A few years ago I was at a dinner party in New York City where we discussed our favorite places in the world. Most of the answers were exactly what you would expect—Hawaii, Australia, Costa Rica, etc. Then a guy who traveled to almost every country in the world said Tallinn, Estonia. I'm embarrassed to admit that I barely remembered Estonia was its own country, so its largest city and medieval capital wasn't even on my radar.
Before the plane even took off, I was in love with Tallinn—a round-trip flight from London is under a £100, a taxi from the airport is less than €15 and a room in a 4.5 star hotel is less than $100 a night.
We stayed at Hotel Palace for 4 nights and even though our room was quite small, we really enjoyed the indoor pool/spa area after a full day of being on our feet (although I wished the jacuzzi was hotter). The hotel is conveniently located on the border of the old town, so we could walk everywhere.
To be fair, you could probably walk every street of the entire old town in a day; however, the real fun was in discovering all it's nooks and crannies filled with medieval architecture, traditional shops and beautiful viewpoints. Don't cheat yourself out of a fairytale ending—spend at least 2 nights/3 days!
Before you get caught up in the rabbit warren of cobblestone side streets, spend a few hours walking the wall of the old town which brings you around the major sights of the city and provides panoramic views. Start at Pikk Hermann (Tall Hermann Tower) located at Toompea Castle. After seeing what the English call castles, I think the term is used pretty loosely in this context, since the building is actually a salmon-colored palace housing the Estonian parliament.
While you're on Toompea hill, check out the Alexander Nevsky Cathedral, a beautiful orthodox church. Despite it's dramatic exterior, you can see the entire church by just stepping into the doorway and it's free to enter.
Next up are a couple towers built in the 1400s: Kiek in de Kök and Maiden Tower (Neitsitorn), followed by the most famous of the wall's towers, Viru Gate (Viru Värav).
I found the area around Viru Gate to be less charming than the rest of the old town because it's relatively crowded and overflowing with tourist shops. With that said, if you take a little detour outside the gate and venture into the modern city, there's a local spot called CafeTroika where you can get pelemini, Ukranian dumplings. I was on a quest to find some because they're one of my favorite childhood foods and I was not disappointed despite the lackluster service.
The modern city isn't as aesthetically pleasing as the old town, so you'll want to get back on track and check out Nunna, Sauna and Kuldjala Towers.
Lastly, after a walk (and shop) down Pikk Street you'll come upon the Great Coastal Gate (Suur Rannavärav) and Fat Margaret's Tower (Paks Margareeta).
After you've walked the wall, you may want to chill out at one of the many cafes with a cold beer or head to my favorite spot in Tallinn—Olde Hansa. Firstly, I was really against going to a medieval-themed restaurant because I thought it was going to be terribly kitschy and over the top, but I was wrong. Olde Hansa ended up being my favorite part of the trip and I dragged my husband there daily for it's festive atmosphere and cinnamon beer.
Everyone is in character, but without putting on a show and all the details from the hand blown wine glasses with spikes on the stems (so men with greasy fingers wouldn't drop them) to the dinner menu to the instruments played by the medieval musicians are striving toward historical accuracy. As a medieval history buff, I was in heaven! Make sure to go Tuesday-Sunday to catch the music in the evenings.
A couple other restaurants where we had excellent meals for reasonable prices was: Kaks Kokka and Rataskaevu16.
If you're looking for something more to do after dinner than drink, you may want to check out the Estonian National Opera. The tickets are very affordable ranging from €20-30 per person. We thoroughly enjoyed a production of Rigoletto and were grateful that the operas are subtitled in English as well as Estonian.
For a further dose of culture, there's quite a few museums to explore, but I recommend heading to the Estonian History Museum in Great Guild Hall (€6 entry) to learn more about the city and culture. I love little museums like this with digestible exhibits that give you enough information to provide context without taking hours to finish.
We also went to the KGB museum; but I think it's one of those experiences you either love or hate based on how good your guide is. There's very little to see and the majority of the tour is based on storytelling. Maybe my guide wasn't on his game, but I was pretty underwhelmed by the entire experience and wanted my €11 back. The view from the top of the hotel was a bit of a consolation prize.
While there's a lot to see, do and eat, the real magic is just wandering the quaint candy-colored streets from another time. The old town looks exactly what I used envision as the backdrop to stories like Cinderella.
Make sure to walk through Katarina Gild, a street of stone buildings filled with artisan workshops where you can watch traditional crafts in the making and take home a truly unique souvenir.
I fell in love with the traditionally made leather notebooks (so much so I'm afraid to write in mine!) and everyday I look at that hand stamped dragon on the front and think fondly of my 4 day medieval fairytale adventure.