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

Arctic Circle sailing; Svalbard Expedition

1 July 2023, 8 days
Vessel: Valiente
Port: Svalbard, Norway

£3,295.00 Details

Private Charter in the Lofoten Islands

30 June 2024, 6 days
Vessel: Stella Oceana
Port: Norway

On request Details

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

16 May 2023, 8 days
Vessel: Katharina
Port: Indonesia

£3,765.00 Details

Sailing & Exploring Isfjorden, Svalbard

16 September 2023, 8 days
Vessel: Noorderlicht
Port: Svalbard, Norway

£2,495.00 Details

Luxury Classic Yacht Sailing from Corfu

3 June 2023, 8 days
Vessel: Kairós
Port: Corfu, Greece

£2,785.00 Details

Expedition Sailing; Svalbard, Greenland & Iceland

24 August 2023, 13 days
Vessel: Valiente
Port: Svalbard/Iceland

£4,920.00 Details

Sunshine Skippered Sailing in the Cyclades, Greece

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

£895.00 Details

Expedition Sailing; Scotland to Norway

23 September 2023, 15 days
Vessel: Valiente
Port: Scotland/Norway

£3,975.00 Details

Private Charter in the Lofoten Islands

4 August 2024, 6 days
Vessel: Stella Oceana
Port: Norway

On request Details

Luxury Sailing & Island Hopping in Italy

10 June 2023, 8 days
Vessel: Chronos
Port: Italy

£2,710.00 Details

Sailing Holiday through the Cyclades, Greece

2 September 2023, 8 days
Vessel: Zorba
Port: Naxos, Greece

£895.00 Details

Sailing & Walking in the Hebrides

20 May 2023, 10 days
Vessel: Steady
Port: Oban, Scotland

£1,550.00 Details

Search for more in our Voyage Finder

Destinations

Our range of vessels enables us to offer several destinations all over the world. Which sailing holiday will you choose?

View Destinations

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 Fleet

“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