Stepping inside the walls of the old town in Tallinn is like being transported back in time. Cobbled streets, gothic buildings and slender spired churches abound as well as the best preserved medieval town hall and square to be found anywhere in Europe.

We were lucky enough to be staying in the beautiful Three Sisters Hotel on Pikk Street. Listed in most guide books as an essential building to view from the outside, the current owners of these three merchant houses dating from 1362 have created a 5* boutique hotel experience that rivals the best in the world. Past guests have included luminaries as diverse as Queen Elizabeth 2 and Lou Reed. As soon as you step outside the Three Sisters onto Pikk street you are immersed in the history of Tallinn and Estonia. Just across the street “Fat Margaret’s Tower”was built in the 16th Century to serve as a cannon platform and ammunition depot, and today is home to the Estonian Maritime Museum, an essential stop to appreciate the importance of the port on the history of the town.

More recent history is remembered in a plaque outside the current childrens’ library directly beside the hotel. It was in this building that the KGB set up headquarters for some of the period of Soviet occupation which started during the second world war and ended in 1991. After Estonians regained their independence they were quick to sweep aside the Lenin statues and other remenants of the regime but half a century of history did leave its mark. A visit to the Museum of Occupation and Fight for Freedom is highly recommended to get an idea of what life was like during this repressive era.

The city walls themselves no longer circle the city in an unbroken ring but there are some remarkably well preserved stretches with over twenty gates and red-roofed medieval towers making for a stunning sky line. A handful of these towers have been restored and are open to the public. We happened into “Asuur” in a tower on Laboratoorumi Street which houses artists workshops and showrooms. If you want to delve deeper into the history of Tallinn’s fortifications a visit to Epping Tower is a must; in addition to exhibits that tell the full story you can even try on some armoured chain mail. “Kiek-in-de-Kok” tower got its name from the fact that that when the tower was built in the 16th century the soldiers manning the cannons had a birdseye view into the kitchens of the houses below. The literal translation is “a peek in the kitchen”. Visitors to the museum housed here today will see examples of impressive medieval firepower as well as a fascinating exhibit on crime and punishment in old Tallinn. Don’t leave Kiek-in-de-Kok without joining a guided tour of the tunnels running under the old bastions at the southern edge of Toompea Hill.

There’s plenty to do outside the old town too. The leafy landscaped Kadriorg Park is where Tallinners flock to escape the city in summer. For visitors to Tallinn, it’s possible to spend a full day here with a wealth of things to see and do from KUMU Art Museum, Kadriorg Palace built for Peter the Great and his wife Catherine, Peter the Great’s cottage where he lived from 1714 to 1716 supervising the administration of his newly conquered Baltic provinces and The Rusalka Memorial, an imperious angel wielding a gleaming cross erected in 1893 to commemorate the sinking of a Russian warship.


Eating and drinking around Tallinn is a pleasure. A cinnamon beer accompanied by a dried elk meat snack at “Old Hansa”  is the perfect way to replace lost sightseeing energy. Lit completely by candle light and set right on the edge of the old town square this is a medieval theme bar that gets it right. On the other end of the cool scale don’t miss DM Bar, a place dedicated to all things Depeche Mode and they don’t play music by any other band.

We ate at Von Krahli Aed, a lovely laid back place focusing on Estonian food with a slight modern twist and Ribe which again has a fresh take on Estonian classic and is aimed more at the fine dining end of the market. Both great choices and there’s plenty more to choose from. A Tallinn Card is a good investment if you’re planning a lot of museum vists and it also gives you free access to public transport. You can find out more at the Tallinn Tourist Board.

Strange as it might sound a trip to Helsinki is an essential part of any weekend in Tallinn. There are several scheduled ferry crossings every day and the trip is just two hours. Look out for our city review of Finland’s capital city later this week.