The Old Town is the heart of Tallinn. This compact and largely pedestrian area is an enchanting, atmospheric and often confusing mix of medieval churches, soaring steeples, towers, cobblestone alleys, medieval warehouses and gabled merchant houses. The whole area was once completely walled, with stretches of those walls and 26 towers still seen today. You will likely lose your bearings navigating the winding streets and interconnecting passageways, but that is all part of the charm. Let yourself get lost and you will find yourself drifting through centuries of history.
Significant attractions in the Old Town include Tallinn City Museum and the St. Nicholas Church, which holds an excellent collection of medieval artwork. It is worth walking up to the castle district of Toompea Hill for views across the rooftops of Old Town and across the Baltic Sea. The hill is also home to one of Tallinn’s most iconic sights, the onion-domed Alexander Nevsky Cathedral.
One of the most pleasant things to do, however, is to just relax in one of the many unique cafes that line the streets of Old Town. The main square is filled with cafes and restaurants, but they tend to be busy and expensive. A far better idea is to duck into one of the smaller places on the side streets: Café Chocolaterie Pierre and its sister business, Café Josephine, are highly recommended.