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.

Explore the best of Scotland with Ryder-Walker’s Guided Scotland: Highlands and Islands and the Self-Guided Rob Roy Way. Immerse yourself in the captivating Highlands and Islands trek, featuring our favorite hikes around the charming market town of Callander before traveling to the iconic Isle of Skye. Alternately, embark on the historic Rob Roy Way, tracing the life of the legendary robber-outlaw Rob Roy MacGregor.

You can imagine the old legends of knights and faeries coming to life as you hike through the ancient Scottish woods beneath the summits of the highest peaks in Scotland, the Munros (mountains over 3,000 ft). The Munros are featured in both the Highlands and Islands and the Rob Roy Way itineraries. Meanwhile, the Isle of Skye is a legendary location for good reason – the landscape here is truly austere with jagged peaks, remote villages, and medieval castles all adding to the brooding atmosphere of the landscape. Whether you are starting out your hiking day with a sturdy Scottish breakfast or arriving at a village just in time to catch a sheepdog exhibition, the eternal charm of the Scottish Highlands is sure to inspire you to explore the hidden mysteries of Scotland.

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As a cultural excursion, our tours in Scotland are some of Ryder-Walker’s richest hikes, full of historic locations, local lore, and vibrant living culture. 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. Scottish food is also an unsung hero, with the local pies, pub fare, and farm-to-table restaurants far exceeding the United Kingdom’s dim reputation for cuisine. You might even get a chance to try the infamous haggis, a pudding of spiced sheep’s pluck. Overall, you won’t find more warmth and cheer than in the chilly reaches of the Scottish Highlands and Isle of Skye.

Our Highlands and Islands tour focuses on what we think is the absolute best hiking across Scotland. The section that travels through the Scottish Highlands explores the Trossachs National Park – the same national park that the Rob Roy Way traverses. Here you will hike some of the highest peaks in Scotland and wander through the beech forests that inspired the nature poems of legendary Scottish poet Alexander Campbell. On the Isle of Skye, the trek takes a turn for the more dramatic, as the landscape of the far northern island reveals its true majesty. Notably, the Torridan mountains are a low-lying, and surprisingly dramatic chain of mountains known for their twisted rock formations. Other features of note in Skye are the island’s massive vistas, roaming sheep flocks, and windswept coastline.

The Rob Roy Way follows the life 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 MacGregor 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. We visit the historic home of the MacGregor clan, and the site of his eventual burial. Along the route, the Rob Roy Way explores remote stretches of the Southern Scottish Highlands, across moorland, and along the shores of Loch Tay. 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.

Choose your adventure and discover the beauty, history, and allure of Scotland with Ryder-Walker. Whether you’re drawn to the mystique of the Highlands and Islands trek or the historical charm of the Rob Roy Way journey, both hikes promise an unforgettable exploration of Scotland’s hidden mysteries and lore.

Highlands and Islands

Scotland is a unique country boasting 790 diverse islands, a rugged coastline, thousands of hidden lochs, a distinctive culture, imposing mountains looming stoically against the wilds of the infamous Scottish climate and vast stretches of uncharted trails. During this trek we traverse many miles of awe-inspiring mountains and precipitous glens, summit dramatic peaks and ramble through mossy forests. We visit...

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Guided Tour Date

June 1-11, 2025




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Rob Roy Way

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

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Self-Guided Tour Date





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Hear It From Our Guests

“We did this trek (Rob Roy Way) two years ago and it was amazing. Rogan is a wonderful guide and we had such a good time with him we scheduled his Cotswolds tour. We did that in May and it was another fantastic time. Both are highly recommended.”
Mike P.
“I most enjoyed the days we were on trails or non-vehicle routes and/or trekking over the open moors. We are experienced backpackers, used to camping from a pack, so the luxury of the B&Bs/hotels was great, especially on days we arrived wet. The scenery and variety of habitats was very nice, which impressed me as a birdwatcher and wildlife biologist.”
Robert Luce

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