Winter travels are very underestimated, and in most of the cases they are limited by flying to a tropical island with a whole-year-round summer, or spending a week in a ski resort. We are still convinced though, that city-breaks or road-trips in winter can be as much fun, as during any other season. If not more, as the off-season tourism has much more advantages than it might seem at the first glance.

This time we want to bring you back to Tallinn.

Two years we spent in Estonia during our first expatriation. We know this country as well as it could possibly get, better actually than our own ones. Tallinn was our regular destination, where we went for shopping, concerts or to the airport – to catch a flight wherever we were going. So yes, we feel pretty much like locals. Difficult to describe how happy I was to be back two years later and to discover that all the reasons why we loved Tallinn were still there. Even more, numerous reconstruction works were finally over, so Estonian capital appeared to be as beautiful as it was kept in our memories despite the unfortunate weather conditions.

All the same reasons as why visit any place off-season: less tourists, lower prices, less queues. Apart from that, Estonia is one of those countries where you can enjoy the true winter, with the fluffy snow, low temperatures and a completely frozen sea at some places. Even if the fairy-tale winter occurs in Tallinn rarer than it used to be, the Old Town under the thin layer of snow, as if covered with sugar, looks fantastic. And of course, the Christmas Market, if you visit in December. Hot Wine with a touch of traditional liquor – Vana Tallinn. That is what makes Tallinn look like a magic town in a ball – you shake twice, and it slowly drowns under the snow.

Initially I would say just a weekend, but thinking over the places to see, I think that three days would be a perfect minimum. The one huge drawback of the winter city breaks are the short days, which doesn’t allow enough of time to spend outdoors, so plan your day accordingly, leaving the “indoor activities” for the darkest of times. :D

It is more than possible to have no luck with the weather at all. Due to its position near the sea, Tallinn in winter is very windy and the chill gets straight to the bones, so make sure you dress appropriately. I won’t get tired of saying, that good clothes can solve any issue.

We’ll suggest you the itinerary, with somewhat crazy transport solution, but it’s up to you whether you want to try it on or not :) In the worst-case scenario, you can always keep it to somewhat better weather conditions.

The Old Town of Tallinn is the best-preserved medieval capital of Baltic, it has so many secret streets and yards, cute little shops or cafés, so even if the town is small, it is still difficult to see it all without knowing where to go exactly. No matter in what order you get to see the best spots of the Old Town, as they are all very close to each other, but let’s start straight with the heart:

Tallinn Town Hall

Town Hall and the Town Hall Square are inevitable stops while visiting Tallinn. The Gothic building of the Town Hall, with the tower (opened for visitors in summer) and the iconic Old Tomas on its top might look somewhat clumsy from a short distance, but from the streets running from the square, it looks much more impressive. It’s here that happens the annual Christmas Market. This beautiful tradition originates in Germany, but it’s one of few that I’m happy to see globalised, and there is hardly any place as ideally suited for the Christmas Market as Tallinn Town Hall Square. Normally, it starts in the last days of November and lasts up to the first week of January, so try not to miss it!

While you are still here, take several minutes to visit the Town Hall Pharmacy – the oldest continuously working Pharmacy in Europe, but along with the mummified hedgehogs, one can also get a regular Ibuprofen.

Town Walls

Tallinn is a fortified town, with almost 2 kilometres of city walls, bastions, gates and twenty towers preserved in an excellent state. The best in Europe, to be more precise. The walls can be visited, but you can also see them from inside the town as well as from outside – check out the Patkulki viewing platform. Many of the towers were turned into museums, but if to choose one, we would highly recommend the Kiek in de Kok and Bastion Passages Museum – an interactive and very well thought guided tour, we genuinely enjoyed it without being crazy about guided tours in general.

Toompea Castle

Toompea Castle was and stays a central point of the Estonian government. The castle includes the most iconic tower of the whole country – Tall Hermann with a compulsory Estonian flag on the top. Listed in the UNESCO World Heritage, it’s the best seen from the outside, as from the inside you can only see the actual government building. You will surely notice the Alexander Nevsky Cathedral – an “ordinary” Orthodox Church, but it is extraordinary in the cityscape of the Medieval Tallinn.

St Catherine’s Passage & Masters Courtyard

I do hope you will be lucky enough to see the St Catherine’s Passage under the snow, a narrow lane with lots of authentic craft shops close to the huge stall with knitted clothes, where you can get that woollen sweater with the reindeer. Evening, snow and yellow glow of lamps – it’s one of the most beautiful views of Tallinn. A bit similar place would be the Masters Courtyard – a truly hidden gem, which, I must confess, is far less cosy in winter in comparison to the summertime when the cafés put the tables out. Still, it’s the best place to get some hand-made souvenirs or clothes.

