3 Perfect Days in Tallinn + Itinerary

Since we are expecting a baby, we wanted to take one last trip with just the two of us. We were torn between enjoying the pleasant weather of southern Europe’s coastal areas or embracing a winter getaway in the north. In the end, we chose Tallinn for its snowy charm, and we could not be happier with our decision.

About

Tallinn is over 800 years old, one of Europe’s best-preserved medieval cities, a UNESCO World Heritage site, and one of the most underrated and charming cities I have ever visited.

It is a city of contrasts, in the best possible way. Its medieval Old Town, with winding cobblestone streets, towering spires, and red-roofed buildings, feels like you are stepping into a fairytale. On the other hand, Tallinn is also one of the most technologically advanced cities, often called Europe’s digital capital, Tallinn is the birthplace of Skype and a global leader in e-governance. The city offers free public Wi-Fi almost everywhere, and locals handle everything from voting to prescriptions online. It is a place where medieval walls stand next to innovative startups.

Beyond the tech, Tallinn’s urban coastline is now a vibrant space for locals, with scenic promenades, wild swimming spots, and sandy beaches stretching from Kadriorg to Pirita. The food scene is equally dynamic, with MICHELIN-starred restaurants, seasonal menus, and cozy bakeries on every corner.

It is the kind of city you will want to return to because one weekend is never enough.

At least not for me.

Friday

Arrival and First Impressions

We arrived at Tallinn Airport just before lunch. The airport is not big, but it’s well-organized, clean, and easy to navigate. We caught a bus outside the terminal that took us directly to the city center. The tickets cost 2€/hour, making it an affordable and convenient option.

If you prefer a more comfortable ride, you can use the Bolt app to book a cab. Bolt offers reasonable prices, and you can save even more if you have a discount code.

We chose a hotel in the city center, which was the perfect location—close to everything. Tallinn is a very walkable city, and you can get anywhere within the historical center in under 10 minutes.

Luckily, we were able to check in early. We dropped off our luggage and, without wasting any time, set out to explore the city—and, most importantly, to find lunch!

Lunch

We were craving a good burger, so we decided to try VNLD Burger Vanalinn, which had excellent reviews on multiple platforms. We ordered a Classic Cheeseburger and a Double Major, and our taste buds were more than satisfied with the juicy, flavorful smashed burgers. I have to admit, I was a little envious of my husband enjoying a cold beer with his meal, it would have been the perfect pairing!

The Old town

After lunch, we set off to explore the snow-covered Old Town. Entering through Viru Gate, the grand medieval entrance, felt like stepping into a storybook. The streets, dusted with snow, seemed untouched by time, with every corner revealing a piece of Tallinn’s rich history.

Town Hall Square

We wandered into Town Hall Square, surrounded by pastel-colored merchant houses and dominated by the striking Tallinn Town Hall, built in the 1400s. It is open to visitors during specific periods throughout the year. From June 25 to August 31, during the festive season from December 1 to 30 except Christmas holidays and in early January, from the 2nd to the 5th. Its 64-meter tower stands proudly above the square, while a beautifully decorated Christmas tree in the center added a festive charm. Fun fact: Tallinn claims to have hosted the world’s first Christmas tree right here in 1441!

Raeapteek

Right across the Town hall is Raeapteek, Europe’s oldest, continuously operating pharmacy. Inside, you’ll find ancient remedies like powdered unicorn horns, dried hedgehogs, and even mummy juice (yes, really).

After strolling through the historic center, we decided to warm up at RUKIS Café with some sweet pastries to recharge our energy. Feeling refreshed, we continued exploring the Old Town, starting with a walk through St. Catherine’s Passage, one of Tallinn’s most famous and picturesque lanes.

Hellemann Tower

Next, we walked along the Hellemann Tower and Town Wall, where, for a small fee, you can climb up the medieval walls for beautiful views of the city and its snow-capped rooftops. We also visited the impressive St. Olaf’s Church before slowly making our way back to the hotel to rest and prepare for dinner.

Dinner

As the weather grew chillier in the evening, we added an extra thermal layer under our sweaters and headed to one of Tallinn’s most recommended restaurants – Rataskaevu 16. We had made a reservation a week in advance to be sure we would get a table, and it was well worth it.

