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    Sailing Holidays in Scotland

    Our sailing holidays offer an incredible way to explore Scotland’s wild coastline and remote islands. We offer a limited selection of skippered sailing holidays and due to the world-class nature of the waters we sail and the boats we use, they are popular and often sell out. In addition to joining the crew on board, we also offer yacht charter holidays in Scotland and can tailor to your needs.

    133 review(s)

    Sailing and Walking Tours
    Yacht Charter Holidays
    Skipper and Chef
    Restored Gaff Cutter

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    Set Sail

    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. Depending on the winds, we would usually be sailing in the Hebrides or Malin waters.

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    Let us Take Care of The Details

    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.

    Our Scottish Sailing Holidays

    2 Sailing Trips with 127 Reviews

    Trip Image Trip Flag
    • Enjoy a combined sailing and walking holiday, exploring the Hebrides on a traditional yacht.
    • Experience the extraordinary wildlife of Scotland in its most unspoiled wild locations.
    • Discover some of Scotland's finest walking, accessing rarely-trodden routes from the yacht.
    Next Available Trip:
    3rd June | 29th July
    Inner Hebrides including Skye
    7 Days / 6 Nights
    Blue Grade 5 (Moderate to Challenging) ? What does this mean?
    Click here to learn more about our trip difficulty grading system.
    Carbon Footprint:
    120kg ? What does this mean?
    Click here to find out about our carbon labelling project and what we're doing to be more sustainable.
    Trip Image
    • 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.

    Our holidays reviewed in your own words...

    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.


    Ina Negoita

    Sailing and Walking - Knoydart, Skye & The Small Isles

    Age: 50 - 60
    Country: United Kingdom
    Trip Date: 28/08/2021
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    Worthwhile experience, don't miss it. I may consider it to do it again


    Trina Gavan

    Sailing and Walking - Knoydart, Skye & The Small Isles

    Age: 60 - 70
    Country: United Kingdom
    Trip Date: 28/08/2021
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    We were so fortunate to experience incredibly perfect weather for sailing and walking, which of course contributed hugely to our enjoyment and appreciation of some of Scotland's wild and remote places. I am also convinced that we would not have had such an amazing time had it not been for the organisation, knowledge and skill of all the Wilderness Scotland staff, who work so hard in the background to ensure their clients have the best ever holiday. Thank you!


    Hugh Pringle

    Sailing and Walking - Knoydart, Skye & The Small Isles

    Age: 70 - 80
    Country: United Kingdom
    Trip Date: 28/08/2021
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    It was a very memorable trip which I would really want to repeat, or at least something similar.

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    Popular Sailing Holidays in Scotland

    TripNext DeparturePriceDuration 
    Sailing and Walking – Knoydart, Skye & The Small Isles 04/06/2022 £1,995 6 Nights Trip Details
    Sailing Journeys – The Inner Hebrides 30/07/2022 £1,100 6 Nights Trip Details

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