The Scottish Highlands remain a mysterious frontier even after thousands of years of human settlement. Somehow the sweeping moors, deep forests, mountain valleys, and deep lochs remain as interminable and intriguing as they were when the Scottish so heartily rebuked both the Romans and the English.

In Scotland, Ryder-Walker offers the Rob Roy Way as our trek of choice, a historic route that follows the life of legendary robber-outlaw Rob Roy Macgregor. The Rob Roy story is often likened to that of a real-life Robin Hood. A tale of clan politics and resisting the changing world from the insular world of the remote highlands, Rob Roy himself gained notoriety as a cattle thief and would end his life as a hero to all of Scotland. Along the Rob Roy Way, we visit locations where Rob Roy did battle with Spanish pirates, hid and escaped from the law, the historic home of the Macgregor clan, and the site of his eventual burial. 

Beyond following the life of Rob Roy, the route of The Rob Roy Way explores remote stretches of the Southern Scottish Highlands, crossing massive moors, enjoying a sheep show in the village of Aberfeldy, walking along the shores of Loch Tay, and a night in a hotel at the site of an old Roman war camp in Callander. As we explore these wonders and more, it’s hard not to fall in love with the Scottish sense of life. At night cheery traditional Scottish music fills the pubs with the sounds of fiddles, guitars, pipes, flutes and drums. Meals are prepared with heart and expertise. All of the accommodations have the touches of love that only those truly dedicated to the craft of hospitality can create. Overall, you won’t find more warmth and cheer than in the chilly reaches of the Scottish Highlands

The Rob Roy Way is the perfect hike for someone who is looking for an adventure without any grueling challenge. While the Scottish wilderness is impressive and often austere, the hiking maintains a certain levity, and the Scottish Munros are never so huge that the hiking becomes truly difficult for any reason other than distance. As a cultural excursion, the Rob Roy Way may be one of Ryder-Walker’s richest hikes; full of historic locations, local lore, and accompanied the entire way by the legend of Rob Roy himself.

Guided Tours: Scotland

loch katrine Scotland

Walk in the footsteps of one of Scotland’s most legendary outdoorsmen and greatest heroes – Rob Roy MacGregor. Through green meadows, along the coasts of sapphire lochs and across the feet of wind-swept Munros (peaks over 3,000 feet), we walk as he did during this nine-day hiking tour through a beautiful region of the Scottish Highlands called the Trossachs. Who was Rob Roy? Rob Roy MacGregor was ...

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Self-Guided Tour Date

March - October

Guided Tour Date

May 19-27, 2023




Trip Ratings Explained

*All prices are per person based on double occupancy and subject to change