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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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Ski & Sail in the Lofoten Islands

12 March 2025, 5 days
Vessel: Humla
Port: Norway
Board type: Full Board

£2,215.00€2,547.25 Details

Svalbard Sailing Explorer: Arctic Wildlife Expedition

17 July 2026, 8 days
Vessel: Valiente
Port: Svalbard, Norway
Board type: Full Board

£3,300.00€3,795.00 Details

Hebridean Sailing & Wildlife Encounters Mull, Skye and the Small Isles

3 August 2025, 7 days
Vessel: Zuza
Port: Oban, Scotland
Board type: Full Board

£1,565.00€1,799.75 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

Antarctica Expedition: From Chile to Antarctica

23 February 2025, 22 days
Vessel: Tecla
Port: Chile/Antarctica
Board type: Full Board

£8,585.00€9,900.00 Details

Luxury Yacht Sailing & Croatian Island Hopping

19 July 2025, 8 days
Vessel: Kairós
Port: Croatia
Board type: Full Board

£3,080.00€3,550.00 Details

Tall Ship Sailing in the Norwegian Fjords

23 July 2025, 8 days
Vessel: Bessie Ellen
Port: Norway
Board type: Full Board

£1,720.00€1,978.00 Details

Tall Ship Sailing & Island Hopping in Cape Verde

22 January 2025, 12 days
Vessel: Morgenster
Port: Cape Verde
Board type: Full Board

£1,540.00€1,745.00 Details

Double Leg!

Tall Ship Sailing from Naples to Sardinia

7 June 2025, 16 days
Vessel: Florette
Port: Italy
Board type: Half Board

£2,215.00€2,580.00 Details

Traditional Taster Sailing Short Break in Cornwall

19 September 2025, 4 days
Vessel: Pellew
Port: Falmouth, Cornwall
Board type: Full Board

£655.00€753.25 Details

Caribbean Christmas Onboard a Tall Ship: Barbados to St Lucia

20 December 2024, 8 days
Vessel: Blue Clipper
Port: Barbados/St Lucia
Board type: Full Board

£2,100.00€2,465.00 Details

Sailing the remote Ring of Fire in Indonesia

25 June 2025, 10 days
Vessel: Ombak Putih
Port: Indonesia
Board type: Full Board

£4,875.00€5,606.25 Details

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Special offers

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Eco-Tourism Pledge

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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