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
- 12 June 2024, 7 days
- Vessel: Stravaigin
- Port: Oban, Scotland
Sailing the Indonesian Wonders; Whale Sharks, Dragons & Coral Reefs
- 3 June 2023, 8 days
- Vessel: Ombak Putih
- Port: Indonesia
Luxury Classic Yacht Sailing from Corfu
- 22 June 2024, 8 days
- Vessel: Kairós
- Port: Corfu, Greece
Taster Sailing in South Devon
- 15 August 2023, 3 days
- Vessel: Pilgrim of Brixham
- Port: Brixham, Devon
Exploring the Isles of Scilly With Pilot Cutter Pellew
- 30 August 2023, 7 days
- Vessel: Pellew
- Port: Falmouth, Cornwall
Luxury Sailing from Sicily
- 6 September 2023, 10 days
- Vessel: Kairós
- Port: Sicily, Italy
Luxury Sailing around the Aeolian Islands
- 5 October 2024, 8 days
- Vessel: Kairós
- Port: Sicily, Italy
Classic Sailing in the Isles of Scilly
- 3 July 2023, 7 days
- Vessel: Maybe
- Port: Penzance, Cornwall
Luxury Classic Yacht Sailing from Corfu
- 3 June 2023, 8 days
- Vessel: Kairós
- Port: Corfu, Greece
Private Charter in the Lofoten Islands
- 8 September 2024, 6 days
- Vessel: Stella Oceana
- Port: Norway
Private Charter in Norway; Arctic Circle Sailing
- 13 July 2023, 4 days
- Vessel: Stella Oceana
- Port: Norway
Overnight Tall Ship Sailing in Devon
- 22 April 2023, 2 days
- Vessel: Pilgrim of Brixham
- Port: Brixham, Devon
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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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.
View FleetLatest from our Adventure Journal
Be inspired to discover the world under sail! Read our latest journals below.
Our Eco-Tourism Pledge
Sustainable tourism is at the heart of VentureSail, read our pledge.
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Join our fleet
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