Tallinn's Attractions: A Journey Through Time

Judy Hebron

Updated: 26 May 2026 ·

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Tallinn's Attractions: A Journey Through Time

Tallinn, the charming little capital of Estonia, is known for two main things: its impressive medieval atmosphere and its pioneering role in digitalization. Our blogger Matthias takes you on a journey through Tallinn's attractions, where you will experience a journey through time while embracing the future!

It's late. The airport is not as crowded as it was a few hours ago. As I sit on the plane, a feeling of excitement and curiosity overcomes me. The last time I was in Tallinn was nine years ago. The stay was short, just six hours before the ferry back to Stockholm. But even that amount of time was enough to get a little impression. Back then, I was already sure that I would return to immerse myself in this extraordinary city in the Baltics.

As I try to take a taxi to the hotel, a girl with her mother approaches me: 'Are you heading to the city? Let's share a cab!' Sure! The mother grew up in Tallinn before moving to Germany. Now she wants to show her daughter her hometown.

Estonia: A Pioneer in Digitalization

The trip was made possible by the kind support of Fly Nordica.
photo by www.travellers-insight.com

And to be honest, a lot has happened in her homeland over the last fifteen years. More and more young people from all over Europe are drawn to Estonia's digital paradise. Citizen and data protection are at the forefront of digitalization. An Estonian has a card for everything: insurance card, driver's license, identity card, library card, and supermarket loyalty card. Every citizen has a digital signature, and voting can also be done digitally, since 2005. This saves over 800 years of administrative work time every year. This article from Süddeutsche Zeitung describes what Estonia has achieved in terms of digitalization as the only country in Europe so far.

Tallinn's Attractions: Enchanting Old Town

A street leads through the large archway of the old city wall of Estonia's capital Tallinn, with three watchtowers reminiscent of times past.
On a tour of Tallinn's attractions. Here are the old city walls. photo by www.travellers-insight.com
With a view of the city of Tallinn, the phrase: 'The time we had.' is written on an orange wall.
'The Times we had.' - Words that evoke personal memories for everyone. photo by www.travellers-insight.com

Despite the impressive digital progress, the country has lost none of its original charm. The next morning, I set out to explore Tallinn's attractions. First, I head to the old town, the most well-known and beautiful part of the city.

The city walls with their broad towers surround the old town, and the streets still consist of the original cobblestone. You feel like you're on a journey back to the Middle Ages. Now, the environment feels familiar again, as that was the thought I had during my first visit.

I discovered a great viewpoint on Instagram, and now it's time to find it. Equipped with the VisitTallinn app, I think I know where this place might be. And behold: discovering the Dome Hill was easier than I thought. It's also helpful that Tallinn's attractions can be wonderfully explored on foot. From up here, you have a breathtaking view of the city. To the right stretches Tallinn's skyline, and before me lies the beautiful old town with its lively streets and roofs shimmering in every imaginable shade of red and orange. At the moment, these are mostly covered with snow, which is also very pretty. To the left, you gaze upon the city wall with its broad towers, and behind it, you can even see the harbor.

Restaurants in Tallinn: Culinary Journey to the Middle Ages

A woman in medieval clothing sells macaroon and almond products at her market stall in Tallinn.
You can find medieval vendors everywhere. photo by www.travellers-insight.com
At a medieval-style market in Tallinn, caramel candies are arranged on an old wooden table in a basket for sale.
And everywhere you can taste the delicious caramel candies... photo by www.travellers-insight.com
In front of the medieval facade of the Olde Hansa restaurant in Tallinn stands a medieval market stall.
The Olde Hansa restaurant - Dining like in the Middle Ages. photo by www.travellers-insight.com
At Tallinn's restaurant F-hoone, a dish with venison fillet is served on a clay plate by candlelight and a clay mug.
The Mayor's venison fillet - the best meal on the menu. photo by www.travellers-insight.com
The window display of Café Kehrwieder in Tallinn shows truffle chocolate for sale, with a small seating area in sheepskins by the entrance.
Café Kehrwieder's little truffle shop features the best truffles in town. photo by www.travellers-insight.com
In Tallinn's Café Kehrwieder, various variations of truffle pralines are visible in the display.
Various homemade truffles in all shapes and flavors. photo by www.travellers-insight.com

In Tallinn's old town, you repeatedly encounter women dressed in medieval clothing selling delicious caramel candies. They come in many different flavors, and tasting is highly encouraged.

