
The landmarks in every guidebook — and the tours that tell you what guidebooks don't.
Tallinn has been at the northern end of a trade route since the Danish king Valdemar II showed up and conquered it in 1219, and the city has spent most of the time since being sold, occupied, and contested by Danes, Germans, Swedes, and Russians before the Estonians got it back in 1918. The 14th-century town walls with their 66 towers are better preserved than almost any medieval fortifications in Europe, partly because Tallinn was a backwater during the centuries when other cities were tearing their walls down to build suburbs, and partly because the city understood that those walls were the thing. The UNESCO-listed Old Town is the most coherent medieval urban environment you will find anywhere in northern Europe.
The Toompea, the limestone plateau rising above the old town and now home to the Estonian parliament, divides the city between the hill where the bishops and nobles lived and the lower merchants' quarter around the Town Hall Square.
The Town Hall, built in the 15th century, has a weathervane figure called Old Thomas on its spire that has been watching the square since 1530. The Maiasmokk cafe on Pikk Street, which has been serving coffee and marzipan since 1806, claims to be the oldest cafe in Estonia. The marzipan here is not an import: medieval Tallinn was producing it for export to the Hanseatic cities when it was still considered a medicine.

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4.8 across the App Store and Google Play. Here's a few we keep coming back to.
This tour was such a great way to see the city. The stories were interesting without feeling too scripted, and I loved being able to explore at my own pace.
This was a solid way to get to know Brighton without feeling like a tourist. The narration had depth and context, but didn't overdo it.
Started this tour with a croissant in one hand and zero expectations. The app just vibes with you, no pressure, just you, your headphones, and some cool stories.