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Selected Trips

    Self Guided Cycling

    New for 2021, join one of our self guided cycling trips in the Cairngorms, the Scottish Highlands and beyond.
    Based on favourite routes, enjoy the flexibility to travel at your own pace with your own private group.

    17 reviews

    Travel Planning & Advice

    Our assurance that we continue to deliver responsible and financially protected adventure holidays.

    Book With Confidence

    Book your self guided cycling holiday with Europe's No.1 Adventure Travel Company

    Each of our self guided cycling holidays have been designed by cycling experts to include the very best of each region. Experience the alluring magic of the Scottish Highlands and Islands with each mile you pedal.

    Self guided is the perfect solution for those who want to explore the wilds of Scotland at your own pace, and value a bit more flexibility. Cycling at your own pace, you’ll enjoy the freedom to speed up or slow down according to your preferences, venture off to any of the many fascinating stops along the way or stop to get the perfect photo, without feeling like you’re on someone else’s schedule.

    Quality Assured

    To ensure a high level of comfort and friendly service, we hand-pick your accommodation. Generally 3 to 4 star as standard, your accommodations are chosen for their high level of cosiness and comfort, friendly service, and ideal locations.

    Enjoy daily cycling routes chosen by locals and trip designers to share the very best of the Scottish wilds with you. Looped routes and luggage transfers mean that you’ll only carry with you what you need for the day.

    Self guided tours are ideal for couples or groups of friends who prefer a private tour during which you can travel at your own pace.

    You can expect to enjoy cycling in Scotland by exploring a variety of exhilarating routes, roads and country lanes during an epic adventure during which you’ll explore our country’s most spectacular landscapes, diverse flora and fauna, as well as rich culture and history.

    Guided vs Self Guided

    Guided Read More

    These trips are led by two qualified and experienced Wilderness guides. Switching roles each day, one of these guides will cycle on the road with you each day giving guidance and imparting their local knowledge of the landscape, flora and fauna. While the other acts as an all-round trip wizard driving the support vehicle, shuttling luggage, preparing gourmet coffee stops and lunches, acting as mechanic, taking care of essential tour arrangements and a whole lot more besides.

    For further insight and full details please check out guided cycling tours.

    Self Guided Plus+ Read More

    Our Self Guided Plus+ trips are not guided but provide a highly personalised level of support you won’t find on regular self-guided bike tours. A dedicated member of the Wilderness Team will be on hand throughout the trip, preforming the equivalent role of the “soigneur” a key member of every pro cycling team. Essentially they will take care of everything on the trip, except for the riding. Throughout your adventure, they will be on hand to drive the support vehicle, transferring your luggage, provide snacks and drinks throughout the day, shuttle riders where required, offer navigational advice, first aid and take care of cleaning and servicing bikes at the end of the day. On each trip, you can choose to bring your own bike or hire (for an additional charge) a high-end Trek bike.

    Using the route files and Garmin GPS head units provided, you can choose to ride at your own pace stopping for coffee and lunches along the way at locations recommended by your Soigneur. As with our guided trips, you will stay at hand-picked accommodation pre-booked by us and, in the evenings, you can choose to eat from a selection of recommended restaurants.

    Self Guided Read More

    This is our simplest type of cycling trip which is neither guided nor supported. On each trip you can choose to bring your own bike,  or hire (for an additional charge) a high-end Trek bike, accompanied by a Garmin Edge 1030 GPS with route notes fully loaded. In addition, you will also be provided a digital copy of each day’s route, along with recommendations for places of interests, cafes and local lunch spots.

    All of your accommodation will be pre-booked by us using the same care and attention we apply to all of our other cycling trips. Each day your luggage will be transferred from place to place, leaving you free to ride with only the items you need. In the event of any problems on the road, we offer an on-call support service to ensure you receive the necessary assistance wherever you might be.

    Compare These Trips Read More
    What’s Included on the Trip
    Self Guided+
    Self Guided
    Qualified Expert Guides
    Guidance and Local Insights
    Support Vehicle
    Most Meals
    Gourmet Picnic Lunches
    Ride Snacks & Drinks
    Baggage Transfer
    Bike Maintenance & Care
    Premium Bike RentalOn RequestOn RequestOn Request
    Expert Bike FitOn RequestOn RequestOn Request
    Garmin GPS & Route Notes
    On Trip Support24/7 Phone
    First Aid Cover

    Our Self Guided Cycling Holidays

    4 Self Guided Cycling Trips with 17 Reviews

    • Island-hopping through Mull, Iona and Skye on this easy-graded road cycling adventure
    • Quiet country roads, cultural encounters, great landscapes and stunning island scenery
    • Cycle to the Isle of Iona and explore its ancient abbey
    • Enjoy the journey as your soigneur / support guide takes care of all the details
    • Experience the freedom of just turning the wheels as your luggage is transferred each day
    • Relax in the knowledge that you are supported every mile of the adventure
    • Ride Scotland's newest long-distance cycle route from the Mull of Kintyre to the Highland Capital of Inverness
    • Experience some of Europe's most spectacular scenery by bike, through the majestic mountains and coastline of the West Highlands
    • Ride off the beaten track and explore the rich heritage of Scotland in places such as the remarkable Kilmartin Glen
    • Ride the entire length of the Outer Hebrides, crossing 10 islands by bike and boat
    • Experience some of Europe's most unspoiled and beautiful landscapes with breathtaking coastal scenery
    • Enjoy the Gaelic culture, history and hospitality of these amazing islands
    Trip Flag
    • Enjoy full vehicle and mechanical support from a qualified guide, while enjoying the freedom to cycle at your own pace
    • Ride along beautiful isolated roads surrounded by some of the most spectacular mountain and coastal scenery in the UK
    • Pit yourself against the famous Bealach na Ba - voted as the best day cycle in the UK
    • Enjoy the journey as your soigneur / support guide takes care of all the details
    • Experience the freedom of just turning the wheels as your luggage is transferred each day
    • Stay in handpicked warm and welcoming highland accommodation

    Guided Road Cycling Trips

    Looking for something different? Discover our range of guided cycling trips.

    View All Guided Trips

    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.


    Kirstie Birmingham

    Self Guided+ Cycling - Skye & the Inner Hebrides

    Age: 30 - 40
    Country: United States
    Trip Date: 27/09/2022
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    An amazing experience cycling the Inner Hebrides! Finlay, our bike hire and guide, went above and beyond to ensure we were well equipped and had a great adventure!


    Thomas Birmingham

    Self Guided+ Cycling - Skye & the Inner Hebrides

    Age: 50 - 60
    Trip Date: 27/09/2022
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    Excellent time! We'd do it again in a heartbeat.


    Osnat Frumerman

    Self Guided+ Cycling - The Caledonia Way

    Age: 50 - 60
    Trip Date: 05/08/2022
    Trips Taken: 1

    The Bottom Line

    The Bottom Line

    Attention to small details is the key to the success of the trip! and It was there

    Speak to an Expert

    Stevie Christie

    As an avid adventurer, Stevie has life-long experience in Scotland’s outdoors. He’s Co-Owner and Head of Adventure with Wilderness and been with us for over 15 years in a variety of roles, with innovative trip design being both a passion and a speciality. In his spare time, Stevie runs the Edinburgh Mountain Film Festival, bringing the world’s most inspiring adventure filmmakers and athletes to an audience of over 1,500 each year.

    Ask Stevie a Question

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