Castles, Viking Heritage, and Prehistoric Monuments with Skye McDonald


Experience Scotland’s exquisitely remote locations on a journey filled with dramatic coastal scenery, Neolithic standing-stone monuments, echoes of Viking settlers…and elegant malt whiskies. We steep in a heady mix of prehistoric sites and rich Viking influence on the Orkney Islands, whose inhabitants identify with their Scandinavian heritage as much as their Scottish citizenship. It’s a fascinating cultural blend.

We hike right into the standing stone circle at the Ring of Brodgar, a ceremonial circle older than Egypt’s pyramids, and discover Neolithic Skara Brae, an astonishingly intact ancient settlement. In Scotland’s far north, we’ll be off the tourist trail, on moorland and coastal hikes across rugged landscapes dotted with fishing villages. We visit a 16th-century castle, view intricately carved Pictish stones, and learn about the infamous Clearances that led many Highlanders to emigrate to the U.S. and Canada.

Itinerary at a Glance

Days 1-2
Falconry / Ancient Heritage / Local Music

We’ll hike along some of Britain’s most spectacular sea cliffs, visit an inventive chapel built during WWII by Italian POWs, and you can even try your hand at falconry. Our explorations include two iconic UNESCO sites: the Ring of Brodgar, a ceremonial circle where we walk among standing stones erected before the Egyptian pyramids, and the ancient village of Skara Brae, an active archaeologic site that gives us an extraordinary window into Neolithic life. Head out to a pub for live music and an evening with the locals.

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Days 3-4
Vikings / Boat Building

Our morning hike brings us to the famous Old Man of Hoy seastacks and we walk above Rackwick Bay’s blushing pink-and-cream beach. In the afternoon we’ll meet a traditional Orkadian boat builder to learn about the magnificent Viking longships and hear tales of the area’s Viking heritage.

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Days 5-7
Mainland Hikes / Highland History / Whisky Tasting / Fairytale Castle

After a ferry ride to the mainland we’ll enjoy hikes through breathtaking scenery, from rolling fields and heathered moorlands to pine forests and dramatic gorges. Coastal views give us an excellent opportunity to watch for sea birds, seals, and dolphins. We’ll stop in to visit Glenmorangie Distillery—where we learn about whisky creation at a special tutored tasting of several single-malt expressions—and the Emigrants Statue, which commemorates the people who were removed from their homes during the Highland Clearances in the 18th and 19th centuries. Relax at a fairytale-style castle with a remarkable Victorian-era museum.

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Days 8-9
Pictish History / Outlander-Style Visit

Our hike brings us to a magnificent 8th-century Pictish monument that is one of Scotland’s most important artistic treasures, and opens the door to understanding the mysterious people who lived here during the late Iron Age and early medieval period. A village visit immerses us in a lively arts scene and traditional architecture. We’ll even share some time with a real-life earl whose family members have been at the epicenter of Highland and Scottish politics and adventure for hundreds of years.

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Explore two iconic prehistoric sites: the Ring of Brodgar with its magnificent standing stones; and Skara Brae, an active archaeological site
Hike along stunning coastal and island trails to the extremities of these rugged lands
Meet with a local Orkadian boat builder who shares his knowledge of Viking longships
Visit sites that are a stark reminders of the infamous Highlands Clearances
Sample fine single-malt whiskies of the northern Highlands in a private tutored tasting
Learn about the mysterious Picts who lived here during the Iron Age and left beautiful, enigmatic carvings


Length: 9 days
Cost From: $6095  
Arrive: Kirkwall, Scotland
Depart: Inverness, Scotland
Lodging: 8 nights hotels
Meals: All meals included (B=Breakfast, L=Lunch, D=Dinner)
Activity: Hiking / Trekking
Trip Level:

5 hiking days on moderate to steep trails, 2-4 hours a day, van support (for luggage or if you wish to skip a day’s hike)