Tallinn is a city designed for long, cold winters. The medieval streets are cluttered with cafés serving thick hot chocolate and gooey cakes; apple dumplings laced with cinnamon; pastries laced with rich, sweet jam or oozing cream cheese; sweet breads topped with nuts and raisins and slabs of home-made cake: lemon, orange, carrot, chocolate, all washed down with strong, dark coffee.

Cafés and shops are tucked away in tiny basements, with doorways so low that you have to bend double to walk in to them. Cobbled streets twist between buildings dating from the 14th century, restored and repainted in varying colours, giving the medieval old town a well-to-do, jolly air that contrasts strongly with the grey Soviet architecture that dominates the new town.

The best way to see Tallinn is a day of strolling punctuated with café-stops. At Maiasmokk (Pikk 16) cakes and marzipan have been made for two centuries. Head for the dark wood panelling and polished tables of the café for coffee and ounapomm (spiced apple dumplings).

More up to date is the Café Anglais (Raekoja plats 14), which overlooks the main square and boasts live piano jazz on some evenings. The hot chocolate, made with melted chocolate bars, has to be sipped to be believed.

Kehrwieder (Saiakang 1) is a dimly lit, couch-filled den, run by the same people as Tristan ja Isolde (Raekoja plats 1), a tiny café hidden away in the 14th-century town hall which serves 12 types of coffee to a smooth jazz soundtrack.

Snow has already started to fall in Tallinn and the city’s Christmas market (Nov 30 to Jan 4) is ideal for light shopping between coffee stops.

WHAT ELSE?

At the top of Toompea Hill stands Alexander Nevsky Cathedral, with its distinctive onion-bulb towers. Outside the church is imposing, while inside it is simply beautiful, with mosaics, frescoes and gold-clad icons.

Shopping in Tallinn can be frustrating: souvenir shops adopt hard-sell tactics over amber jewellery, babushka dolls and questionable knitwear. Instead head to Katarina Kaik, where a group of artisans have formed a guild of shops-cum-studios, where you can see them at work. Ceramics, glassware, jewellery and quirky sculpture are all on offer.

FOOD AND FUN

If you want to eat Estonian, avoid the naff medieval-themed restaurants such as Olde Hansa and Peppersack, and head instead to Vanaema Juures (Rataskaevu 10). Translated as Grandma’s House, the restaurant combines old family photos, comfy chairs and dim lighting with a traditional menu including roast elk.

Kick off a night out at Pegasus (Harju 1), and perch on a Venus bar stool, nibbling on sushi and slinging back a Cosmopolitan or two. Moskva (Vabaduse Valjak 10) offers the chance for a shimmy when the DJ gets going.

If you’re feeling brave, try McCools (Suur-Kaja 20), so vast that there are 70 seats along the bar. McCools shares a building with the Stock Exchange; drink prices fluctuate along with the currency. Watch the giant TV screen to buy at the right price.

WHERE TO STAY

The Three Sisters (0800 1698817, www.designhotels.com) is housed in three connected buildings dating back to the 14th century. The minimalist decor, juxtaposed with medieval wooden beams and sloping floors, gives it a quirky feel. At weekends doubles start at £138.

The Schlossle Hotel (00 372 699 7700, www.schlossle-hotels.com ) offers log fires and comfy sofas, with a restaurant in 13th-century vaults. Rooms start at £121 in December.

NEED TO KNOW

Estonian Air (020-7333 0196, www.estonian-air.ee ) operates direct flights from Gatwick to Tallinn. Returns from £161. For packages, try Regent Holidays (0117-921 1711, www.regent-holidays.co.uk), Travelscene (0870 7779987, www.travelscene.co.uk) and Scandinavia Freestyle (020-8846 2666, www.norwegiancoastalvoyage.com).

READING

Baltic Capitals (Bradt, £11.95). Tallinn in Your Pocket is available from tourist offices and hotels.

ANNABELLE THORPE