Oh dear. I'm in the Estonian capital on a recommendation and was led to believe all would be charming. I sit back and sigh, watching my breath almost freeze. It feels like no-man's land. Then, out of nowhere, the outline of medieval turrets rises above the city's old quarters as arterial roads give way to 13th-century cobbles – the reason people come here becomes obvious.
Only 15 minutes from the airport and you're in a Baltic fairytale. In fact, Tallinn's Disney-like old town, thought to be the best preserved in the world, was rightly declared a Unesco world heritage site in 1997.
The place might have been designed with winter in mind, its architects intent on creating a city that comes into its own when afternoons draw in and there's an excuse to festoon buildings with lights. There's a sense of stepping back in time as you mooch around the alleys, strolling past gabled houses and half-hidden courtyards. Cavernous cafs fogged by steaming milk lurk enticingly on every corner; and if you want to see the view that adorns boxes of chocolates, walk up to the elevated vantage point and take in a panoply of russet rooftops, Gothic spires, the vertiginous TV tower built for the 1980 Moscow Olympics and the harbour ferrying in Finns from Helsinki, two hours across the Baltic Sea.
Next morning I'm met at my hotel by a charming couple, Eva-Maria and Indrek – young entrepreneurs in fur hats, armed with a wealth of knowledge. Booked on a personal tour covering the city's Soviet legacy, I fold myself into their 1980s Lada and am shown the surviving landmarks of that dubious epoch. Estonia gained independence in 1992 but for most of the 20th century was in the Soviet Union.
We pass the old KGB headquarters where unfortunate individuals were shot or sent to exile in Siberia; visit the grisly, derelict carcass of Paterai, a waterfront prison; plus I'm shown around a makeshift statue graveyard that houses the toppled remains of giant granite Stalins. I also spend a strangely thrilling hour firing guns with real ammunition in an indoor shooting range. Instructor Tonu looks as deadly as the cartridges littering the floor but his patient instruction soon has me wielding an AK-47 like a pro. I can't say what smelt the most – the gunpowder or testosterone.
Back in the car, Eva-Maria tells me she is the daughter of Harry Egipt, the country's most famous film producer. In the Seventies and Eighties, his all-singing, all-dancing TV commercials sold Soviet housewives everything from washing powder to minced chicken. Genius examples of their type, they're as kitsch and wildly dated as you might imagine, and were recently revived for the titles of Borat.
As we watch them on a laptop, it's obvious how far this country has come. Tallinn is a city on the rise, with an educated workforce and an overwhelming desire to be modern. Estonia also wants to be known as a Nordic state rather than an eastern European country, and the proliferation of cool blondes staffing hotel receptions and world-class restaurants reflects this. While not every girl here is quite as desirable as local model Carmen Kass, stag parties still descend on the city looking for beer, love and everything in between.
If it's wenches you're after, visit Olde Hansa, a sort of medieval Hard Rock Caf that swaps burgers for bear steaks and employs staff straight out of The Canterbury Tales (with a Carry On twist). Eateries veer from the rustic to the sublime, but try modern Estonian at Mekk in the Savoy Boutique Hotel for gourmet soups and clever ways with lamb.
On my return home, an old woman serving food at the airport caf cracks her knuckles and eyes me contemptuously. "You have to order butter in advance," she booms in faltering English. I get dry bread as thick as a doorstep, and rich mushroom soup garnished with dill. It's delicious. Madam Brezhnev looks at me devouring every spoonful and grins from ear to ear. She's probably thinking: "I bet he doesn't get that in Gatvik."
The facts Flights from Scotland to Tallinn from 136 return, see www.skyscanner.net; Merchants House Hotel from 95 B&B for doubles, suites from 79. www.merchantshousehotel.com; Estonian Experience: The Soviet Legacy Tour costs from 50pp, www.estonianexperience.com; Olde Hansa, Vana Turg 1, Tallinn (www.oldehansa.com, 00372 627 9020); Savoy Boutique Hotel, Suur-Karja, Tallinn (www.savoyhotel.ee, 00372 680 6688); www.tourism.tallinn.ee)
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This article was first published in Scotland on Sunday, January 31, 2010