Whether approached by air, land or sea, Tallinn is immediately identifiable as a capital that looks to the West rather than to the East.

The departure board at the airport lists London, Copenhagen and Stockholm but rarely St Petersburg. The boats that fill the harbour, be they massive ferries or small yachts, head for Finland and Sweden, not Russia. The traffic jams that are beginning to block the main streets are caused by Volkswagens, Land Rovers and Audis, not by Ladas. Links with the West are celebrated; those with Russia are commemorated.

Tallinn was always ready to defend itself but in the end hardly ever did so. Only for 16 years, between 1561 and 1577, were its fortifications put to the test, when the Swedes, Danes and Russians all attacked the city. The nearest it came to what might have been a major battle was at the conclusion of the Northern War in 1710, but plague had reduced the population from 10,000 to 2,000 so the Swedes offered little resistance to the army of Peter the Great. Tallinn has suffered many occupations but, apart from a Soviet bombing raid in 1944, the city has not been physically harmed as no battles were ever fought there. Its fate was always determined elsewhere, in the 14th just as much as in the 20th century. Only after 30 years of independence is Tallinn firmly in its own hands.

Tallinn Estonia by Andrey Kutsenko Shutterstock
Architecturally, the Old Town has always remained the centre of Tallinn and is its main attraction © Andrey Kutsenko, Shutterstock

The division in Tallinn between what is now the Old Town on the hill (Toompea) and the newer town around the port has survived political administrations of every hue. It has divided God from Mammon, tsarist and Soviet governors from their reluctant Estonian subjects, and now the Estonian parliament from bankers, merchants and manufacturers who thrive on whatever coalition happens to be in power.

Tallinn has no Capitol Hill or Whitehall. The parliament building is one of the most modest in the Old Town, dwarfed by the town walls and surrounding churches. When fully restored, the Old Town will be an outstanding permanent monument to Gothic and Baroque architecture, and a suitable backcloth to formal political and religious activity. Outside its formidable wall, contemporary Tallinn continues to change rapidly according to the demands of the new business ethos.

Visitors returning to Tallinn who had previously been in the 1990s will today be surprised at how much time they want to spend outside the Old Town. Areas such as Telliskivi and Noblessner, both Soviet slums for all too many years after re-independence, are now each worth a day in their own right for their cultural and gastronomic diversity, highlighted by Fotografiska in the former and Proto in the latter. On the edge of the Old Town is the rejuvenated Rotermann Quarter. Its sleazy past was brought to life in 1979 by the film The Stalker, the last one made in the Soviet Union by Andrei Tarkovsky before he came to the West. Today, however, the area is keen to flaunt its luxury status, perhaps appropriately as it borders on Tallinn’s Wall Street.

There is a legend that, should Tallinn ever claim to be ‘complete’, the monster in Lake Ülemiste next to the airport, will flood the town. But now, more than ever, Tallinn continues to expand, outwards and upwards. 

What to see and do in Tallinn

Alexander Nevsky Cathedral

Entering the cathedral represents a symbolic departure from Estonia. No-one speaks Estonian and no books are sold in Estonian. It is a Russian architectural outpost dominating the Tallinn skyline and was built between 1894 and 1900, at a time when the Russian Empire was determined to stifle the burgeoning nationalistic movements in Estonia.

Alexander Nevsky Cathedral Tallinn Estonia by Grisha Bruev Shutterstock
The Russian influence on this cathedral’s architecture is clear © Grisha Bruev, Shutterstock

It was provocatively named after Alexander Nevsky, since he had conquered much of Estonia in the late 13th century. The icons, the mosaics and the 15-ton bell were all imported from St Petersburg. Occasionally plans are discussed, as they were in the 1930s, for the removal of the cathedral as it is so architecturally and politically incompatible with everything else in Toompea, but it is unlikely that any government would risk the inevitable hostility that would arise amongst the Russian-speaking population of Tallinn. 

Seaplane Harbour

Since the spring of 2012, one of the highlights of a visit to Tallinn has been the complex next to Patarei Prison, which opened in May that year. The basic structure of the hangars dates from 1916, when they were commissioned by the tsarist Russian government from a Danish company, Denmark being neutral in World War I. Such was the strength of the concrete with which it was constructed, that the building survived intact for the next hundred years and was happily exploited by each new army of occupation throughout the 20th century. 

Seaplane Harbour Tallinn Estonia by Visit Estonia
21st-century technology brings to Estonia’s early 20th-century history to life © Visit Estonia

There is an instant impression of 3D on entering the building, as it is necessary to look up, ahead and down at the same time to gauge the true effect of the collection. A walk begins on a bridge above most of the collection, in the air as it were, looking down on the boats at surface level and the submarines below it, with planes directly ahead and on both sides. 

Old Town Hall

This was the administrative and judicial centre of the town until 1970 and the extensive range of woodwork and paintings in the Council Chamber mainly reflects judicial themes. Six centuries of Tallinn’s history have been determined in this room and it is only since 1991 that its use has changed to a purely ceremonial role, with visitors allowed to tour and concerts taking place here.

Tallinn Old Town Hall Square by Tanel Murd Visit Estonia
Tallinn’s medieval grandeur still dominates in the Old Town; no conqueror or modern architect has dared to touch it © Tanel Murd, Visit Estonia

For much of this time, there were clearly ample funds in the public Treasury, as is shown by the opulence of the candelabra, the money chests and the size of the wine cellars. One of the carvings of David and Goliath on the magistrates’ bench is often taken to symbolise the relationship between Tallinn Council and its nominal masters on Toompea in the Old Town. 

Rocca Al Mare Open Air Museum

This deserves half a day to itself, ideally in balmy summer weather. The name (in Italian) means ‘cliff beside the sea’ and was given by the original owner of the estate when it was bought in 1863. The museum was founded in 1957 and opened to the public in 1964. It was the first such museum in the USSR and irreverent visitors at the time pointed out that it not only provided food for thought but food to eat as well. The descriptive panels throughout are in English.

Tallinn Open Air Museum Estonia by chasdeisgn, Shutterstock
The museum highlights all aspects of Estonian rural architecture © chasdesign, Shutterstock

It now consists of around 70 buildings and when complete should have a hundred. The aim is to show all aspects of Estonian rural architecture, with houses of both rich and poor. Most date from the 19th century but one of the chapels was built in 1699. The whole of Estonia is represented – windmills are from the island of Saaremaa but in contrast there are fishermen’s cottages from Lake Peipsi on the Russian border.