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Scottish Sailing Holidays

Book your activity holiday with Europe's No.1 Adventure Travel Company - Wilderness Scotland

Discover the joys of sailing holidays in Scotland as you explore the west coast and islands by yacht.

We sail and explore by day and stay on the yachts overnight, often moored in remote wilderness anchorages.

These trips combine sailing and gentle walking as a great way to explore Scotland’s islands and coast. Although we have outline itineraries, these are flexible, allowing you to follow the best weather and winds.

Our classic sailing yacht is a beautifully restored traditional wooden gaff cutter, so provides a memorable way to island hop. Our expert skipper will have you at the helm in no time, while the first mate / chef will soon be your best friend! On trips which involve walking on the islands, we also have an expert and qualified walking guide on board.

We also arrange private charters so you can build the perfect sailing journey. We have access to a wide range of yachts for private charter, including a luxury Swan 68 for the ultimate sailing charter in Scotland. Visit our tailor made page for details and to contact us for a private charter.

Trip Reviews

Customer Kudos

Every client receives a feedback survey when they return from their guided, self guided or tailor made holiday with us.

Once completed the review is published on our website just as soon as our database updates. The little touches and details are important to us and where issues are raised we make positive changes to our trips to improve your experience.

That's why we read each of our client's reviews and although we don't respond to all of them, if it's glowing feedback then we get the satisfaction of helping to make your holidays truly memorable.

Sailing and Walking - Knoydart, Skye & The Small Isles
Overall well up to Wilderness Scotland's high sstandards.

Caroline Taylor


Sailing and Walking - Knoydart, Skye & The Small Isles
I wish it was longer, the time went so quickly!

Andrew Baird


Sailing Journeys - The Inner Hebrides
If you love sailing, wildlife and enjoy a bit of wandering ashore then this is for you. As a 'Thames Estuary' man the experience was fabulous.

Nick Ardley


Rated 4.8 out of 5 based on 67 reviews of Sailing

5 star 58

4 star 7

3 star 0

2 star 1

1 star 0

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If you find yourself overwhelmed by the choice, or if you have questions about your fitness or suitability for any of these holidays, please feel free to contact our office on +44 (0)1479 420020 or by email.

2 Trip(s) listed

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46 review(s)

Sailing and Walking - Knoydart, Skye & The Small Isles

Next available trip: 6th May        Duration: 6 night(s)
Location: Inner Hebrides including Skye    
Comfort: Basic
Difficulty: 5
  • Explore the inaccessible rough bounds of Knoydart and some of the most beautiful Scottish Isles aboard a traditional yacht
  • Experience the extraordinary wildlife of Scotland in its most unspoilt wild locations
  • Enjoy some of Scotland's finest walking, accessing rarely trodden routes from the yacht

Price: from £1,295

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15 review(s)

Sailing Journeys - The Inner Hebrides

Next available trip: 29th April        Duration: 6 night(s)
Location: Inner Hebrides including Skye    
Comfort: Basic
Difficulty: 3
  • Explore the finest sailing in Europe, sailing amidst the many beautiful islands which dot the West Highlands coastline
  • Take the wheel of our traditional 75-year old gaff-cutter yacht as you sail from island to island
  • Experience the extraordinary marine wildlife of Scotland in its most unspoilt wild locations

Price: from £850

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Tall Tales – Stories from the Sea

Posted on Nov 28, 2013 by Carol Lang


Sea Kayak guide and storyteller, Carol Lang shares her passion for tall tales – stories from the sea and recommends 6 of her favourite books full of nautical adventure. I love stories in any shape or form and I find it hard to pass by a good book shop without going in for a peek.  […]

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St Kilda – the Atlantic Jewel and World Heritage Site

Posted on Aug 26, 2013 by Phillip Blase


St Kilda – The most westerly point of the UK St Kilda or Hirta lies some 110 miles West of the Scottish mainland, 41 miles West of Uist in the Outer Hebrides and is the UK’s most Westerly territory with the most Westerly point on the island being Canbir at a Lat and long of […]

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