The Scottish Highlands are one of the world’s premier automobile playgrounds: not only is the magnificent, undulating territory crisscrossed by roads large and small, but it’s almost impossible to end up somewhere you don’t want to be. Getting a bit lost on the single-lane tracks that surround the Isle of Skye’s Cuillin Mountains, for instance, or finding oneself sipping an unplanned afternoon dram in a village pub are the serendipitous lifeblood of a memorable road trip. But some planning does go a long way towards avoiding stress and disappointment, and this nine-stop loop offers overnighting options for all tastes.

Gleneagles

The grande dame of Perthshire will celebrate its centenary in 2024 and remains a destination worth a detour and a fitting place to start (and perhaps end) any trip. There’s world-class golf on three championship courses, multiple standout eateries including a two-Michelin-star restaurant, an almost comically spacious spa, and activities ranging from hillwalking to horse riding.

Inver Restaurant & Rooms

Pause at the majestic Rest and Be Thankful viewpoint, overlooking the top of Loch Fyne, before arriving at Inver, where the convivial, casual atmosphere belies the seriousness of the superb kitchen. Centred on local seafood and game, the ingredients seem to find their natural home in chef Pamela Brunton’s imaginative, balanced dishes. Be sure to book a modern, on-site bothy for the overnight.

Isle of Eriska

This 34-key country-house hotel is set on its own island on the west coast. A place for restorative relaxation, it offers a magnificent spa in the stables and a host of outdoor activities that can (and should) be tailored to the ever-changing weather: the one constant is getting out on the water, whether for sea kayaking, fishing or a guided journey around the nearby isle of Mull and its puffin colonies.

Inverlochy Castle

Consider taking the long way here, backtracking a few kilometres inland to come via the A82 and Glencoe – one of the most beautiful drives in Britain. From there, keeping snow-capped Ben Nevis on your right, the loch-side journey past Fort William brings you to this picture-perfect 19th-century castle, where priority number one is dining at the superlative table overseen by father and son masterchefs Albert and Michael Roux Jr. 

Kinloch Lodge

The two-hour journey to the Isle of Skye is spectacular on roads through Kyle of Lochalsh, but for more novelty (in good weather) try the Mallaig-Armadale ferry. A former family home, Kinloch Lodge is an elegant, well-situated base for exploring the largest and grandest of the Hebridean Isles, from the jagged peaks of the Cuillins to the picturesque villages.

The Torridon

Delightfully positioned, the 18-room hostelry boasts an exceptionally warm welcome. The fine-dining 1887 restaurant received a makeover earlier this year, and highly recommended are the helicopter tours, the hotel’s own gin and a Morgan motorcar day-hire (try the route through Applecross for a jaw-dropping perspective on the west coast’s austere beauty). 

Lundies House

For those taking a longer journey, this coastal bolthole is a cosy destination with a profound sense of place and stillness. Set on property owned by Scotland’s largest landowner – Danish billionaire couple Anders and Anne Povlsen – the serene house is also a stop for those taking in the perimeter of the North on the week-long North Coast 500 route. 

Killiehuntly

The Scandi-inflected farmhouse and self-catering cottages here are also part of the Povlsen portfolio, but their setting, outside Kingussie amid the spectacular Cairngorms National Park, couldn’t be more different. Take a mountain bike ride or try river fishing with a guide on the River Spey, among other activities – and wind down, whatever the choice, with a rejuvenative session in the on-site sauna yurt.

The Fife Arms

From natural beauty to cutting-edge contemporary art, this handsome hotel, on the other side of the Cairngorms from Killiehuntly, is run by art-world titans Hauser & Wirth, who have brought their imposing vision to Braemar – as the more than 14,000 original pieces demonstrate. One of the most stylish hotels in Britain, it’s a fitting finale to the trip and a gentle welcome back to civilisation.