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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.

    126 review(s)

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

    We are open for bookings and are running holidays and trips

    We remain true to our values and we're reopening in a considered way, that respects each of you as individual travellers, while in equal measure respecting the communities that we visit.

    Travel Planning and Advice

    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.

    View All Sailing Holidays

    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 120 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:
    28th August | 7th May
    Inner Hebrides including Skye
    7 Days / 6 Nights
    Blue Grade 5
    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.
    Next Available Trip:
    30th July
    Inner Hebrides including Skye
    7 Days / 6 Nights
    Green Grade 3

    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.


    Penny Hogg

    Sailing Journeys - The Inner Hebrides

    Age: 60 - 70
    Country: England
    Trip Date: 27/07/2019
    Trips Taken: 3

    The Bottom Line

    The Bottom Line

    All things combined to make it a fantastic once in a lifetime experience. TEAM WILDERNESS RESPONSE: "Once in a lifetime" is high praise indeed and we're really glad you had such a fantastic time aboard Eda.


    Laura Fitch

    Sailing and Walking - Knoydart, Skye & The Small Isles

    Age: 60 - 70
    Trip Date: 20/07/2019
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    on a scale of 1-5 it was actually a 10! One of the best vacations ever!


    Carrie West

    Sailing and Walking - Knoydart, Skye & The Small Isles

    Age: 70 - 80
    Country: United States
    Trip Date: 20/07/2019
    Trips Taken: 1

    The Bottom Line

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    Popular Sailing Holidays in Scotland

    Trip Next Departure Price Duration  
    Sailing and Walking – Knoydart, Skye & The Small Isles 28/08/2021 £1,850 6 Nights Trip Details
    Sailing Journeys – The Inner Hebrides 14/08/2021 £1,020 6 Nights Trip Details

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