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National Geographic - Best Adventure Travel Companies

Road Cycling Holidays

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

Quiet roads and great hospitality; the hallmarks of a Wilderness Scotland road cycling holiday.

Our road cycling holidays in Scotland feature spectacular landscapes and some of the most culturally interesting places you will find in Europe.

Our holidays range from an easy cruise through the Outer Hebrides islands to a challenging week of riding the highest mountain roads in the UK. Our on-the-road approach balances great guiding and insights when you would like it, alongside the freedom to explore at your own pace.

Our trips are led by a qualified and experienced guide but you also receive detailed route notes for each day’s ride. You can choose to cycle Scotland with your guide or simply follow the route notes meeting up with the group at designated stops along the way.

Throughout the day, our support vehicle will always be close to hand to provide drinks, snacks and a friendly ride should you need it. It also transfers your luggage between hotels, gearing you up for a lightweight and care-free ride.

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.

Road Cycling - Outer Hebrides
A great trip to a beautiful part of Scotland that many will miss due to its extreme location but Wilderness Scotland have made the trip accessible & easy for most

Charles Robertson


Road Cycling - Outer Hebrides
Beautiful and memorable

Jane Tapp


Road Cycling - The Grand Tour
I would recommend Wilderness Scotland for anyone considering a cycling trip in Scotland. As much as I love Scotland, I cannot recommend it as a first choice destination for a European cycling trip given the unpredictability of the weather. We got very lucky!

Ron Torok


Rated 4.90 out of 5 based on 181 reviews of Road Cycling

5 star 166

4 star 12

3 star 3

2 star 0

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.

7 Trip(s) listed

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85 review(s)

Road Cycling - Outer Hebrides

Next available trip: 28th April        Duration: 6 night(s)
Location: Outer Hebrides and St Kilda    
Comfort: Classic
Difficulty: 4
  • Cycle tour from Barra to Lewis through nine amazing islands of the Outer Hebrides.
  • Admire the outstanding landscapes of white sand beaches and towering shapely peaks.
  • Enjoy the fascinating history, rich culture and warm hospitality of the islands.

Price: from £1,695

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10 review(s)

Road Cycling - The Five Countries

Next available trip: 14th May        Duration: 11 night(s)
Location: Multi-Location    
Comfort: Classic
Difficulty: 6
  • Ride through the fantastic 5 countries of Great Britain & Ireland
  • Experience the culture of 5 different nations journeying through the best of scenery from wild mountains, to scenic coast, castles and charming villages
  • Explore the roads made famous by the Tour de France, Tour of Britain & Tour of Ireland

Price: from £2,895

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22 review(s)

Road Cycling - Island Explorer

Next available trip: 12th May        Duration: 6 night(s)
Location: Multi-Location    
Comfort: Classic
Difficulty: 3
  • Island hop across 3 of Scotland's best islands - Arran, Islay and Jura
  • Enjoy world class whisky and wildlife on the beautiful Island of Islay
  • Visit the third largest whirlpool in the world en route to the Kingdom of Argyll

Price: from £1,795

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15 review(s)

Road Cycling - Coast to Coast

Next available trip: 26th May        Duration: 6 night(s)
Location: Multi-Location    
Comfort: Classic
Difficulty: 7
  • Ride right across Highland Scotland from the east to the west coast
  • Quiet roads, testing climbs and superb descents through the UK's most spectacular landscapes
  • Visit the beautiful Cairngorms National Park, atmospheric Loch Ness and the mighty mountains of Torridon

Price: from £1,595

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32 review(s)

Road Cycling - The Grand Tour

Next available trip: 5th May        Duration: 6 night(s)
Location: Multi-Location    
Comfort: Classic
Difficulty: 5
  • A classic road cycling tour from the heart of the Highlands to Scotland's Capital.
  • An amazing week of trip highlights showcasing the best of Scotland's natural and cultural heritage and warm hospitality.
  • Full guiding, vehicle and logistical support leaving you to relax and enjoy the riding.

Price: from £1,695

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13 review(s)

Road Cycling - Skye and the Inner Hebrides

Next available trip: 19th May        Duration: 6 night(s)
Location: Inner Hebrides including Skye    
Comfort: Classic
Difficulty: 3
  • 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.

Price: from £1,695

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4 review(s)

Road Cycling - The Mountain Passes

Next available trip: 18th August        Duration: 6 night(s)
Location: Multi-Location    
Comfort: Classic
Difficulty: 8
  • Soak up the views across to Skye and the Outer Hebrides while you journey over the UK's highest road climb - the 'Bealach na Ba'
  • Enjoy spectacular scenery, challenging climbs and exciting descents through 5 different mountain ranges
  • Visit Scotland's most famous landmarks, indulge in the locally sourced food and relax in comfortable inns and hotel

Price: from £1,495

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Solo Travel: Making New Friends on the Island Explorer

Posted on Sep 08, 2017 by Russell Murray


Solo travel can be a bit daunting, especially if it’s something you’ve never done before but I think this wonderful quote from WB Yeats sums up the reasons you should give it a go: “There are no strangers here; only friends you haven’t met yet.” When I joined our Island Explorer road cycling trip at […]

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Scotland’s Stonehenge: The Standing Stones of Callanish

Posted on Jun 21, 2017 by Neil Irvine

Today marks the longest day of the year - The Summer Solstice. The Standing Stones of Callanish are an incredible place to visit and celebrate the extra daylight.

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