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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

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Indonesian Guided Wildlife Watching Holiday: Birds of Paradise & Whale Sharks

5 December 2026, 10 days
Vessel: Ombak Putih
Port: West Papau, Indonesia
Board type: Full Board

£6,310.00€7,256.50 Details

Luxury Private Catamaran Charter in Croatia

20 September 2025, 8 days
Vessel: Agave
Port: Croatia
Board type: Half Board

£2,080.00€2,392.00 Details

Remote Islands & Wonderful Wildlife: Sailing the Hebrides

16 June 2025, 11 days
Vessel: Steady
Port: Oban, Scotland
Board type: Full Board

£1,900.00€2,150.00 Details

New Year Break Offer

Luxury Saronic Island Sailing Holiday in Greece

28 December 2024, 8 days
Vessel: Kairós
Port: Greece
Board type: Full Board

Was £2,060.00€2,300.00Now £1,545.00€1,725.00 Details

Guided Hiking & Sailing in the Aeolian Islands

3 May 2025, 8 days
Vessel: Florette
Port: Vibo Valentia, Italy
Board type: Half Board

£1,795.00€2,080.00 Details

Sailing The Indonesian Wonders; Whale Sharks, Corals & Dragons

20 August 2025, 9 days
Vessel: Ombak Putih
Port: Komodo, Indonesia
Board type: Full Board

£4,320.00€4,968.00 Details

Guided Wildlife Watching & Whale Sharks in Indonesia

5 October 2026, 10 days
Vessel: Katharina
Port: West Papau, Indonesia
Board type: Full Board

£6,310.00€7,256.50 Details

Scottish Island Hopping & Tall Ship Sailing in the Hebrides

27 June 2025, 6 days
Vessel: Blue Clipper
Port: Oban, Scotland
Board type: Full Board

£1,820.00€2,093.00 Details

Adventure Sailing in the Fjords of Greenland

11 July 2025, 8 days
Vessel: Valiente
Port: Greenland
Board type: Full Board

£3,855.00€4,433.25 Details

Indonesian Guided Wildlife Watching Holiday: Birds of Paradise & Whale Sharks

5 December 2024, 10 days
Vessel: Ombak Putih
Port: West Papau, Indonesia
Board type: Full Board

£6,485.00€7,457.75 Details

Tall Ship Sailing in Denmark; Svendborg to Nyborg

28 July 2025, 5 days
Vessel: Aron of Svendborg
Port: Funen, Denmark
Board type: Full Board

£870.00€1,000.50 Details

Sailing The Indonesian Wonders; Whale Sharks, Corals & Dragons

6 July 2026, 9 days
Vessel: Ombak Putih
Port: Komodo, Indonesia
Board type: Full Board

£4,555.00€5,238.25 Details

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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