MORE than a quarter of a century ago I eked into Tallinn on the rickety old Soviet-style train from Warsaw and sought out one of the few tumbledown hotels.

I made my way through fairytale medieval, gothic and baroque streets that felt monochrome – bashed and unloved. Since then I’ve been on a journey with Tallinn. We’ve both grown older; Tallinn has weathered far better. Today it is one of my top city-break trips in Europe .

The Estonian capital is not somewhere that everyone can instantly place on a map. While fellow former Soviet cities like Prague and Budapest hog all our attention, Tallinn, tucked right up at the north eastern extremity of Europe on the shores of the Baltic Sea, remains more of a relative enigma.

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Some travel pundits have hailed the Estonian capital “The New Prague”, with its chocolate-box pretty old town and swathes of history. A valid comparison, but Tallinn remains defiantly, proudly Estonian. Until 1991, Tallinn was clamped under the confines of Soviet rule, but since it broke free, it has made up for the lost decades.

The National: Pride and defiance on the Baltic

Tallinn is indeed a mini Prague aesthetically and its compact size is all part of the charm, as its main attractions are within easy walking distance. Half the fun is just ambling around the cobbled streets drifting back through the layers of history at every turn. Russian Orthodox churches and Dominican monasteries share the streets with old merchant houses and medieval meeting halls: Hanseatic heaven.

The best place to get acquainted with Tallinn is from Toompea Hill. This castle district offers views of the old town’s winding streets and out over the Baltic Sea; often frozen over in winter. Serious money has gone into revamping Toompea’s impressive buildings and making it more visitor-friendly, with signposts, scenic lookouts and shops selling the work of local artists and craftspeople.

The epicentre of life is around the Old Town Square, the historic hub that stretches in a swathe of cobbles below Toompea. The square is home to the city’s tallest spire, which stretches into the heavens above the Old Town Hall, a spectacular sight floodlit at night. In the long, balmy summer months, pavement cafés spill out onto the cobbles.

The National: Pride and defiance on the Baltic

Breaking towards the sea from the Old Town Square is the thoroughfare of Viru, now something of a shopping Mecca. Gone are the days of food privations and long queues to buy simple items. Tallinn 2023-style is a land of plenty where the shops are stuffed with all the latest designer clothing, cutting-edge technology and all the other trappings of the 21st century.

Tallinn and Estonia impress and inspire in many ways. Scottish writer Lesley Riddoch has commented at length on the positive Estonian experience of independence and I chime with her concept of “Estonia, the Baltic Tiger”. The eponymous film she created is thought-provoking for anyone looking at comparisons with contemporary Scotland.

Outside the Old Town is the monument to the victims of the ferry disaster in 1994 that claimed the lives of 852 people when the Estonia ferry sank during a Baltic Sea storm. The cause of the disaster is still the source of some controversy in both Estonia and Sweden, but what is clear is that many hundreds of Estonians died in a black night for the fledgling Estonian Republic. When the Tartan Army are in town, we always play a bagpipe tribute here.

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Tallinn and the Tartan Army go back a long way. We had the infamous “game that never was” in 1997, when the Estonians never turned up and Scotland were awarded a short-lived 3-0 victory. The Tartan Army still love Tallinn. So much so that dozens of footsoldiers, including SNP councillor David Coutts, who I met out there once, jumped ship to ignite the local nightlife scene, kicking off with the Nimeta Baar (The Pub With No Name), then the Nimega Bar (bar with a name).

Times have changed. Today I breeze by the Nimeta and only see Irish, British and English flags flying, though I do find the Highlander Pub flying a Saltire nearby. In truth, Tallinn does not need anyone else to dictate her path as the city today offers one of Europe’s most compelling city breaks all by herself.

I end this visit at Fotografiska, a glorious reborn train depot that is now an impressive gallery. The rooftop restaurant won a coveted Michelin Green Star in May this year for its top-notch cuisine and sustainable ethos. I tuck into local lamb tartare from the island of Muhu spiced with chilli grown on their terrace and try my first-ever apple wine. All of it is utterly delicious.

Tallinn now also has a two-star Michelin restaurant, as well as a one-star – impressive for a country that only had its first Michelin awards last year. Estonia has really emerged as a serious foodie destination.

I gaze out over the train station after a faultless lunch. Slick modern trains ease in and out of the reborn station as I raise a toast to a city that has come a long – and deeply impressive – way.

Tourist information Finnair ( fly to Helsinki from Edinburgh, with Tallinn a half-hour flight onwards.