If Tallinn’s colorful town square and twinkling Christmas market aren’t yet on your radar, I’m insisting that they need to be. It’s one of the coolest (pun intended) places I’ve ever been, and evokes all of the childhood storybook dreams of yore.
I’ve read that Old Town Tallinn lacks texture – that the town seems plucked out of Disneyland and manufactured for tourists. Personally, I couldn’t have found that further from the truth. Once you poke around a bit, you’ll find that beyond its obvious charm and picturesque vistas, Tallinn holds a rich and uniquely interesting history, deeply nuanced people, and an under-rated cultural scene.
This icy-cold week in Tallinn is one that we bring up, reminisce over, and laugh about often. Like, on a weekly basis. I know. Read on for all of my Tallinn recommendations (especially if you’re traveling in the winter).
Where to Stay in Old Town Tallinn
In terms of accommodations, I’m mostly an Airbnb gal. Although I enjoy indulging in a luxe hotel room every once in a blue moon, renting a short-term apartment is usually more practical.
We stayed in two different Airbnbs in Tallinn, and I loved both! This pristine apartment was perfectly situated, only a few streets away from the main square in Old Town. We called it home for one night before leaving for a roadtrip to Riga; upon our return from Riga, we chose to hole up in the Kalamaja neighborhood for the rest of our stay. (This was our Airbnb in Kalamaja.)
Um, sign me right up for a romantic getaway in this darling studio right in the middle of Old Town.
What a gorgeous, light-filled space with a prime location, for a great price too!
Traveling with a bigger group? This colorful apartment has enough space for eight people. Plus, it has a sauna!!! ALL the cozy.
If you’re only in Tallinn for a day or two, I recommend finding accommodations in Old Town to really maximize your time. In the winter, it’s also such a clutch move when you can quickly run back to the apartment to grab some extra layers.
For a longer trip in town, I urge you to consider staying in Kalamaja to get acquainted with local culture.
What To Do in Tallinn in the Winter
Cassandra and I delighted in the empty streets, being extra careful not to slip. We pelted snowballs at each other and admired the medieval towers capped in white. Our hoods were weighed down with matted snow. I stuck my tongue out, hoping to catch falling snowflakes.
It was like being a kid again.
For us, no activity could top playing in the snow and ducking into cozy coffee shops afterwards. But here are a few that came close, and that you might enjoy on your own winter trip to Tallinn.
Tallinn Christmas Market
There are European Christmas markets, and then there’s the Tallinn Christmas market. You absolutely must spend some time here if you’re visiting in the winter. There’s so much to take in.
In the center of Raekoja Plats, the Town Square, a towering fir brightens up gray skies. (Here’s a festive fun fact for you. Tallinn was home to the very first Christmas tree in history, back in 1441.) Mulled wine simmers enticingly just yards away. Locals, ensconced in charming wooden huts, quietly sell wool hats, gloves, and painted ornaments.
Cassandra and I were absolutely delighted by the scene. Imagine our glee when it started snowing, becoming an actual picture-perfect winter wonderland. With a goblet of mulled wine in each hand, we twirled around happily under the Christmas tree.
Check out the most up-to-date news and program schedules for the Tallinn Christmas Market, as well as other Christmas markets in Estonia, here.
Tallinn Free Walking Tour
I didn’t know a thing about Estonian history before joining this excellent tour on our first full day in Tallinn.
Conducted by passionate local youths, it’s the best way to see and learn about all of the famous landmarks. Our guide led us through the historical quarters of lower Old Town, around the government buildings of upper Toompea, and to the vista points that overlook a sea of red rooftops.
The most meaningful part of this tour was its brief lesson on Estonian history and its various occupations (Vikings! Danes! Russia! Nazis! Soviets again!), as well as its illustration of what it’s like to live in Estonia now. Frankly, I’d move there in a heartbeat. Free public transportation, universal health care, and everything is digitalized and so technologically advanced.
I left the tour feeling so much more in tune with the city that I was standing in.
Make sure to tip your guide! Find details on meeting time and place here.
Visit Kalamaja
I wrote a whole blog post on the best things to do and eat in Kalamaja, the funky hipster district nestled up right next to Old Town.
It’s definitely worthwhile to pop on over across the train tracks to see the wooden fishing houses, shop at Telliskivi Creative City, and grab a bite to eat at one of Kalamaja’s amazing cafes or restaurants.
