As you stroll around Tallinn, you realise that you're in a place where history hasn't just happened – it has left a lasting mark. The result is that the Estonian capital, which will be European Capital of Culture in 2011, is actually two towns, one wrapped around the other.

There's the quaint old town whose battlements serve to remind visitors of past invasions, not to mention the structures within it that still bear the wounds of devastating Second World War bombings. Graffiti remains from what Estonians soberly call "the Soviet times".

Then there's modern-day Tallinn, a thriving and vibrant metropolis with restaurants serving fine food in a laidback outdoor setting, antique shops that are ripe for browsing, packed-out clubs and a sophisticated tourism infrastructure that even fields a company offering glamorous vintage cars for daily hire.

By virtue of its history, Tallinn is a place of contradictions and the melting pot of Russian, Baltic and Scandinavian influences creates a slightly eccentric but undeniably engaging destination. Located on the Baltic coast, with Finland visible on a clear day, the city is also just a few hours' plane journey from the UK. And with the airport just minutes from the city centre, it's about as hassle-free as a European weekend break can be.

Unlike Paris, Barcelona, or Rome, any of which you would be hard-pressed to see properly in four or five days, as a small city - Tallinn is home to a population of just 400,00 - two days is long enough to see all its highlights. After a weekend there, you can absolutely say you've "done" the city.

The Old Town is the main attraction and it's immediately obvious why it was awarded UNESCO World Heritage status in 1997. A filmmaker seeking the perfect location for a Hans Christian Andersen fairytale need look no further than Estonia's quirky capital.

Slightly reminiscent of Prague, the still-walled city has retained far more of its original infrasctructure than its Baltic neighbours and is all cobbled streets, colourful façades and brooding medieval architecture.

Certainly, its chocolate-box cutesiness, such as the 'traditional' wooden stalls selling wonderfully aromatic spiced almonds and gaudy marzipan delicacies, or waitresses dressed up as medieval peasants, can make you feel as if you have accidentally stumbled into Main Street at Disney World Paris.

But then a tour guide tells you about the strong-man contest that gave the watchtower its obscure name, points out the ancient well Tallinn residents once believed housed a malevolent witch and reveals how locals once dodged the city bylaws concerning murder to rid themselves of a troublesome spouse or cheating trader. Somehow the tourist trappings fade a little and the character and charm of the place emerges.

And it is charming. The views from the hilltop that dominates the skyline are magnificent: in one direction, the Old Town, and in another the sea.

Tallinn isn't about finding that one iconic landmark, nor does it boast the legacy of any great historical figures (or at least none Brits have heard of). But there are the fire-damaged remains of St Olaf's church, once Europe's tallest, an old town hall with a novel form of stocks once used to punish recalcitrant locals, and a still-operating 15th-century pharmacy with shelves of intriguing potions and preserved body-parts.

For quirkiness, it doesn't get much better than the Kiek in de Kök Museum - meaning "Peep in the Kitchen" - located under one of the old city walls and devoted to the history of these fortifications. A key exhibit focuses on the history of one ancient tunnel, from the earliest days when it was used by the military. In the 1990s, it provided shelter for homeless people (one of whom is now immortalised in waxwork form) while punk rockers used it as a studio during the Communist era.

When choosing accommodation, there are hotels inside and outside the Old Town but, since the best way to experience the city is on foot, it is a real advantage to stay in one of the many inside the city walls. The most luxurious and indulgent of these is the Schlössle Hotel, a stylish boutique hotel tucked away in a side street just minutes from the main square.

A member of Leading Hotels of the World, its rooms are modern but individual with large fireplaces, authentic wood-panelling and antiques. If you stay any time from spring to autumn, the quiet courtyard is perfect for breakfast, or for a pre-dinner drink, before dining in the hotel's fabulous Stenhus Restaurant. Which brings us to the subject of eating out: at times it's easy to forget how tucked away in Europe's far north-east Tallinn is, but one look at any menu will remind you of the city's Baltic/East European culture.

Estonian cuisine is heavy on the wild boar, hearty meat stews and bacon-stuffed bread rolls, while the Russian restaurants dotted about offer similar fare but with the inevitable vodka shot between (and during) courses.

As a vegetarian, I struggled to find anything non-meaty in the traditional restaurants, though I would recommend the Traditional Estonian cuisine served at the unpromisingly named Kuldse Notsu Kõrts (meaning Golden Piglet Inn) for the fabulously named "old witches stew" - a delightful cauldron of cheese, potato and mushrooms - and divine gingerbread ice cream. Although the menu in the hotel restaurant is also heavy on the meat, the chef is happy to prepare fish or vegetarian dishes on request.

And if you can't find anything veggie-friendly in the restaurants that serve the national cuisine, Tallinn also offers plenty of tourist fare. In the main piazza alone, you can find pizza, curry and baguettes.

One of the nicest surprises about Tallinn is that, unlike so many other capitals in the former Soviet Union, it has not become a stag-party destination, with all the drunken rowdyism that can entail.

The local police are strict in preventing groups of men from wandering around (especially those clad in pink wigs and football strip), while drinks are not especially cheap.

Compared with many East European capitals, Tallinn after dark is a remarkably pleasant place to stroll about in, even if the bars and clubs are a little self-consciously glamorous.

Weather permitting -and Estonia enjoys fairly temperate summers not unlike our own - Pirita Beach is a short drive away, although swimming in the sea, icy even on warm days, is for the brave only. Better to experience seaside Tallinn from a kayak and row right up to the magnificent submarine, the oldest still afloat in the world.

The newer part of town has little to offer beyond the gorgeously decorative rooms of Kadriorg Palace. Further afield, there are day trips to explore the forests around the city, or a ferry ride over to Helsinki.

With its stint as European Capital of Culture approaching, the city is looking to the future. Western shops are springing up across the Old Town and there are countless new projects on the drawing board, including the possible redevelopment of the port, which would allow the city to capitalise on its seaside location.

The risk is that by courting tourists, Tallinn may lose some of its individuality and charm and become just another holiday destination.

This also means Tallinn is a place to visit soon - either as part of a longer Baltic tour or just for a weekend city break. Otherwise, you run the risk of discovering that this quirky and charming city has been homogenised, just like so many other cities in Europe.

Getting there

Schlössle Hotel (www.schloesslehotel.com; 00372 699 7700) has deluxe double rooms from ¤198 (£169) per night, including breakfast. Estonian Air (www.estonian-air.com) flies from Gatwick to Tallinn on Thursdays and Sundays with return fares from £142. Kuldse Notsu Kõrts Restaurant (www.hotelstpetersbourg.com/notsu-restaurant.html). Kayaking tour (www.360.ee) costs ¤30 (£25.30) per person. Information on
Tallinn 2011 European City of Culture events is available from www.tallinn2011.ee.

Jewish Tallinn

● There are approximately 4,000 Jews in Tallinn.
● Estonia has had a documented Jewish presence since the 14th century, but Tallinn itself only had a substantial Jewish community from the 1860s.
● A synagogue opened in the centre of the new part of the city in 1883, with a mikveh, Jewish school and a cultural centre.
● Some 200 Jews are believed to have fought for Estonia during its War of Independence between 1918 and 1920.
● Many of Estonia's Jews fled to Russia during the Holocaust. Others were rounded up by the Nazis and died in the camps. The Old Synagogue was destroyed when the Russian army bombed the city.
● A new synagogue and community centre opened in 2000.

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