The staff were incredibly friendly, and the food was delicious. If you have the chance to dine here, try the Braised Elk Roast—paired with celeriac, beetroot, carrot mustard, and blackcurrants, it was an amazing combination of flavors. We also indulged in some desserts, which were just as impressive. This restaurant truly lives up to its reputation. After that, we called it a night and headed back to the hotel. I was quite tired from not having slept well the night before (incredibly early flight), and with my growing belly, I wanted to rest and recharge so I’d have more energy for the next day.

Saturday

Morning

Ready for the next adventure, we wanted to fuel up with a good breakfast, so we headed to KOHVIK MUST Puudel. After a delicious start to the day, we made our way to the meeting point for our free guided tour with EstAdventures, a small tour company with a big heart and a wealth of knowledge.

Our guide, Marko, was incredibly friendly and deeply knowledgeable. As both a teacher and historian, he brought Tallinn’s history—and Estonia’s broader story—to life in a way that was engaging, insightful, and genuinely enjoyable. The tour covered the most important sights in the Lower Old Town and Toompea.

Toompea

Medieval Tallinn was once divided into two distinct sections: the Lower Town, a bustling hub of merchants and craftsmen, and Toompea Hill, the fortified stronghold of the nobility and political elite. While Toompea was historically off-limits to commoners, today you can wander its cobbled streets and take in stunning views of the city.

Toompea Castle

Toompea is the birthplace of Tallinn, where the Knights of the Sword built a fortress in 1229. This stronghold evolved into the Toompea Castle, which has housed Estonia’s rulers for centuries. Today, it’s the seat of the Estonian Parliament, with an elegant Baroque façade at the front and remnants of the original medieval castle tucked away behind.

Alexander Nevsky Cathedral

Dominating Toompea’s skyline is the striking Alexander Nevsky Cathedral, an ornate Orthodox church completed in 1900 during Estonia’s time under the Russian Empire. Built as a symbol of imperial power during the Russification period, the cathedral stands directly opposite Toompea Castle. We had to go inside to warm ourselves up during our guided tour before going to the panoramic views.

Viewing Platforms

For some of the best views of Tallinn, we headed to the Patkuli Viewing Platform, one of the city’s oldest vantage points. From here, you can see the Old Town’s medieval towers and stone walls stretching all the way to the port. Just a short walk away, the Kohtuotsa Viewing Platform on Toompea’s northern side offers views over the city’s red rooftops, Gothic spires, and the modern skyline beyond, with the Gulf of Finland glistening in the distance. My hands almost froze in the wind while I was trying to take a picture…

Kiek in de Kök

On our way back we made a stop at Kiek in de Kök Fortification Museum, a must-visit if you are a history lover. This 500-meter-long complex features four historic towers Kiek in de Kök (a “peep in the kitchen”), Maiden’s Tower, Tallitorn, and the Short Leg Gate Tower, along with the mysterious underground bastion passages. The museum’s exhibitions dive into medieval warfare, military strategies, and the evolution of Tallinn’s fortifications. Do not miss the Carved Stone Museum hidden within the tunnels. You can download the audio guide to your phone in advance for an immersive experience as you explore the labyrinth beneath the city. This free guided tour blended fascinating historical facts with modern-day context. It was a wonderful way to get to know the city on a deeper level. I cannot recommend them enough.

Telliskivi Creative City

After all that history, it was time to experience Tallinn’s modern, creative side at Telliskivi Creative City and grab some lunch at F-Hoone, a local favorite. I had the dumplings in mushroom sauce, and oh my, were they delicious!

Telliskivi Creative City, a former industrial complex, has been transformed into a hip, artsy neighborhood filled with street art, indie shops, and cozy cafés. We could have spent hours here, wandering through unique boutiques and visiting Fotografiska, a world-class photography museum with a rooftop café offering fantastic city views. The area also hosts a theater and a contemporary dance platform, adding to its vibrant cultural vibe.

