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 sailing holiday. VentureSail offers 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. There’s a huge choice across the fleet, from private ensuite cabins on luxury yachts to shared quarters on a tall ship. So much of the world is waiting to be explored; discover it under sail.
Featured Sailing Holidays
Show pricesLuxury Saronic Island Sailing Holiday in Greece
- 28 December 2024, 8 days
- Vessel: Kairós
- Port: Greece
- Board type: Full Board
Tall Ship Sailing from Naples to Sardinia
- 7 June 2025, 16 days
- Vessel: Florette
- Port: Italy
- Board type: Half Board
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Our range of vessels enables us to offer several destinations all over the world. Which sailing holiday will you choose?
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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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Be inspired to discover the world under sail! Read our latest journals below.