Toompea Castle Walking tours

Our most recommended Toompea Castle Walking tours

Tallinn: Medieval Walking Tour

1. Tallinn: Medieval Walking Tour

Walk through the narrow gothic dwellings, cozy cobblestone streets and well-made fortress walls with solid towers. The Old Town is comprised of two parts: Lower Town (residence of artisans and merchants) and Upper Town (residence of viceroys and the nobility). On this tour, learn how Tallinn got wealthy by attracting invaders and resisting them. Discover why Tallinn was known as a 'town of pepper and salt,' and how Estonians, local Germans and Catholic monks communicated with each other. Walking the cozy cobblestone streets, get acquainted with Tallinn history through interesting stories and legends.  See medieval dwellings from the 14th to the 15th-century, the oldest town hall and pharmacy in Europe and St. Olaf Church, having once been the highest in the world. Depending on your preference, visit a former Dominican monastery quarter taken over by female workshops of stain glass blowers, chocolatiers, artists, doll makers and weavers. Then, explore Upper Town - an area of German crusaders (later - noblemen), viceroy and bishops. See the largest Orthodox church in Estonia, then the oldest one in Estonia. Nearby, see Toompea Castle occupied by parliament. The climax of the excursion will be a visit to a viewing platform for a view of Tallinn. This excursion will finish at the Town Hall Square. You will also receive recommendations on where to try local food and drinks, what kind of souvenirs are worth buying, where to spend time with children and what museums are worth visiting.

Medieval Tallinn 2-Hour Old Town Walking Tour

2. Medieval Tallinn 2-Hour Old Town Walking Tour

Explore the Old Town of Tallinn and see monuments such as the remains of St. Catherine's Dominican Monastery. Step back to the Middle Ages and walk along Pikk Street, where the merchants' houses and craft guilds bring medieval Tallinn back to life. Get acquainted with the churches of the Holy Ghost, St Nicolas and St. Olaf as you explore the Lower Town and Upper Town. Discover why Tallinn is known as the town that limps on Lühike Jalg (Short Leg Street) and hear about the noble knights who lived in the Upper Town . Admire the outside of the Russian Orthodox Alexander Nevsky Cathedral and the Lutheran St. Mary’s Cathedral. Make your way to the ancient stronghold of Toompea Castle where the Parliament of Estonia now sits, and marvel at the Pikk Hermann (Tall Herman) tower that dominates the skyline. Get a fantastic view of the city from one of the platforms of the Upper Town. Return to the Lower Town on Short Leg Street to end on Town Hall Square.

Tallinn: Private Guided Walking Tour of the Medieval City

3. Tallinn: Private Guided Walking Tour of the Medieval City

Welcome to Tallinn! If you want to immerse yourself in the exciting present and the great past of this beautiful medieval Hanseatic city, then I would like to invite you to an individual German-speaking city tour.  You can explore one of the most beautiful and best-preserved late medieval cities in Europe on a 3- to 4-hour German-language walking tour, which is done individually - i.e. only for you as an ordered. You will get to know the fascinating lower town - the former Hanseatic city - with its merchant and patrician houses, the numerous churches, its winding streets and the impressive town hall square. The Domberg - also known as the Upper Town - impresses with its representative administrative and government buildings, parliament and embassies, the Orthodox Nevsky Cathedral and the Evangelical Cathedral Church.  From here, at the end of the tour, you will have unique views of the lower town with its city walls and fortification towers, modern Tallinn, the offshore islands and the surrounding Baltic Sea. During the guided tour you will not only immerse yourself in the history of Tallinn, in which the Germans occupy a special place, but also get information about the current situation of the country and its inhabitants.  Questions are very welcome! In addition, I am happy to give you practical information for a good café or a restaurant away from the tourist crowds, shopping or other "insider tips" - if desired. This tour is suitable for all ages. Breaks can be installed at any time on request. People with physical disabilities are welcome.

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What people are saying about Toompea Castle

The tour with Roman was great! We walked around the entire lower and upper city, looking into courtyards and stopping at individual buildings. Roman has thousands of stories, facts and legends in store! He skillfully weaves them into the outline of the excursion. The old city is like a precious box, and Roman, like an experienced jeweler, takes out jewelry from it. Thank you very much for a wonderful unforgettable tour!

The tour was fantastic as you got to see the whole old town in 3hrs. My tour guide was extremely knowledgeable about the history and culture of Tallinn and Estonia . The guide was more than happy to answer my questions and very helpful. I’d highly recommend this tour to anyone looking to do a walking tour in the old town.

Super relaxed tour of Tallinn. Volker responded to us individually and we had a great time. Would do this tour of the city with him again and again. Highly recommended, just great!

The walking tour was incredible. The guide was friendly and very informative. Great way to explore Tallinn and learn about it’s history.

Great tour with lots of cultural insights and a weave between the past and present. Anastasia was an excellent guide.