Next to one of these stalls, I notice a restaurant, Olde Hansa. Is that not the restaurant that the Estonian recommended to me the night before in the taxi? It's lunchtime, and I'm hungry since I opted for sleeping in rather than having breakfast at the hotel. What I experience here is beyond my expectations: All food and drink are prepared as they were 600 years ago. Even light bulbs have been replaced by candlelight, and meals are served at rustic wooden tables. Ivar brings me the menu, which he has translated into three different languages himself. I let him recommend me a game dish - venison, accompanied by millet porridge and berries - and I'm thrilled by how good it tastes and how natural and wholesome the food was back then. For dessert, I have rose pudding with rose petals, along with a shot of liquor that is surprisingly strong. Who drinks such things? People from back then, says Ivar.

Afterward, I wander through the rest of the old town. I'm on the lookout for any corners I recognize from the past. Oh yes, the Peace Square with its massive cross. It's getting dark, and it seems I've lost my way. Due to all the small, winding alleys, this can happen in Tallinn. Suddenly, I find myself in front of a compact, unassuming shop. Curious, I go inside. Here, they sell truffles in every shape, color, and flavor. The quaint shop belongs to the neighboring Café Kehrwieder. I highly recommend trying a few truffles here.

Kalamaja District: Trendy Neighborhood of Tallinn

This trip was made possible by the kind support of Visit Tallinn.
This trip was made possible by the kind support of Visit Tallinn. photo by www.travellers-insight.com
This trip was made possible by the kind support of Unique Hotels.
This trip was made possible by the kind support of Unique Hotels. photo by www.travellers-insight.com
The view of the streets of Tallinn's Kalamaja district shows colorful wooden houses with snow on the sidewalk.
The colorful wooden houses in Kalamaja remind one of Scandinavia. photo by www.travellers-insight.com
In the Kalamaja district of Tallinn, a colorful dragon is seen as graffiti on a high wall protrusion.
Street art in Kalamaja. photo by www.travellers-insight.com
In Tallinn's restaurant F-hoone, burgers with fries are served at a wooden table, with a wall of colorful posters in the background.
Food, drink, and people-watching at restaurant F-hoone. photo by www.travellers-insight.com

Since I not only enjoy exploring places slowly and mindfully but also have a penchant for off-the-beaten-path destinations, I always try to find the less touristy side of a city. Here in Tallinn, that place is Kalamaja. This neighborhood was once a fishing district. While not many of the fishermen remain, the beautiful wooden houses where they lived are still there, shaping the image of this area.

Directly behind the train station, you can find not only a lot of street art but also more and more trendy restaurants as well as creative modern art. Kalamaja has developed into a hip neighborhood.

The cafés with their quirky designs are well-frequented. They are meeting spots for many young and some older visitors. One thing stands out to me: there is a lot of laughter; the people here seem very content. Unlike many trendy cafés or neighborhoods in other countries, people in Kalamaja dress quite normally and unobtrusively, which I find very appealing.

It's lunchtime again, and I set out in search of something edible. In a small side street, I notice a signpost. Although I don't understand what it says, my curiosity is piqued. A few steps further reveals an impressive painting on a large house wall. Next to it, more wonderful paintings emerge, along with a kind of sculpture hanging from the small tunnel.

I take a few photos and then discover a restaurant just around the corner. The F-hoone looks very inviting, and I decide to stay.

Excursion to the Surroundings: Attractions Kadriorg and Pirita

Tallinn's public transport will take you from point A to point B in no time. The best part is: Anyone who lives in Tallinn or is registered there can use it for free. On my last day, I planned an excursion to the Song Festival Grounds in the Kadriorg district and a visit to the suburb of Pirita. Kadriorg is a vast park located thirty minutes from Tallinn's center. In winter, you can go sledding here and enjoy great walks. A little further lies Pirita, located right on the Baltic Sea beach, boasting its idyllic harbor and a beautiful view of Tallinn. Although that sounds absolutely enticing, I have to regretfully cancel the excursion last minute due to heavy snowfall. It's a shame, but also a good reason to visit Tallinn again soon. Since the Estonian capital and surroundings offer so much more to discover, it surely won't be long until I return.

Image Credits:

Featured image: © Ilya Orehov on Unsplash

all other images: Matthias Derhake