Free self-guided itinerary. This is a travel guide, not a bookable guided tour.
Tallinn’s old town is roughly 800 metres across. That means a self-guided walk here can afford to be thorough in a way that is impossible in a larger city — this loop is about 2.5 km and covers most of what is worth seeing.
The climb is placed early, while you still have the legs for it.
Start: the Viru Gate towers, the usual entrance to the old town from the modern city.
Go through and bear left rather than following the main flow straight ahead. The lanes on that side are narrower and quieter and bring you into the Town Hall Square from a corner rather than head-on, which is a much better first sight of it.
The town hall itself is the oldest surviving one in northern Europe. The square in front of it was the market, the court and the place of punishment, all at once.
Leave the square to the west and climb by Lühike jalg (“short leg”), the stepped passage, rather than the longer road. Both were gated: the upper town and the lower town were separate jurisdictions and locked themselves apart at night.
At the top, the large onion-domed Alexander Nevsky cathedral faces the parliament building — it was built at the end of the nineteenth century as a deliberate political statement and is still read as one locally.
The medieval Estonian cathedral is a short walk away and is a very different building: plain, whitewashed, full of memorials.
Then take both viewing platforms on the edge of the hill. One looks over the red roofs and spires of the lower town towards the sea; the other looks north-west over the walls and towers. They are two minutes apart and both are free.
Descend by the longer passage, Pikk jalg, which brings you out at the top of Pikk street — the merchants’ street, lined with guild halls and the tall narrow houses of the traders, several still showing the hoists used to lift goods into the roof stores.
Follow it north to the city wall and the squat round tower at the seaward gate.
Turn south and return through the lanes east of Pikk, past the longest surviving stretch of wall with its towers. You come out near where you started.
The single biggest factor in how the old town feels is whether cruise ships are in port. If the Town Hall Square is full by mid-morning, walk this route backwards: start at the walls, do the upper town late, and reach the square in the early evening after the ships have sailed.
The cobbles are large, rounded and uneven — this is the single most common complaint from visitors and it is entirely a footwear problem. Public toilets are scarce inside the walls. Card payment is accepted essentially everywhere, including for very small amounts.
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