Viewing Platforms

Tallinn has three famous viewing platforms and each of them deserves a climb! Though my personal favorite (as well as the one of everyone else) is Kohtuosa Viewing Platform, which overlooks the Old Town with the Modern Town behind. Beautiful.

If you had enough of the Old Town of Tallinn, which is an unlikely thing by the way, there are many other things to see around. For this purpose, I decided to take care of my transport in somewhat extravagant way and rented… an electric bike. Yes, in winter. Going ahead, it was an excellent idea, which helped me to avoid all public transport adventures and see much more in one single day without sweating, getting a cold and dying. Only advantages! If there are any other bicycle junkies as we are, just make sure you inquire about the e-bikes availability in advance. Due to the off-season period, they might be just stored away, but with CityBike I was very lucky.

First I went to Pirita Tee – a long promenade along the city, from which you can see the huge ferries leaving towards Finland, Sweden or Russia. Magic. A compulsory stop at the Tallinn Song Festival Grounds – empty and somewhat sinister in winter, I remember it full of live and joyful in summer, when the Estonian Song Festival takes place.

Kadriorg Palace

We cherish this place particularly, as it was here that we had our wedding photoshoot (made by ourselves!). Kadriorg Palace slightly reminds a reduced version of the Peterhof Palace near Saint Petersburg, and it’s not wonder given that it was also built by Peter the Great. Today the palace hosts a permanent exhibition of the Estonian Art. By the way, the streets around Kadriorg are also worth a stop – wooden houses in a traditional style, it’s difficult to believe that it’s not just an open-air museum!

Rotermanni kvartal – a relatively new hipster area where you can get some revised fusion meal and a good cup of coffee. As it is situated close to the port, I cycled to see the old Concert Hall – a true piece of a Soviet decadence. Now it is a perfect place for the street art, but I genuinely liked this half-abandoned spot.

Kalamaja – a cute district with wooden houses similar to those around Kadriorg. These days they follow the road of gentrification, becoming more and more popular as a place to live, but it remains quiet and very authentic. For my lunch pause I chose the Balti Jaama Turg – a restored market with the prices somewhat higher than the average, but a great place for warming up, surfing on the WiFi with a coffee. It’s winter after all, isn’t it?

One thing you should definitely not miss in the area is Telliskivi Loomelinnak, which means Telliskivi Creative City. A true place of hipsters, creativity, art and youth. Rotermanni kvartal multiplied by ten. I went there much later though, when it was too dark for photos, but trust me – you must not pass by this former industrial zone with a second life!

If you happen to be a completely cold-resistant specimen with an extra free day, why not going even further?

Soviet Tallinn. Whether one wants it or not, but history remains history, and the history of Soviet Estonia is no less interesting, than its Medieval or Modern period. Probably, it’s just my twisted fetish. Anyway, you don’t have to go far to see the examples of Soviet architecture – it starts directly out of the Old Town, but as I had a perfect transport, I cycled till the end of Kopli street. It’s not something I would suggest you doing, but if you are fond of an “alternative” tourism – why not?

Estonian Open Air Museum. If you are lucky to see snow, it will be a very beautiful stay. If not, the visit might be not that enjoyable after all. It’s Estonian traditional architecture we came to explore after all! By the way, a good reward for the efforts and the freezing would be a visit to the SPA, which also happens to be in the same area. Estonian mud is said to be very beneficial for the health ! :)

Other indoor museums or walking tours. Check out on Visit Estonia the museums and tours that might interest you. I suggest the Estonian History Museum and Kiek in de Kök Museum and Bastion Tunnels.

Christmas Market – no need to introduce, I guess. Try a hot wine with traditional Estonian alcohol – Vana Tallinn. God, we miss it!

Kompressor – one of our favorite spots, where one can enjoy a decent pancake.

III Draakon (Town Hall) – don’t leave Tallinn without trying an elk soup or a sausage in the Medieval restaurant. Budget friendly and delicious!

Rukis – a perfect place for coffee and a pastry!

NoKu – a half-hidden pub, a place for stand-ups and a good cocktail. You’ll thank us later.

Any place around Telliskivi Loomelinnak and Rotermanni kvartal – pick a place whichever you like!

If you are into a thorough planning, nothing is as informative and complete as the official site VisitEstonia. This post is my homage to Tallinn, I do hope, you will love it too and won’t get bored there even in the winter cold. Just remember to dress well! Don’t forget that you can open the map by clicking on the “full screen button”. All the places as well as the restaurants are indicated there. :)