Staying in Tallinn for a longer stretch? Consider renting an Airbnb in Kalamaja for a couple of nights to experience a different side of the city. That’s what we ended up doing. I feel we left with a much more nuanced understanding of Tallinn than we would’ve otherwise.
See Tallinn From Above
Gosh, Tallinn is picturesque. While I didn’t stumble across a single bad angle, I think the most breathtaking views of all are those from above. In fact, it was a capture of red rooftops at dusk that stopped my thumb mid-scroll, tempting me to start looking into flights to Estonia.
Here are a few of Tallinn’s most striking viewing platforms and photo ops:
Kohtuotsa Viewing Platform: This is where you’ll find the famous “The Times we had” wall (it’s written in a different font as of 2019). Bonus points if you can catch Steven the Seagull on your visit! We came to this viewing platform with the free walking tour first and admired the terracotta rooftops. Once it started snowing, we raced back here again on a hunch that the town blanketed in snow would be a sight we wouldn’t soon forget. And I mean… the pictures speak for themselves.
Patkuli Viewing Platform: another gorgeous vantage point, you’ll also be treated to a sweeping panorama of Lower Toompea below.
St. Olaf’s Church: greet incredible views of Tallinn from up high after climbing to the top of St. Olaf’s Church, one of the oldest and tallest medieval buildings in Tallinn. There’s a small fee and 200+ steps, but do it for the ‘gram!
Visit the Hotel Viru KGB Museum
OK, confession. The KGB Museum was at the top of our list of things to do in Tallinn, which is a big deal because we are not Museum People. After our morning walking tour and some light sight-seeing, we started to make our way to the museum.
Then, it started snowing. At the same time, both of us realized that our Tallinn off-line Google Maps didn’t successfully download. After trying to follow a few street signs to no avail, we finally declared it a failed attempt and accepted that perhaps museums just weren’t meant for us to explore.
In all seriousness, the KGB museum looks fascinating. Go, and report back on all the stories that I missed out on.
Go On a Day Trip
One of our biggest takeaways was that there is so much to see in Estonia outside of Tallinn. While we managed to quickly explore a couple of small towns en route to Riga (Viljandi was our favorite), there are so many other excursions that I’d love to go on too:
- Go on a picnic by the frozen Jägala waterfall
- Take the ferry to Helsinki and back (note that this isn’t a regular ferry, it’s a cool ferry – karaoke, alcohol, and fun times galore)
- Enjoy Estonia’s natural beauty at Lahemaa National Park
- Visit the cities of Tartu and Viljandi for the day
Best Food & Drink in Old Town Tallinn
Tallinn Christmas Market Food Stalls
Imagine this. The wind is brisk and unforgiving, hinting at snow in the not-too-distant future. You are bundled up in thermals and a parka and a scarf and earmuffs, and resemble a jolly Michelin Man. Your dinner reservation is in an hour, and you really shouldn’t be eating before that. You decide to just take a gander around the market and perhaps purchase a few ornaments for mom…
and then it hits you. The ‘crack, crack, crack’ of sausages roasting away on a hot pan; glistening piles of gloriously red-purple cabbage; buttery potatoes in bed with steamy stews. And the dumplings! Pan-fried golden and perfectly plump, they burn your tongue, but OH is it so worth it. With just a graze of salt and a tiny pillow of sour cream on top, it’s the most delicious explosion of flavor in one bite.
The choice is obvious. You’re going to give in to a pre-dinner dinner, and you’re going to need a generous portion of Vana Tallinn-flavored Glogi (mulled wine) to wash it all down. Give in, love. Vacation calories don’t count.
Cafe Maiasmokk
Cafe Maiasmokk came highly praised and also happens to be the oldest cafe in the city of Tallinn.
We found ourselves a table by the window, pulled out our journals, and quietly enjoyed a pavlova and cappuccinos in the warmth. The cafe does get busy as it’s lauded by many a travel guide and tour group. But if you tuck yourself away at a corner table, you’ll experience equal bouts of quiet and excellent people-watching.
Kompressor
Based on our tour guide’s recommendation, we feasted on crepe-style pancakes at Kompressor, which is a local favorite.
Its aesthetic is reminiscent of my freshman dorm’s dining hall, but its pancakes are hearty, filling, and perfect for a cold night.
