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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 trips, 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 private charters in Scotland which can be tailored to your request.

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

      Travel Planning & Advice

      Book With Confidence

      Set Sail

      Discover the joy of sailing in Scotland as you explore the rugged coastline and stunning westerly isles by yacht. We sail and explore by day and stay on the boat by night, often moored in remote wilderness anchorages.

      These trips combine sailing and gentle walking as a great way to explore Scotland. Although we have outline itineraries, these are flexible, allowing us to make the most of the weather and the wind. During your adventure, you may choose to become fully involved with life on board or simply take the opportunity to relax as the captivating coastline unfurls beyond the bow. On trips that include walking on the islands, you will be joined by a professional hiking guide.

      We also arrange private charters, allowing you to craft the perfect voyage. Due to demand, these trips must be arranged 12 – 18 months in advance. Visit our tailor-made page for more details here.

      View All Sailing Holidays

      Our Scottish Sailing Holidays

      3 Sailing Trips with 139 Reviews

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      Available Trip Dates
        Location
          Grading
            Duration

              Sailing Journeys - The Inner Hebrides

              46 review(s)
              • Journey ashore to explore pristine beaches, ancient ruins and lofty mountain peaks
              • Hike the beautiful shores of remote islands, spotting coastal plants, birds and wildlife
              • Enjoy time spent on the stunning traditional gaff-cutter, gliding up the captivating coastline
              Next Available Trip:
              1st June | 20th July
              Region:
              Inner Hebrides including Skye
              Duration:
              7 Days / 6 Nights
              Grading:
              Green Grade 3 (Easy - Moderate) ? 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.
              Download Itinerary View Trip Details

              West Coast of the UK

              • Experience sailing under the stars in the twinkling darkness of the Irish Sea.
              • Hike the beautiful shores of uninhabited and remote islands, spotting coastal plants, birds and wildlife.
              • Wild swim from the deck of Eda, exploring turquoise depths and hidden coves.
              • Immerse yourself with life on board, actively participating in the sailing adventure.
              Next Available Trip:
              27th April | 14th September
              Region:
              Multi-Location
              Duration:
              10 Days / 9 Nights
              Grading:
              Blue Grade 4 (Moderate to Challenging) ? What does this mean?
              Click here to learn more about our trip difficulty grading system.
              Carbon Footprint:
              144kg ? What does this mean?
              Click here to find out about our carbon labelling project and what we're doing to be more sustainable.
              Download Itinerary View Trip Details
              X
              Sailing
              West Coast of the UK

              This trip is operated by our England team. Clicking on the links below will redirect you to the Wilderness England website.

              Sailing and Walking - Knoydart, Skye & The Small Isles

              93 review(s)
              Trip Flag
              • Enjoy the perfect blend of sailing and walking as you explore the Inner Hebrides
              • Discover Scotland's wonderful wildlife in the most pristine and remote locations
              • Explore Scotland from the bow of a boat on the beautiful gaff-cutter Eda Frandsen
              Next Available Trip:
              29th July | 25th May
              Region:
              Inner Hebrides including Skye
              Duration:
              7 Days / 6 Nights
              Grading:
              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.
              Download Itinerary View Trip Details

              Our holidays reviewed in your own words...

              134
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              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.

              RL

              Renee Lynch

              Sailing Journeys - The Inner Hebrides

              Age: 50 - 60
              Country: Netherlands
              Trip Date: 30/07/2022
              Trips Taken: 1

              The Bottom Line

              The Bottom Line

              The trip exceeded our expectations. We had some very nice sailing journeys and the Eda Frandsen crew did an outstanding job. Thank you Mungo, Stella and Mo, you are the best.

              Show More
              CM

              Claire Mackenzie

              Sailing Journeys - The Inner Hebrides

              Age: 50 - 60
              Country: Scotland
              Trip Date: 30/07/2022
              Trips Taken: 1

              The Bottom Line

              The Bottom Line

              Very happy to recommend

              Show More
              MB

              Maggie Bartlett

              Sailing Journeys - The Inner Hebrides

              Age: 60 - 70
              Country: United Kingdom
              Trip Date: 30/07/2022
              Trips Taken: 7

              The Bottom Line

              The Bottom Line

              I have been on several trips with Wilderness Scotland and have always been impressed with the attention to detail and the commitment of everyone involved to ensure that things go well. I will have no hesitation in booking more trips in the future.

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              Popular Sailing Holidays in Scotland

              TripNext DeparturePriceDuration 
              Sailing and Walking – Knoydart, Skye and The Small Isles 03/06/2023 £2,295 6 Nights Trip Details
              Sailing Journeys – The Inner Hebrides 10/06/2023 £1,320 6 Nights Trip Details

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