Scotland by Trail: An Active Journey to the Highlands

Following an overnight flight, arrive in Glasgow and transfer to your historic hotel in the city center. The rest of the day is yours to get acquainted with this dynamic city, known for its unique architecture. Consider a short walk to the Glasgow School of Arts, an iconic building designed by Scottish architect Charles Rennie Mackintosh, or take a stroll through pedestrian streets of the old town. Meet your trip leader and fellow travelers this evening for a welcome briefing and dinner. (D)

After breakfast, head for Loch Lomond and the Trossachs National Park, a rippling landscape of hills and lakes that became Scotland’s first national park in 2002. From the tiny village of Balmaha, set out on your first hike, following a section of the West Highland Way along the oak-lined shores of Loch Lomond. Admire forest views from the lakeshore, or continue hiking up a rugged slope towards a viewpoint on Conic Hill, where sweeping views of the park’s waterways and islands await. Stop for lunch at a local restaurant before driving east to Loch Awe. Take a guided tour of the intriguing St. Conan’s Kirk, where a mash-up of architectural styles offers up plenty of surprises. Late this afternoon, arrive in the seaside town of Oban, the gateway to the Inner Hebrides, and check in to your hotel. Your evening is at leisure. (B,L)

Hiking: 3-4 miles over some steep steps and a short rocky scramble; 1,100 feet of elevation gain.

Start the day with a short ferry ride to the rugged island of Kerrera, just off the coast of Oban. This morning’s trail circles the island’s southern half, crossing the rolling hills of the interior and then following the coast. Take in views of the surrounding islands if the weather is clear, and hike amid meadows and hillsides dotted with sheep—they far outnumber the residents on the island. On a rocky promontory overlooking the sea, encounter the well-preserved tower of Gylen Castle, built as a stronghold of the MacDougall clan in 1582 and burned 65 years later.Take a ferry back to the mainland for lunch, then join your trip leader for an afternoon walk through the charming Oban, which means "little bay" in Gaelic. Wander past local shops and gain insight into Oban’s seafaring culture, then opt to continue up to McCaig’s Tower, a local landmark on Battery Hill with scenic views of the bay. With a free evening, opt to try a local seafood restaurant—Oban is Scotland’s seafood capital—or grab dinner with fellow travelers at a local pub. (B,L)

Hiking: 6-7 miles on an undulating trail with grassy paths and some steep ascents over rocky terrain; 700-800 feet of elevation gain. Those who prefer may shorten this hike by returning from Gylen Castle to town independently.

Walking: 1-2 miles on city streets; optional ascent to Battery Hill with elevation gain of 160 feet.

Awaken for an early breakfast before driving along the shores of Loch Linnhe to hike a section of the fabled West Highland Way, which stretches nearly a hundred miles through the Scottish Highlands. Set off on a trail that traverses the Glencoe Valley, ending at the foot of majestic Aonach Eagach, a steep, exposed ridge known for the zigzagging pass called Devil's Staircase. Continue by coach to Glencoe, a spectacular valley where the notorious massacre of the MacDonald clan by government soldiers took place in 1692. After lunch in the village of Glencoe, hike a loop trail through forests to a lake ringed by mountains. Keep an eye out for interesting birds and other wildlife as you walk. Alternatively, stay in the village to visit its museum. Travel on to Fort Augustus, at the tip of Loch Ness, and settle into your hotel before an evening at leisure. (B,L)

Hiking: 4 miles mostly on gravel with uneven terrain, 300 feet of elevation gain

Walking: 2-mile loop trail on easy paths, 300 feet of elevation gain.

Spend a full day on the magical Isle of Skye, exploring its craggy mountains, peat moors, and wild geological formations. Begin with a visit to Dunvegan Castle, founded in the 13th century by the MacLeod clan, and stroll through its award-winning formal gardens. Continue to the picturesque fishing village of Portree where you’ll have free time for lunch on the waterfront. Later, travel north to the Trotternish Peninsula, home to some of Skye’s most unusual rock formations. The afternoon’s hike winds through an otherworldly landscape of soaring cliffs and undulating green slopes to a cluster of narrow pinnacles—the tallest of which is known as the Old Man of Storr. Take in awe-inspiring views out over the Sound of Raasay from these iconic rocks. Return to Fort Augustus late this afternoon and gather for dinner together. (B,D)

Walking: 1-2 miles around the castle and gardens, mostly flat.

Hiking (afternoon): 3 miles over hilly trails with some rocky terrain; 1,000 feet of elevation gain.

Drive north along the shores of Loch Ness this morning, stopping in the town of Fort Augustus for a short walk along the Caledonian Canal. Continue to Urquhart Castle and hear about its dramatic history, then enjoy time to explore the lakeside castle ruins on your own. Turn east toward Cairngorms National Park, pausing at historic Culloden Moor for a visit to the battlefield where the Jacobite Rising came to an end in 1746. Go on a peaceful hike through the ancient pines of Rothiemurchus forest and skirt the shores of Loch an Eilein and Loch Gamhna, catching sight of a crumbled 13th-century castle on a lake island. Journey on to the lively town of Pitlochry and enjoy a evening at leisure. (B,L)

Walking: 1-2 miles along a flat lakeshore path. 

Hiking (afternoon): 4-5 miles over hilly and forested terrain, 500 feet of elevation gain.

Take a walk through time with a local guide, discovering the sites of Pitlochry and the surrounding countryside. Following path, track, and field, ramble from the 120-foot-high Black Spout waterfall to the ruins of Caisteal Dubh, or the Black Castle. Continue to the village of Moulin, home to an old inn and brewery, and encounter a prehistoric standing stone in a nearby field. Reach the banks of Loch Faskally and cross the Pitlochry dam and fish ladder. Sit down to a well deserved lunch before a guided visit to the Blair Atholl Distillery. Follow a whisky expert through the process of producing whisky from local water sources, and end the tour with a tasting. The remainder of the day and evening are yours to explore Pitlochry on your own. (B,L)

Hiking: 5-6 miles with a mix of hills, valley and forest trails, occasionally rocky and uneven; 700 feet of elevation gain.

Journey from Pitlochry to Edinburgh, where you’re joined by a local expert for a guided walking tour of the city center. Stroll the Royal Mile, tracing Scotland’s turbulent history and the evolution of Edinburgh. Stop for lunch on your own at one of the many pubs and eateries in Old Town or along Princes Street. During a free afternoon, discover this enchanting capital city as you wish, perhaps on a tour of Edinburgh Castle or a hike to the top of Arthur’s Seat, an ancient volcano overlooking Edinburgh. Meet up with the group to toast your hike through Scotland at a festive farewell dinner at one of the city’s great restaurants. (B,D)

Walking: 2-3 hour city tour, hilly city streets; 200-300 feet of elevation gain.

After breakfast, transfer to the airport for your flight home. (B)