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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

Luxury Sailing & Island Hopping from Santorini

21 September 2024, 8 days
Vessel: Rhea
Port: Santorini, Greece

£2,900.00 Details

Luxury Wellness Sailing in Sardinia & Corsica

1 July 2023, 8 days
Vessel: Agave
Port: Sardinia, Italy

£2,200.00 Details

Luxury Sailing in Sardinia

26 August 2023, 8 days
Vessel: Chronos
Port: Sardinia, Italy

£3,035.00 Details

Luxury Sailing & Island Hopping in Italy

29 July 2023, 8 days
Vessel: Chronos
Port: Italy

£3,020.00 Details

LUXURY SAILING AROUND THE AEOLIAN ISLANDS

14 September 2024, 11 days
Vessel: Kairós
Port: Sicily, Italy

£3,750.00 Details

Sailing & Exploring the Hebrides

20 August 2023, 9 days
Vessel: Cherokee
Port: Hebrides, Scotland

£1,265.00 Details

Sailing Expedition in Svalbard; 16 day circumnavigation

15 August 2024, 16 days
Vessel: Noorderlicht
Port: Svalbard, Norway

£5,700.00 Details

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

26 August 2023, 8 days
Vessel: Ombak Putih
Port: Indonesia

£3,765.00 Details

Sunshine Sailing in the Saronic Islands, Greece

21 October 2023, 8 days
Vessel: Zorba
Port: Saronic Islands, Greece

£895.00 Details

Sunshine Skippered Sailing in the Cyclades, Greece

26 August 2023, 8 days
Vessel: Zorba
Port: Naxos, Greece

£895.00 Details

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

13 June 2023, 8 days
Vessel: Katharina
Port: Indonesia

£3,765.00 Details

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

26 July 2023, 8 days
Vessel: Ombak Putih
Port: Indonesia

£3,765.00 Details

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Brochure Download

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Special offers

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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.

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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