Adventure Sailing Holidays

Climb aboard classic ships, luxury yachts or adventure vessels and explore a host of destinations as you’ve never seen them before. Let our fleet of boats give you an authentic taste of life under sail as you learn the ropes and experience a sailing holiday like no other. All our voyages are fully crewed so there’s no sailing experience needed to join a sailing holiday adventure!

View all voyages

Featured Sailing Holidays

Bank Holiday Cruising in the Small Isles

Bank Holiday Cruising in the Small Isles

  • 26 August 2023, 4 days
  • Vessel: Fleur de Lys
  • Port: Mallaig, Scotland
£825.00 Details
Sailing the Hebrides with Skyelark

Sailing the Hebrides with Skyelark

  • 23 July 2022, 8 days
  • Vessel: Skyelark
  • Port: Oban, Scotland
£2,000.00 Details
Sailing & Exploring the Cyclades in Greece

Sailing & Exploring the Cyclades in Greece

  • 19 August 2023, 8 days
  • Vessel: Zorba
  • Port: Naxos, Greece
£895.00 Details
Tall Ship Summer Sailing in the Hebrides

Tall Ship Summer Sailing in the Hebrides

  • 25 July 2023, 6 days
  • Vessel: Blue Clipper
  • Port: Oban, Scotland
£1,490.00 Details
Sailing the Outer Hebrides

Sailing the Outer Hebrides

  • 20 August 2022, 7 days
  • Vessel: Bessie Ellen
  • Port: Oban, Scotland
£1,105.00 Details
Mediterranean Sailing in the Lipari Islands

Mediterranean Sailing in the Lipari Islands

  • 22 October 2022, 8 days
  • Vessel: Kairós
  • Port: Sicily, Italy
£1,795.00 Details
Tall Ship Taster Sailing in Scotland

Tall Ship Taster Sailing in Scotland

  • 13 June 2023, 4 days
  • Vessel: Blue Clipper
  • Port: Oban, Scotland
£870.00 Details
Sailing & Exploring the Saronic Islands in Greece

Sailing & Exploring the Saronic Islands in Greece

  • 1 July 2023, 8 days
  • Vessel: Zorba
  • Port: Athens, Greece
£895.00 Details
Yacht Charter Sailing in Cornwall

Yacht Charter Sailing in Cornwall

  • 14 July 2022, 4 days
  • Vessel: Unity
  • Port: Falmouth, Cornwall
£650.00 Details
Tall Ship Sailing Skye & the Small Isles

Tall Ship Sailing Skye & the Small Isles

  • 10 August 2023, 7 days
  • Vessel: Blue Clipper
  • Port: Mallaig, Scotland
£1,760.00 Details
New Year Sailing in Cape Verde

New Year Sailing in Cape Verde

  • 28 December 2022, 11 days
  • Vessel: Kairós
  • Port: Cape Verde
£3,635.00 Details
Sailing in Greece; Exploring the Saronic Islands

Sailing in Greece; Exploring the Saronic Islands

  • 22 October 2022, 8 days
  • Vessel: Zorba
  • Port: Athens, Greece
£835.00 Details

Search for more in our Voyage Finder

Destinations main page

Destinations

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

View Destinations
Our Fleet main page

Our Fleet

With vessels of all sizes and each with a unique history and construction, 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
“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
“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
“I thoroughly enjoyed reliving my youth onboard Bessie Ellen. We came from Cornwall to Oban on this beautiful ship with Skipper Nikki and her brilliant crew. Great hands on sailing, relaxed atmosphere and fabulous food. A true get away.”Kate Smith, Bessie Ellen Guest

Latest from our Adventure Journal

Read up on life on board a tall ship! See what both skippers and customers have to say about sailing within our fleet.

Richard Collett on Grayhound
9 June 2022

Life on a Cornish Lugger - Sailing in the foosteps of Smugglers

Read more
Zorba greece Saronic island sailing
30 May 2022

Why should you choose a skippered sailing holiday charter in Greece?

Read more
Falmouth Classics Parade of sail
14 May 2022

Why you should join us for the Falmouth International Sea Shanty Festival!

Read more
Zorba anchored Cyclades
19 April 2022

Sailing in the Cyclades Islands, Greece

Read more
View the whole log
Fleet of traditional ships

Join our fleet

We can make to your boat charter business plain sailing.

Read more

Why book with us?

Booking with VentureSail makes your sailing holiday fuss free.

Read more