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Adventure Sailing Holidays

The Earth is two-thirds water, yet we spend most of our life on land. So cast off, take the plunge and discover the life-changing freedom of a holiday under sail. VentureSail offer 400+ adventures to amazing destinations on unusual boats, run by passionate crews. Get hands on and learn the ropes, or relax on deck and enjoy the journey wherever it takes you. Delicious food is freshly prepared for you each day, and a good night’s sleep in your comfy berth is guaranteed. There’s a huge choice across the fleet, from private ensuite cabins on luxury yachts to shared quarters on a classic tall ship. There’s so much of the world waiting to be explored, discover it under sail.

Featured Sailing Holidays

Guided Wild Swimming & Sailing in Scotland

Guided Wild Swimming & Sailing in Scotland

  • 12 June 2024, 7 days
  • Vessel: Stravaigin
  • Port: Oban, Scotland
£1,300.00 Details
Sailing the Indonesian Wonders; Whale Sharks, Dragons & Coral Reefs

Sailing the Indonesian Wonders; Whale Sharks, Dragons & Coral Reefs

  • 3 June 2023, 8 days
  • Vessel: Ombak Putih
  • Port: Indonesia
£3,765.00 Details
Luxury Classic Yacht Sailing from Corfu

Luxury Classic Yacht Sailing from Corfu

  • 22 June 2024, 8 days
  • Vessel: Kairós
  • Port: Corfu, Greece
£2,760.00 Details
Taster Sailing in South Devon

Taster Sailing in South Devon

  • 15 August 2023, 3 days
  • Vessel: Pilgrim of Brixham
  • Port: Brixham, Devon
£435.00 Details
Exploring the Isles of Scilly With Pilot Cutter Pellew

Exploring the Isles of Scilly With Pilot Cutter Pellew

  • 30 August 2023, 7 days
  • Vessel: Pellew
  • Port: Falmouth, Cornwall
£1,295.00 Details
Luxury Sailing from Sicily

Luxury Sailing from Sicily

  • 6 September 2023, 10 days
  • Vessel: Kairós
  • Port: Sicily, Italy
£3,870.00 Details
Luxury Sailing around the Aeolian Islands

Luxury Sailing around the Aeolian Islands

  • 5 October 2024, 8 days
  • Vessel: Kairós
  • Port: Sicily, Italy
£2,500.00 Details
Classic Sailing in the Isles of Scilly

Classic Sailing in the Isles of Scilly

  • 3 July 2023, 7 days
  • Vessel: Maybe
  • Port: Penzance, Cornwall
£1,455.00 Details
Luxury Classic Yacht Sailing from Corfu

Luxury Classic Yacht Sailing from Corfu

  • 3 June 2023, 8 days
  • Vessel: Kairós
  • Port: Corfu, Greece
£2,785.00 Details
Private Charter in the Lofoten Islands

Private Charter in the Lofoten Islands

  • 8 September 2024, 6 days
  • Vessel: Stella Oceana
  • Port: Norway
On request Details
Private Charter in Norway; Arctic Circle Sailing

Private Charter in Norway; Arctic Circle Sailing

  • 13 July 2023, 4 days
  • Vessel: Stella Oceana
  • Port: Norway
On request Details
Overnight Tall Ship Sailing in Devon

Overnight Tall Ship Sailing in Devon

  • 22 April 2023, 2 days
  • Vessel: Pilgrim of Brixham
  • Port: Brixham, Devon
£265.00 Details

Search for more in our Voyage Finder

Indonesia Raja Ampat anchored

Destinations

Our range of vessels enables us to offer several destinations all over the world. Which sailing holiday will you choose?

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Bessie Ellen and Agnes Sailing

Our Fleet

Take a look at our unique fleet. From classic boats to luxury yachts and expedition vessels, 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
"A sailing holiday is more than a break, it’s a real adventure – you never know what you might encounter. I was lucky enough to have wonderful, friendly passengers and crew and good weather for the most part, while making memories that will stay with me forever."Alex Fisher, Coast Magazine
“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
“Agnes is a boat for those who dream of the golden age of sail and want to taste it for themselves. Sure, there are easier and faster ways to get from Falmouth to Fowey and back, but certainly none as romantic.”Wyl Menmuir, The Guardian
"I was sad to leave the sea salt behind. But not only had I found an appreciation for the skills of mariners and sailors, but I was satisfied that the voyage had been a sustainable one."Richard Collett, Travel Tramp
“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

Latest from our Adventure Journal

Be inspired to discover the world under sail! Read our latest journals below.

Italy Sardinia Madallena archipelago

Discover La Maddalena: The Hidden Gem of Sardinia

Read more
Copenhagen Denmark colourful houses on the Nyhavn

Our top 5 places to visit in Denmark on a sailing holiday 

Read more
Indonesia Sumbawa boat builders

The History of Indonesian Pinisi Boats

Read more
Aerial View of Petit St Vincent in the Caribbean

Low Carbon Luxury Travel

Read more
View our Adventure Journal
CHRONOS guests bow net

Brochure Download

Want a brief overview of what we offer? Download our brochure.

Download here
CWT cornwall dolphin

Our Eco-Tourism Pledge

Sustainable tourism is at the heart of VentureSail, read our pledge.

Read our pledge
Norway Lyngen Alps Northern Lights jpg

Join our fleet

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Redruth
Cornwall
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Edinburgh
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  • Search all Voyages
  • Destinations
    • UK
      • Channel Islands
      • Cornwall
      • Devon
      • Isles of Scilly
      • Scotland & the Hebrides
      • Scotland – St Kilda
      • Scotland – Firth of Clyde
      • Back
    • Europe
      • Canary Islands
      • Corfu
      • Croatia
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      • Back
    • Rest of the World
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      • Back
    • Back
  • Fleet
    • Luxury Yachts
      • Agave
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      • Ombak Putih
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    • Expedition Boats
      • Cherokee
      • Steady
      • Stella Oceana
      • Stravaigin
      • Valiente
      • Zorba
      • Zuza
      • Back
    • Traditional Vessels
      • Agnes
      • Aron
      • Bessie Ellen
      • Blue Clipper
      • Grayhound
      • Escape
      • Eye of the Wind
      • Florette
      • Flying Dutchman
      • Iris
      • Maybe
      • Noorderlicht
      • Oosterschelde
      • Pellew
      • Pilgrim of Brixham
      • Back
    • SAILING CLASSICS UK
    • See All Our Fleet
    • Back
  • Adventures
    • Expedition Adventure
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    • Relax & Sunshine
    • Ski and Sail
    • Snow & Ice
    • Weekend Taster Sails
    • Back
  • Offers
  • Sailing with us
    • FAQs
    • Solo Travelling
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    • Dining Aboard
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    • Contact us
    • Corporate Hire
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    • Eco Tourism Pledge
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