Naissaar exists in history because of Tallinn. The island shelters the city’s bay from the open gulf; whoever held Tallinn fortified Naissaar, and whoever wanted Tallinn landed there first. The city itself — Reval to its Hanseatic merchants — is one of the best-preserved medieval towns in northern Europe and a UNESCO World Heritage Site.
Almost every visitor to Naissaar sleeps in Tallinn before or after, so the Old Town is the natural other half of the trip: a morning of towers and merchant houses, a day of forest and sea.
Top things to do: Tallinn Old Town
Town Hall Square
The Gothic Town Hall has presided over Raekoja plats since the early 15th century. The square is the centre of the Lower Town, ringed by merchant houses and café terraces.
Toompea and the viewpoints
Climb to the Upper Town for the castle, the cathedrals and the viewing platforms. From here you look over the red roofs to the harbour and, on a clear day, to the long dark line of Naissaar across the bay.
Walk the walls
Long stretches of the medieval city wall and many of its towers survive. Kiek in de Kök, the great artillery tower, houses a fortifications museum.
Take a guided walk
A two-hour Old Town walking tour is the quickest way to get your bearings; Soviet-history walks and bike tours go beyond the walls.
How to get to Tallinn Old Town
- From the harbour: the Old Town is 10–20 minutes’ walk from the passenger port and the seafront piers used by island boats.
- From the airport: Tallinn airport is only about 4 km from the centre; trams and buses take around 20 minutes.
- From Helsinki: ferries cross the gulf in about two hours, many times a day.
Insider tips
- Do the Old Town on your arrival afternoon and keep a whole day free for the island.
- Buy picnic supplies in Tallinn the evening before you sail — the Balti Jaam market near the railway station is ideal — because there are no shops on Naissaar.
- Cobbles are hard on feet: wear the same sturdy shoes you plan to take to the island.
Best tours & tickets: Tallinn Old Town
These experiences are the easiest way to see Tallinn Old Town:
Walking tour from €35 Tallinn: Guided Old Town Historical Walking Tour
The classic introduction to medieval Tallinn and, by review count, the walking tour most visitors choose. Do it on the afternoon you arrive, and keep a full day free for the island.
- Town Hall, Niguliste and Kiek in de Kök with a guide
- Upper and Lower Town in two hours
- The most-reviewed Tallinn walk on our list
Bike tour from €31 Best of Tallinn 2-Hour Bike Tour
An easy guided ride to the main sights outside the Old Town walls, including the seafront. A good way to get your cycling legs back before a day on Naissaar’s forest roads.
- Seaside promenade and Kadriorg Palace
- Gentle pace on mostly flat ground
- Covers more of the city than a walk
Walking tour from €30 Hidden Tallinn: Soviet Walking Tour
A well-reviewed, inexpensive walk through the Soviet layer of the city. It is the natural companion to Naissaar, which spent the same decades as a closed military island that ordinary Estonians could only look at from the shore.
- Soviet-era architecture and everyday spaces still in use
- Stories from the occupation years
- Beyond the usual Old Town route
Ferry ticket from €43 From Tallinn: Return Day Trip Ferry Transfer to Helsinki
A return ferry ticket for a do-it-yourself day in the Finnish capital. The shipping lane to Helsinki runs out of Tallinn Bay past Naissaar, so in good weather you get a free look at the island from the deck.
- About two hours each way on a Tallink shuttle
- A full day on your own in Helsinki
- More than two thousand reviews
