Edinbrrrr…! Great Scot! Finding The historic Haunts (And Hot Men In Kilts) In Scotland’s Capital City

It's Dreich—wet, dismal, dreary—and cauld, as they might say here. Gale-force winds threaten to send me hurtling off the Scott Monument. A tower of Gothic spires and protruding gargoyles representing characters from Sir Walter Scott’s novels, it resembles a sandstone spaceship poised for takeoff.

I hang on for dear life; I’m staying right here.

Edinburgh, you quickly learn, has earned its reputation for stroppy weather. Often, the city is shrouded in mist known as the haar—a layer of bad mood and gray that shifts in from the North Sea. And then, just as suddenly, malicious skies, homicidal gusts, and soaking rain can turn into an afternoon of blissful blue.

The knee-biting climb up—via narrow, twisting stairways—culminates in a sense of Edinburgh’s scale and proportion, of its distinctive parts, its hills and its numerous phallic monuments (including the towers and follies up on Calton Hill—for centuries a popular cruising area). 

It’s not a big city, and the visually arresting bits are mostly clustered around its center. Built on seven hills, Edinburgh is topographically wayward, undulating and lopsided, its peaks and troughs bestowing depth, dimension and lots of steps. Plus extinct volcanoes—including the craggy plug that Edinburgh Castle sits upon. Trading on its weathered looks, Edinburgh somehow perfectly embodies a country whose national animal is the unicorn.

Historic Edinburgh is split in two, with a great big chasm in the middle—a gutter funneling the train lines through the city’s heart.

South of the chasm, medieval Old Town unfolds like a cobbled wonderland at the foot of Castle Rock. On the northern side, though, there are straight streets and orderly Georgian terraces. The two halves both have their secrets.

Descending the monument’s tight stairwells, I nip across Princes Street and dip into streamlined New Town. It’s every bit as spacious and orderly as it was in the 1700s, when it was laid out in polite rows—a reaction to the medieval squalor and overcrowding of the existing inner city where waste was tossed into the streets. Some joke that this was what gave Edinburgh the nickname “Auld Reekie”—in the 18th century, it stank.  

New Town was designed with grand Georgian terraces, manicured gardens and, on George Street, stately bank buildings, many of which are now hotels, bars and restaurants. More drinking holes are crammed into pedestrianized Rose Street (once rife with prostitutes—aka “roses”) than anywhere else in Edinburgh. Dirty Dick’s sounds promising, so I poke my head inside. But instead of a gay bar it’s crammed with memorabilia and regulars nursing pints, much as they’ve been doing since 1859. Nearby, on South Castle Street, I make small talk with farmers and microbrewers at an artisan food market, then over to Thistle Street to drool over the merchandise at 21st Century Kilts. Proprietor Howie Nicholsby is one of those designers who has successfully put a contemporary spin on Scottish clichés. He’s designed man-skirts for Lenny Kravitz, Alan Cumming and Vin Diesel (gosh!), playing on the sex appeal of leather, camo, denim—even tartan. 

Another place that is rip-roaringly up-to-date is Tigerlily, a crazy-beautiful boutique hotel in one of George Street’s former banks—it’s festooned with glitter balls and Alice In Wonderland-sized furniture. You could spend the night studying its décor and outré color schemes. But I’m catching up with friends for pre-dinner drinks, so we’re trying a few of the menu’s “masculine” concoctions, including the Gentleman’s Agreement, described as “lip-puckeringly tasty” and mixed with intent by manscaped barmen. 

For dinner, we grab taxis for the 10-minute ride to Prestonfield, a decadent estate hotel owned by James Thomson, one of Edinburgh’s most prominent gays. 

Thomson spent £3 million restoring the 17th-century mansion to create the city’s most opulent 21st-century hideaway. As you head down the long approach avenue at the edge of Holyrood Park, it’s like dipping into the countryside, its vast grasslands stocked with big-horned, shaggy-haired Highland cattle.

Steeped in antiques and auction-rescued artworks, Prestonfield basks under layers of velvet and elaborately patterned wallpapers. Benjamin Franklin, Winston Churchill, Sean Connery, Elton John and Catherine Zeta-Jones have all raised the roof here in their own ways—it doesn’t get more A-list than this. Decadence is nevertheless tinged with bohemian quirkiness in the way of Moulin Rouge—it’s flamboyant, swanky and quixotic, though the highlight is the team of young butlers in kilts.

Two wood-paneled oval rooms serve as Thomson’s celebrated Rhubarb Restaurant, where we’re plied with expensive food and wine and fawned over by delicious waiters who,  even by the end of the night, stubbornly refuse to resolve that old conundrum by lifting their kilts.

Within walking distance of Prestonfield, 94DR is my guesthouse on Dalkeith Road, owned by Paul Lightfoot and John MacEwan. Their friends call them “high-octane gays,” and they’re energetic, meticulous hosts. 

Sidestepping doilies and dusty antiques, the house’s historic bones are vitalized by chic-minimalist touches—white chandeliers against a backdrop of charcoal and gray, and a slick chill-out lounge, where music spills from an iPod docked next to a pair of iPads, DIY Nespresso machine and honesty bar. Upstairs, in Bowmore—the best of the six rooms—slightly creaky wooden floors under plush carpets are a reminder that the original bones are still there. I slip between warm silk-soft linens and drift away listening to the rain and dreaming of men in kilts.

Setting off early for the Salisbury Crags, an energetic walk through sodden, heathery grass lands me on Arthur’s Seat, Edinburgh’s landmark hill and a magnificent vantage point. Up here, the chilly air shooes away any sign of hangover, and as the early-morning sun turns the city aglow, the 360-degree views put a lump in my throat.

Back at 94DR, Paul is juggling duties as chef and morning raconteur, dishing up local gossip in his delicious accent while serving kiln-smoked trout and salmon from Loch Fyne. His commentary spans everything from the city’s best restaurants to the latest political hoopla. 

I’d happily kill the day listening to my hosts, but they’ve given me a list of places to sample, so I set off to connect with Old Town. There, bordering Holyrood Park, at one end of the Royal Mile, is the Palace of Holyroodhouse—where the queen stays when she’s in town. And it’s directly across the road from one of the city’s modern curiosities, the Scottish Parliament. 

Get the details on where to “Stay, Eat, Play & Be Mary” with our Edinburgh Springpad Notebook at instinctmagazine.com/travel