Tallinn is small, walkable and easy, and its medieval Old Town is so complete that many visitors never leave it. That would be a mistake. The best trips pair the cobbled lanes and towers with the city outside the walls: the Seaplane Harbour, the Soviet-era history told at Vabamu, the palace park at Kadriorg and the food and drink of Telliskivi. Here is how to plan a first visit.
How many days
Two full days cover the essentials comfortably; three let you add Kadriorg, the TV Tower and a slower evening or two. Many visitors arrive on a day trip from Helsinki, about two hours away by ferry; a day is enough for the Old Town and Toompea, but stay overnight if you can, because the walls and towers are at their best when the day-trippers have gone.
What to book ahead
Very little in Tallinn sells out, but a few things are worth securing. Book the TV Tower for a timed skip-the-line slot on a clear day. If you plan to see both maritime museums, buy the combined Seaplane Harbour and Fat Margaret ticket. The Vabamu and KGB Prison Cells combination is the best way to do the twentieth-century history in one morning. The KGB museum at the Hotel Viru is guide-only and must be booked in advance. For dinner on Friday and Saturday, reserve the popular Old Town and Telliskivi restaurants. If you will visit several museums and use public transport a lot, compare the Tallinn Card, sold for 24, 48 or 72 hours, which includes transport and entry to many sights.
Watch the closing days
Mondays are the trap. The Seaplane Harbour, Kumu and the Kadriorg Art Museum close on Mondays, and the KGB Prison Cells close on Mondays and Tuesdays. Put the Old Town walk, Toompea and Telliskivi on a Monday and keep the museums for other days.
Getting in
From the airport, the tram runs into the city centre, and taxis and ride-hailing apps such as Bolt, which was founded in Estonia, are inexpensive by Nordic standards. Ferries from Helsinki and Stockholm dock at the passenger port, a short walk or taxi ride from the Old Town. Trains from the rest of Estonia arrive at Balti Jaam, next to Telliskivi.
Getting around
Walk the Old Town, Toompea, Kalamaja and Telliskivi; everything is within about twenty minutes on foot. Use trams for Kadriorg and buses or taxis for the TV Tower and Pirita. Public transport tickets can be bought by app or with a smart card, and the Tallinn Card includes travel. Wear shoes with grip: the cobbles are slippery in rain and treacherous in ice.
Day one: the medieval city
Start early at the Viru Gate and walk to the Town Hall Square. Follow Pikk Street past the Great Guild Hall, where the Estonian History Museum gives you the long view, to Fat Margaret at the sea gate. Return through Lai Street and the lanes by the walls, then climb to Toompea by the Long Leg for the Kohtuotsa and Patkuli viewing platforms, the Dome Church and the Alexander Nevsky Cathedral. Come down the Short Leg and have dinner in a vaulted Old Town cellar.
Day two: history and the waterfront
Begin at Vabamu for the story of the occupations and independence, then walk to the KGB Prison Cells on Pagari Street. After lunch, walk through Kalamaja to the Seaplane Harbour for the submarine and the icebreaker, then spend the evening at Telliskivi Creative City and the Balti Jaama market.
Day three: parks, art and the high view
Take the tram to Kadriorg for the palace, the park and Kumu, then continue to the TV Tower for the view across the city and the Gulf of Finland. Finish at Pirita beach for sunset if the weather allows. With more time, the Estonian Open Air Museum on the western edge of the city shows rural Estonian life in old farmsteads, windmills and a wooden church.
Seasons
Summer brings long, light evenings and the most crowds, especially when cruise ships are in port. Winter is cold and dark early, but the Old Town under snow and the Christmas market on the Town Hall Square are magical. Autumn and spring are quieter and good value.
Money and manners
Estonia uses the euro, cards are accepted almost everywhere, and service is often included or rounded up rather than tipped heavily. English is widely spoken, especially by younger Estonians.