Mountainous views
Rob Roy Way © Contours Holidays

Rob Roy Way Walking Holidays

From £590 per adult

Departure days

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March — October

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 Country Short Break

This three-day short break follows a circular route out of Callander through the hills and glens at the heart of Rob Roy country. Follow the shores of two lochs and tour historic sites 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.

Contact details

Contours Holidays
Unit 11 Via Gellia Mill
Via Gellia Road
Bonsall, Matlock
United Kingdom
Callander Drymen Pitlochry
Outdoor Activities Walking Walking/Hiking

Tour prices


  • £590 Per Adult


Tour company information

Contours Holidays

Contours Holidays organise self-guided walking and trail running holidays in Scotland and across the UK. Our self-guided walking 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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