailing

  • 24 June 2021, 7 days
  • Vessel: Pilgrim of Brixham
  • Port: Cornwall
£945 Details
2021 Sailing & Exploring the Hebrides

2021 Sailing & Exploring the Hebrides

  • 13 June 2021, 7 days
  • Vessel: Pellew
  • Port: Scotland
£1,020 Details
Sailing & Whale Watching in Norway

Sailing & Whale Watching in Norway

  • 13 February 2021, 8 days
  • Vessel: Noorderlicht
  • Port: Norway
£1,690 Details
Luxury Sailing from Corfu

Luxury Sailing from Corfu

  • 24 July 2021, 8 days
  • Vessel: Chronos
  • Port: Greece
£2,820 Details
2021 Sailing & Exploring the Isles of Scilly

2021 Sailing & Exploring the Isles of Scilly

  • 11 May 2021, 7 days
  • Vessel: Agnes
  • Port: Cornwall
£925 Details
2021 Easter Sailing in Italy & Croatia

2021 Easter Sailing in Italy & Croatia

  • 2 April 2021, 8 days
  • Vessel: Kairós
  • Port: Italy
£2,165 Details
2021 Sailing & Exploring the Hebrides

2021 Sailing & Exploring the Hebrides

  • 21 June 2021, 10 days
  • Vessel: Pellew
  • Port: Scotland
£1,400 Details

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Destinations

Our range of vessels enables us to offer several destinations all over the globe. Which adventure 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.

Pellew Sailing
8 July 2020

COVID-19 What you need to know

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Agnes sailing
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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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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