With over 800 cultural events held throughout the year, Telliskivi is a dynamic space that’s always buzzing with creativity. I can only imagine how lively it must be in the summer—I am pretty sure this would be my favorite part of the city during that season. And of course, the incredible street art adds the perfect finishing touch to its urban charm. How cool are they?

Dinner and Fun

In the evening, we had a reservation at MOON, an Eastern European restaurant with a modern twist that is featured in the Michelin Guide. Despite its accolades, the place had a down-to-earth vibe, with warm, welcoming staff and incredible food. I cannot praise the dessert enough—warm cottage cheese Syrniki served with vanilla ice cream and salted caramel. Absolute heaven!

After dinner, we took a chilly evening stroll through the Kalamaja district, known for its charming wooden houses, on our way to Heldeke, an underground bar where we had tickets for a stand-up comedy show. The show was in English, and we had a wonderful time laughing the night away. My husband also enjoyed trying some unique craft beers on tap.

Heldeke is not just about comedy, they regularly host concerts, shows, magic acts, and even offer sauna sessions and pizza if you’re up for something different. It was definitely worth a visit and a perfect way to end the evening!

Sunday

Morning

Sunday was all about taking it slow, something Tallinn does incredibly well, as the daylight wasn’t present until 9:00 am.

We had a brunch at Värav Coffee, a very little but charming cafe in the middle of a snow-covered parking lot. After that I had a craving for something sweet, so we made a stop at La Boulangerie close to the modern Rotermann district, which is filled with modern architecture. (I would love to take an Airbnb in summer there), and my taste buds were jumping for joy when I saw all the displayed pastries from which I could choose. (Pregnancy can do that to you!)

The Seaplane Harbour

Next, we took a bus to the Seaplane Harbor Maritime Museum, one of the most impressive museums I have ever seen. Set inside a massive, hangar-like space, it displays Estonia’s seafaring history in a way that is interactive, immersive, and just plain cool. Even if you are not a museum person, this one is special as you can try some interactive games and several gadgets.

The highlight? Climbing inside an actual 1930s submarine—tight quarters, periscopes, and all. This museum is well worth a couple of hours. It also has an exterior part, where you can climb up on some ships or even take a hot sauna and jump into the ice-cold seawater after! My Italian husband was a bit shocked, but I totally would have gone for it if I could.

Dinner

For dinner, we booked a table at FARM, a modern Estonian restaurant located near the Viru Gates. They offer a fusion of traditional and contemporary cooking techniques, using the finest local ingredients complemented by high-quality imports from around the world, all prepared in an open kitchen.

The food was excellent, and we would definitely go back. However, the beverage prices felt a bit steep – €7 for a 0.75L bottle of natural water. Next time, I will opt for tap water instead!

Monday

Helsinki Trip

For our final day, we decided to take a ferry trip to Helsinki. We booked our tickets with Tallink Silja as it had the best timetable and prices for us. The journey was only two hours long, and we opted for the buffet breakfast on board, which turned out to be a smart choice. You can choose a business class ticket too, where you have access to another buffet with unlimited drinks. As we arrived, the sun was just starting to rise, casting a beautiful light over the harbor.

We had some time before our free walking tour, so we started to explore on our own. The tour was incredibly helpful—our guide shared fascinating insights about Helsinki’s history, pointed out the architectural similarities within the city, and led us through interesting streets and landmarks with naked women and unicorns!

We visited the impressive Oodi Library, a stunning example of modern architecture, and later headed to the Old Market Hall for a late lunch, where we enjoyed tasty local flavors. We also passed by the several public saunas along the waterfront, as the sauna is an essential part of Helsinki’s culture.

In the evening, we took the ferry back to Tallinn, feeling exhausted after a long, cold day, though the locals mentioned it was unusually warm for the season!

On our way home, we grabbed a quick sandwich, eager to get some well-deserved rest, but we were happy and satisfied with our little adventure.

For a more detailed post about Helsinki, read One Day in Helsinki post.

That was our last day in Tallinn, as we caught our flight back the next morning. I honestly can’t praise this city enough, its charm, modernity, and vibrant atmosphere left a lasting impression. I would love to return someday in the summer to experience it from a whole new perspective.