Before moving to Finland, I have to confess that I had never heard of Tallinn, Estonia. In fact, I doubt I could have placed it on a map. Now, just two years after living in Finland, Jimmy and I have visited nearly 10 times, in sun rain and snow. It always remains an option for a quick weekend or birthday get-away and is a must visit for any of our guests coming to stay longer than three days. (Funny that one of the top things to do in Helsinki is to take a ferry to another country…)
In fact, our first adventure in this little town was just two weeks after we landed here in the fall of 2014 and was, therefore, our first toe in the waters of European travels. And on that short weekend, we learned why it is that Finns just cannot stay away from Tallinn: Not only is it a fast and easy get-away for more affordable shopping and spa treatments, it is also their most favorite place to buy discounted liquor in mas quantities.
Mind you, the city has so much more to offer than warehouses of moderately priced alcohol. And in our nearly dozen trips down to the charming little town, we have fallen a bit in love with the terraced plazas and hidden side streets of Tallinn.
…and we may have brought back a few cases of beer.
The first thing to note about Tallinn is that the old town is entirely separate from the neighboring modern city of Tallinn. We spend our time in the charming, albeit touristy area of Old Town. That said, most months of the year, it is a city largely devoid of massive crowds and oblivious tour groups. It is a stop for most Baltic Cruise Liners, but the influx of cruisers is usually only present for a few short hours in the day.
We enter, always, from the ferry terminal. From there we generally skip the taxi line and make the easy 15 minute walk into the city walls. However, if you do decide to take a taxi, be sure to set your price before getting in the cab. Simply ask them to drop you in Old Town and they will try to get as close to the main square as possible, or at least leave you by the main city gate.
The best part about this little medieval gem is that it does not require a schedule in order to see the whole thing within a day trip. We generally rent an Air BnB and arrive on a late night boat, just in time for a late dinner and to enjoy the city’s vibrant (and uniquely hilarious) night life. Highlights always include a science lab-themed bar and club and a small bar in a random apartment building whose dance floor, until very recently, included a claw foot bath tub.
Then we spend the afternoon the following day wandering through the streets and enjoy the little terraces in the city.
My suggestion for the casual day-tripper is to start by approaching the Old Town Square from the north, which you will inevitably do if you are walking form the ferry terminal. These streets are particularly charming and are lined with small coffee, craft and curiosity shops. Eventually, enjoy Old Town Square and the medieval themed stores that line its perimeter. When it is time to move away from the lingering crowds, push southwest up the hill towards Alexander Nevsky Cathedral. Following the street Pikk jalg will take you up to the top of the city walls. Once on this hill, there are a few little churches as well as some nice lookouts to enjoy the rambling red tile roofs.
Our favorite place to pause is here- right at the city gate on top of the hill. Look up at the tall city wall and lookout before passing through the gate to the Orthodox cathedral; you may see merry drinkers sitting with a beer or cider on the wooden ramparts. You can access this wee little bar by going up the stairs inside the wall, to the left of the gate. Heads up: they are horribly steep and narrow. Don’t drink too much up at the top!
Once up there, you will be rewarded with a quiet perch to watch the city below. You may get to watch some people try their hand at archery on the lawn or listen to a local street performer.
One of our other favorite places to rest our feet and quench our thirsts is Olde Hansa. Just off the main square, this place is admittedly a total tourist trap. The waiters dress in medieval garb and ask if you want to pay in ducats; it is ridiculous but also very fun. We found ourselves in here on one trip in December as we were looking for a place to thaw our toes. The smell of cinnamon roasted pecans drew us in to the small room off the square, where we ordered mutton stew and large clay mugs of cinnamon beer, and dined by dim candle light. Since then, the nostalgia of that one time has brought us back on a few other occasions. For all its hoaky tourism, they do make great (large!) portions of food. And there is something so satisfying about cheers-ing those huge clay mugs!
We have also eaten in the main square and always had good meals, if only a bit over priced. However, I suggest getting a little far away from the main square for the best experience. The street called simply Pikk has a number of great options and is lined with umbrella-ed terraces on sunny days. On the triangular corner of this street is a charming coffee and sweets shop with beautiful window displays, Kohvik Maisasmokk.
Be sure to stop in some of the little shops along your stroll. There are plenty of great local crafts and woven goods for purchase. I bought a beautiful fur-lined hat last year and have been tempted by their embroidered Nordic sweaters on every occasion.
However, the best thing to do in Tallinn is to simply wander until you have found something that looks great to you. While wandering with my parents last fall, we were drawn into this adorable courtyard by floating lave music. We stayed to find a lovely jewelry shop as well as an amazing coffee and chocolate shop, where I had some incredible and rich hot chocolate. I have not yet been able to find this place again! (If you find it, comment!!) Despite our number of visits, we still run into new streets with enticing stores and menus each time we go.