Mountainous views

© Contours Holidays

Rob Roy Way

Rob Roy Way Walking Holidays

Explore Loch Lomond, the Trossachs and the highlands of Perthshire on the Rob Roy Way, a self-guided walking holiday following in the footsteps of the infamous outlaw.

Walk alone or build a walking group from friends and family: all of Contours' walking holidays are self-guided, so it's entirely up to you. Departure times are flexible, and you can add in extra nights at any stop to thoroughly explore a favourite place.

Contours Holidays provide daily luggage transfers, 24/7 emergency support, breakfast each morning, and all the maps and guidebooks you'll need to be your own guide.

We offer two versions of this scenic hiking holiday:

The Full Rob Roy Way

Winding through the region where Rob Roy MacGregor, Scotland's most famous outlaw, used to roam, the Rob Roy Way tours from Drymen to Pitlochry through Trossachs National Park and the highlands of Perthshire. Over passes and through glens, this lovely route follows well-worn footpaths. Complete the trail over five to eight days on one of our self-guided holiday itineraries.

Rob Roy Way Highlights

This shorter walking holiday explores the wildest sections of the Rob Roy Way over 3 to 5 days, clambering woodland paths and following the flanks of lochs as it spans Callander and Aberfeldy.

Rob Roy Way Short Break

This two-to-three-day short break follows the Rob Roy Way between Callander and Killin, with views over Loch Lubnaig and Loch Earn. Enjoy a snippet of the full Great Trail over a long weekend.

Our itineraries are flexible. You can always add extra nights at stops of your choosing to build in some rest days and explore each place in full.

Enquire for more details or book your holiday on our website.

From £695 per adult

Departure days

  • Monday
  • Tuesday
  • Wednesday
  • Thursday
  • Friday
  • Saturday
  • Sunday

March — October

Contact details

Contours Holidays

Unit 11 Via Gellia Mill
Via Gellia Road
Bonsall, Matlock
United Kingdom

Tour information


  • Callander
  • Drymen
  • Pitlochry


5 Days


  • Walking


  • Private


  • Outdoor Activities
  • Walking
  • Walking/Hiking

Tour prices

From £695 Per Adult

Prices are subject to change depending on season

Tour Stops

Contours Holidays

Tour company information

Contours Holidays

Contours Holidays organise self-guided walking, trail running and cycling holidays in Scotland and across the UK. Our self-guided holidays are led by you. We organise all the important details, from daily luggage transfers to nightly accommodation, so you can focus solely on discovering your chosen route at your own pace - with friends, family or out on your own.

Opening times

Our office is open from Monday to Saturday 9:00am to 5:30pm local time, excluding bank holidays.

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