Rataskaevu 16
We heard from many, locals and travelers alike, that this is the best restaurant in Old Town Tallinn. Sadly, we couldn’t snag last minute reservations. Their entire menu looks so tasty!
Wine Not
The setting of what became my favorite travel memory of all time. After a jet-lag induced nap after dinner, we forced ourselves out of bed, into parkas, and onto the streets of Old Town, with the goal of finding a pub for a quick nightcap.
There was no pub in sight, but a tiny storefront with the name “Wine Not?” down a silent street beckoned to us.
The first glass of wine was pleasant. We enjoyed a chat with the owner, a young Portuguese fellow who had moved to Tallinn for love.
Cassandra and I chatted quietly to each other. China soon became a topic of conversation. The woman behind me tapped my shoulder and said that she couldn’t help but interrupt… She heard us talking about China. She actually just returned from a business trip there…
Soon, we were talking about Tallinn and how we had found our way here over Thanksgiving,
and then we moved onto our great love of traveling through the Balkans,
followed by the man telling us all about Mongolia and his travels,
then their dog Oxford, work, and society, and Estonian culture…
The owner soon pulled up a chair to join the conversation, and Cassandra and I swung our chairs around too. Before long, two younger guys filed in, declaring, it looked like such a party in here! It turned out that they were diplomats, and so then we were interested in their take on Estonia.
Then, a Finnish gentleman walked in, followed by the man who lived upstairs. We engaged in spirited discussions about politics and ethics and history (tears were shed at one point), and traveling and restaurants, and Estonia, America and everywhere in between. Our wine glasses were never empty, not once.
Cassandra and I made eye contact and kind of shook our heads in disbelief. One tiny wine bar, seven glasses of wine deep, six hours, eleven strangers, hearing their stories, sharing ours. Our Finnish friend downed one last glass of wine and stood to leave. “I was feeling very blue tonight because I found out my mother was diagnosed with melanoma… so thank goodness for passionate people and great conversations!” It felt absurdly poignant and serendipitous.
By the time we finally left, it was nearly 3 in the morning. We were halfway home before realizing that we’d taken a wrong turn somewhere and were very, very lost. And so there we were, blindly walking around Old Town in circles, not a single other soul in sight. At one point we found ourselves back at the wine shop only to find the doors locked, the lights off. It was almost as if we had dreamed it all up. And if it all didn’t seem like a movie already, we were soon caught in a torrential blizzard. When we finally made it back to our apartment, our fingers were frozen solid, and our sweaters were soaked through, but I don’t think we could’ve been more grateful for such an evening.
Alexander Chef’s Table
It looks like Alexander Chef’s Table is only available on Muhu Island for the 2019-2020 season. Keep an eye on their website to see if it returns to Old Town Tallinn next year!
Alexander Chef’s Table was such a special dining experience. You’re invited into the Tallinn home of the head chef at Estonia’s top restaurant (Michelin-starred Alexander Restaurant, located on Muhu Island) for a multi-course tasting menu. At the time, Chef Matthias Diether hosted us for an unforgettable evening. Although it looks like there is a different chef at the helm now, I have no doubt that the experience would still be fantastic.
With only 16 guests each evening, it’s an intimate affair. You are all seated at the same table and served the same courses. There was one young Estonian couple seated next to us. The rest of our group all belonged to the same party… a literal birthday party, that is. We had an absolute hoot being honorary guests at a very dignified Estonian gentleman’s birthday party, standing every few courses to toast to him or sing to him.
The food was unforgettable, the wine glasses were never empty. Best of all – the atmosphere was so fun, interactive, and positive. We were encouraged to walk up to the kitchen area and sample spoonfuls of sauce, and were invited to a secret corner to help unveil the cotton candy machine that would provide us a whimsical dessert.
After dinner, the two of us remained behind to chat with the chef, sommelier, and kitchen staff over cappuccinos. They wrote down Tallinn recommendations for us, told us their own stories, and sent us home after midnight still giggling.
Tallinn is growing ever-so-steadily as a top European winter destination. It has so much to offer: delightful winter treats, breathtaking scenery, and a charming, storybook feel. Because it’s still an emerging hot spot, there are also authentic experiences hiding around every corner, waiting for you to be the first to discover them.
I have a huge soft spot for Tallinn after our wonder-filled week there. I hope you leave with that same sense of magic too.
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