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family in front of old buildings

Step Back in Time for a Day in Old Town TALLINN, ESTONIA

Tallinn’s Old Town is one of the best preserved medieval cities in Europe, making it easy to imagine that you are going hundreds of years back in time when you walk it’s cobbled streets.

September 13, 2020 //  by Kim//  Leave a Comment

My husband lived in Estonia for 2 years and speaks Estonian so the country has a special place in our hearts. We love the people and the visible history in the buildings, streets, and landscape. Nowhere is this more pronounced that in Old Town Tallinn.

family in front of old building

We’ve visited as a couple and later with our two oldest children and their grandparents. Here’s how we recommend spending a day in Old Town.

Explore the Streets: On Foot or Wheels

Old Town is full of quaint cobbled streets and little shops for browsing or picking up souvenirs. Check out beautiful wool socks and sweaters and Baltic amber trinkets as you walk around the town.

woman standing on street
man painting pictures by wall
four people standing in street of old town

You won’t want to miss the beautiful views from the Kohtuotsa Viewing Platform at the top of Toompea Hill.

parents and kids standing at lookout over city
Red tile rooftops

If you are feeling extra adventurous, consider renting Segways. We had so much fun motoring through the streets and were able to more easily explore nooks and crannies off the beaten path.

boy riding a Segway on cobble street
woman riding Segway on cobblestone road

Lunch at 111 Draakon

This place at the center of Old Town is full of character and the food is budget-friendly and tasty. We recommend that you try a “decent bowl of elk soup” and the pasties, and you can spear a fresh pickle right from the barrel to go along with your lunch!

The staff does a great job of creating the atmosphere of a gruff old pub. Be ready (and prepare your kids so they aren’t upset by it!) for some scolding and gruff talk, it’s all part of their act.

man, woman, and child in front of arched door
man drinking soup from a bowl
boy spearing a pickle from a barrel

Dinner at Olde Hansa: Authentic Experience and Food

Give yourself time for a leisurely dinner at Olde Hansa to get a real feel of Estonian life hundreds of years ago. This is an experience you won’t want to miss!

The restaurant is candle-lit and everything inside feels right out of medieval times. The food is even made from centuries-old recipes. We tried the game sausages with sides of onion jam, barley, lentils, and more and the flavors were really unique, warm, and hearty.

woman in front of old buildings
restaurant menu
candle-lit restaurant tables
sausages, lentils, barley on a plate

Getting to Tallinn

By Air

The Tallinn Airport is really unique. There are lots of comfortable places to wait and good places for kids to play. This video from YouTube is a few years old, but it gives you a good idea of the character and charm of the Tallinn Airport!

By Sea

On our second trip, we found much cheaper plane tickets into Helsinki, Finland, so we flew there then took a ferry to Tallinn.

father and kids standing on ferry at night

Tallinn is a popular stop with cruise ships and Old Town is just a short walk from the cruise port in Tallinn.

Where to Stay in Tallinn if you are Lucky Enough to Stay More than a Day

On our first trip as a couple we stayed at the Radisson Blu Olumpia, a beautiful hotel with all the modern amenities just a 15 minute walk from Old Town. The breakfast buffet there is delicious and the rooms comfortable. Here’s the view of downtown Tallinn from our room:

view of city buildings from above

On our second trip we rented an apartment right in Old Town on Booking.com. The location was perfect and we loved the full kitchen for cooking some meals at home and the extra space to comfortably accommodate our group.

boy standing in courtyard

Extras

Here are some of the foods that my husband remembered fondly from his time in Estonia: Hiirte Juust cheese, sausages, dark rye bread, candies, and bagged sour cream! We love going to grocery stores in foreign countries to save money and get a taste of local foods!

food on a park bench
plate of food

I always think it’s fun to be able to greet and thank locals in their own language. Try these words out in Tallinn and you’ll be rewarded with smiles from the friendly Estonians!

Hello: tere (teh-reh)

Thank you: aitäh (eye-tuh)


We love exploring old cities. Old Town Gdansk; Orvieto, Italy; and the Old City of Jerusalem have been some of our other favorites. What other old cities do you love?

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Category: International Travel, Trip Reports

About Kim

I am a wife and mom of three kids. I am also a traveler and a writer. Our family has been traveling together since my husband and I were newlyweds. On our first trip to Hawaii when our oldest daughter was 6 months old we tried to soak it all in because we thought it would be a once-in-a-lifetime experience. But with some learning, ingenuity, and flexibility we have made family travel part of our lifestyle.

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