Four days in Tallinn: a medieval trading town, fifty years behind the Iron Curtain

Come in through Viru Gate, which is what is left of the fourteenth century gatehouse: two round towers with conical roofs, a flower market in front of them, and the whole of the medieval town behind. This is the merchants' and artisans' half, the All-Linn or Lower Town, as distinct from the hill where the nobility and the bishop lived and looked down on them. It is also the busiest part of Tallinn by a long way, so the earlier or later you walk it the better it is.

Town Hall Square opens out five minutes in. The Gothic town hall on its south side is the only one of its kind left standing in northern Europe, finished in 1404, with an arcade at ground level and a weathervane of a medieval guard on the spire that the city has adopted as a mascot. The square was the marketplace, the site of the executions and the place where the Christmas tree tradition may or may not have started in 1441, a claim Riga disputes with a date of its own. The cafés around the edge are priced accordingly.

Finish at Niguliste, St Nicholas's church, at the other end of the lower town. It was the German merchants' parish church, it was gutted by Soviet bombing in March 1944 and burned again in the 1980s, and it was rebuilt as a museum rather than a working church. What is inside is the reason to come: Bernt Notke's Dance of Death, painted in Lübeck in the late fifteenth century, showing a pope, an emperor, a cardinal and a king being led away by skeletons. Only the first seven and a half metres survive. It is the finest medieval painting in the Baltic states and there is almost never a queue for it.

Toompea is the limestone hill the whole town grew under, reached by two lanes called the Long Leg and the Short Leg, which were gated against each other because the hill and the town below it were separate jurisdictions that did not always get on. The upper town was the bishop, the knights and later the Russian governor. The lower town was the money.

Alexander Nevsky Cathedral is the first thing at the top, and it was built between 1894 and 1900 to make a point. This was the Russification period, and putting a full onion domed Orthodox cathedral directly opposite the seat of government, on the highest ground in the city, was not subtle. Independent Estonia debated demolishing it in 1928 on the grounds that it was a monument to oppression and did not suit the skyline, and lost the argument. It survived the Soviet period too, and is now the busiest Orthodox church in the country.

Directly across the square is the Toomkirik, St Mary's Cathedral, and it is the older and quieter building by six and a half centuries. Founded in 1229, Catholic then Lutheran from 1561, it is the burial church of the Baltic German nobility, and the walls are covered floor to ceiling in carved wooden coats of arms of families who ran this country for seven hundred years and then left in 1939. Climb the tower if it is open. Behind the cathedral, the Kohtuotsa and Patkuli platforms give the view of the lower town roofs that is on every photograph of Tallinn, and both are free.

Come down in the afternoon to Vabamu, at the foot of the hill by Freedom Square. It covers 1940 to 1991: the Soviet occupation, the German occupation, the deportations to Siberia, the deportations again, life under the second occupation, and the singing that ended it. It is a museum built by people who lived through this, and the section of recorded testimony is the part that stays with you. Two hours.

St Olaf's is the tall dark spire at the north end of the Old Town, begun in the twelfth century and rebuilt repeatedly because lightning kept hitting it and burning it down. There is a claim, endlessly repeated here, that at one point in the sixteenth century it was the tallest building in the world. It is now a Baptist church, which is an odd fate for a Hanseatic landmark, and it spent the Soviet decades with a radio mast and a surveillance post on the top, watching the harbour. You can climb the tower between spring and autumn: it is a hundred and twenty odd metres of narrow spiral staircase and the platform at the top runs right around the spire.

Walk north out of the walls into Kalamaja. It is the oldest suburb in the city, fourteenth century in origin, named for the fish houses that stood here, and it was a workers' district of one and two storey wooden apartment buildings, most of them thrown up around 1900 for factory hands. Nobody with money lived here for a century, which is why it survived, and it is now the best part of Tallinn to simply walk around: painted timber facades, tiny front gardens, a park where the railway used to be, and the Telliskivi complex of old rail workshops full of bars, studios and the flea market.

The Seaplane Harbour is fifteen minutes further, on the water. Lennusadam is a hangar built in 1916 for the imperial Russian navy's seaplanes, and the three shell concrete domes were an engineering feat at the time, poured without internal supports. The museum inside is the best in the country. The submarine Lembit, British built in the 1930s for the Estonian navy, sits on the floor with its hatches open so you can go through it. There is a sixteenth century wreck, a collection of seaplanes hanging overhead, and moored outside in the harbour the steam icebreaker Suur Tõll, which is also open.

Kadriorg is twenty minutes east on tram 1 or 3, and it is where Tallinn goes when it wants trees. Peter the Great had the palace built from 1718 by the Italian architect Niccolo Michetti, named it for his wife Catherine, and then declined to live in it, preferring a modest cottage in the grounds which is still there and still open. The palace is a small pink and white Baroque box with a genuinely grand main hall, and it now holds the foreign art collection: Dutch, German and Russian paintings, well hung and rarely crowded. The park around it runs to ninety hectares, with a formal flower garden, a Japanese garden and a swan pond.

The tram back drops you within a few minutes of the ferry terminals and the station, so this works as a departure morning as long as you are not flying before lunch.