Road Cycling Holidays in Scotland : Wilderness Scotland
UK: +44 (0)1479 420 020
US: 1-866-740-3890
National Geographic - Best Adventure Travel Companies
Pinterest Facebook Twitter
Book on Black Week and get a free Haglofs Lim Barrier Pro Jacket worth £200

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

Superb scenery, quiet roads and great hospitality are the hallmarks of a road cycling trip with us.

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 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 ride 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
It has long been a dream of mine to visit the Western Isles, I have been really looking forward to it for weeks and even then it still surpassed all expectation. From the professionalism and support of your team, to the friendliness of the people we met on the islands, my fabulous holiday companions, the spectacular beauty of the Islands, my sore bum..... all make this holiday an experience that I wont forget.

Pamela Duncan


Road Cycling - Outer Hebrides
A very enjoyable way of seeing some wonderful countryside and getting some exercise, while being thoroughly looked after; but inevitably quite expensive, and for that reason alone I would recommend this kind of trip to friends selectively.

Lucy Wood


Road Cycling - Island Explorer
The trip exceeded all expectations and we are already browsing the Wilderness Scotland website to choose which trip to do next year (we would have booked for later this year but many of the trips are already fully booked - testamount to their popularity!)

Lynn Owens


Rated 4.9 out of 5 based on 72 reviews of Road Cycling

5 star 66

4 star 6

3 star 0

2 star 0

1 star 0

Read All Trip Reviews

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.

6 Trip(s) listed

Sort Your Selection:

42 review(s)

Road Cycling - Outer Hebrides

Next available trip: 30th 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 £1,495

View Trip Details
18 review(s)

Road Cycling - The Grand Tour

Next available trip: 4th June        Duration: 6 night(s)
Location: Multi-Location    
Comfort: Classic
Difficulty: 5
  • Soak up the diverse beauty and culture of Scotland on a journey from the capital of the Highlands to the capital of the Lowlands
  • Explore the ancient town of St Andrews, visit Edinburgh castle and freewheel down the famous Royal mile
  • Ride through the Cairngorms National Park, pass the Queens residence at Balmoral Castle and enjoy a stop at the whisky distillery

Price: from £1,395

View Trip Details

Road Cycling - Highland Coast to Coast

Next available trip: 28th 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 £1,395

View Trip Details
8 review(s)

Road Cycling - Island Explorer

Next available trip: 18th June        Duration: 5 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 £1,395

View Trip Details

Road Cycling - Skye and the Inner Hebrides

Next available trip: 21st 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 £1,495

View Trip Details
4 review(s)

Road Cycling - The Mountain Passes

Next available trip: 7th May        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 £1,295

View Trip Details
Talking Lycra: The Pros and Cons of Cycling Bib Shorts

Posted on Sep 16, 2015 by Paul Easto

cycle bibs Scotland

I feel as if I should start this gear review with a confession. For over 20 years I was of the “not to be persuaded mindset” that the only form of biking worth doing was mountain biking. Consequently bib shorts were somewhat of a novelty. In fact, up until a couple of years ago when […]

Continue Reading
Our new Adventures for 2015 are now live!

Posted on Jan 17, 2015 by Rupert Shanks

Our new Adventures for 2015 are now live!

  The latest, greatest and brand new wild Scottish adventures we’re launching for 2015. Here at Wilderness HQ we are often dreaming about places we want to go, activities we want to try there and the best in local eateries to feed us when we re there. So it is no great hardship to create […]

Continue Reading

Read all Road Cycling Articles »