Why it’s worth visiting Tallinn, Estonia
When I told people that we were going to Estonia, the most common response was: where?! And to be completely honest, I didn’t really know exactly where Estonia was located until I looked a little closer at a map when I was scheduling flights. And the reality of its location didn’t really sink in until we arrived: the country borders Russia and Latvia and is just south of Finland and east of Sweden across the Baltic Sea. So much of the food, architecture and design felt far more Russian or Scandinavian than the Eastern European I expected–and the days were also just as short and cold as you’d expect in a Scandinavian or Russian winter! 
One of the main reasons that I wanted to visit Tallin was because of its beautifully-preserved medieval city: the entire walled Old Town is a UNESCO World Heritage site. The second reason was to experience my first European Christmas market. Another fun fact about Tallinn: it has more startups per capita than any other European city, and Skype was invented here! It didn’t disappoint: I loved wandering around the ancient cobblestone streets, drinking glogi (mulled wine!) under the Christmas tree in the town square, and eating all of the delicious food. One thing I will say upfront: although it was so festive during the holiday season, I would 100% recommend visiting in summer or shoulder seasons over winter. I was dying to experience the 24 hours of daylight and enjoy all of the lush forests that surrounds the city, but then again, no surprises that I’d rather not be somewhere cold, ha! Just another reason to go back…
What to Do
Stroll around Old Town…
Honestly, my favorite thing that I did was just wander around the walled Old Town: it felt like you had been transported back in time to hundreds of years ago. I’m such a sucker for those narrow cobblestone streets and Gothic architecture: it’s all wonderfully preserved, and it felt like a fairytale city!
…and the hipster neighborhood of Kalamaja
It’s definitely a different vibe from Old Town, but I do recommend getting out of the city center at least once. It’s a lot less touristy once you cross over the medieval wall! We loved the laid-back restaurants, bustling markets and cool home boutiques in Kalamaja, which is one of the younger, more hipster-y areas. On my note about visiting Tallinn in the summer: I especially loved an area that was full of picnic tables and container bars and fairy lights. I can only imagine how much it comes alive on a long, hot day! 
The town’s main square
We visited in late November, and the main square had already been taken over by the Christmas market! There was a giant Christmas tree and stage, and stalls selling mulled wine and sausages and all sorts of hand-woven scarves and socks and hard-carved wooden trinkets. 
See a view of the city
For a lovely view of the city’s red rooftops and towering church spires, head to the Kohtuotsa viewing platform. It’s super accessible and easy to find–and free!
Enjoy all of the colorful doors
The most unexpected highlight of Tallinn: all of the incredible doors in Old Town! They were so colorful and intricate: such a nice little detail that really set certain residences apart.
Admire the Orthodox Russian cathedral
One of the things that made me realize how close Estonia is to Russia: the towering Alexander Nevsky Cathedral that’s located right across from the Tallinn parliament building. I loved seeing the cupolas pop up over the surrounding architecture!
Where to Eat & Drink
First and foremost: THE BROWN BREAD. I don’t usually like brown bread very much (I’m truly only committed to sourdough) but I couldn’t get over how delicious Estonian brown bread was. It was served warm and SO soft, and always accompanied by the most incredible melt-in-your-mouth butter. Truly, I’d go back to Estonia for the brown bread alone. 
For coffee and pastries, you must head to Tallinn’s oldest cafe: founded in 1864, Maiasmokk feels like a little slice of a different era of coffee shops. I didn’t spot one laptop while I was here: just people chatting over cappuccinos. It was delightfully refreshing.
The most recommended restaurant by far was Rataskaevu 16. We made reservations here for Thanksgiving day (and along with every recommendation came the urging to make a reservation!), and although it wasn’t quite turkey-sweet potato-and-cranberry-sauce, it was a thoughtfully-prepared and delivered feast. There were lots of Russian and Scandinavian influences at play here, with beets and sour cream sauces and smoked fish–and we loved them all. Another thing that struck me in Estonia was how friendly and helpful all of our servers were: it felt like everyone really wanted to ensure that we had the best possible experience.
I went to Estonia with my husband and his best friend, and Von Krahli Aed was maybe the best restaurant for all three of us to truly enjoy. The menu is creatively designed for both omnivores and vegetarians to enjoy: every entree has both a meat and a vegetable-only option. As someone who would almost always eat more vegetables than meat, I loved that there was such an array of veggie-forward options–without having to drag the guys into going to a vegetarian cafe that they wouldn’t enjoy! Another place with delicious brown bread: it came with salted pistachio lactose-free butter, and I can’t even come close to describing how good it was. The perfect place for a meat-lover and vegetarian compromise! 
For breakfast, loved the laid-back vibes of Boheem. For the porridge option, you could choose your grain! I cracked under pressure and went with oatmeal, but I wish I would have tried a different type of Estonian grain. Alas!
F-Hoone is a cavernous space that somehow manages to feel cozy: it’s a great place to curl up with a drink and chat with friends, especially over the decadent charcuterie plate.
And for a casual beer, we loved the beer garden vibes and excellent beer at Beer House. The only disappointment was that there weren’t any proper German pretzels!
Where to Shop
I popped into several boutiques in Old Town, but my absolute favorite was the Labora Card Shop. There were all of these incredible handmade paper cards: serious upgrade on the postcards you can send home. I especially loved the cards that were made of seed paper: you can actually tear up the card after you receive it and plant it and wildflowers will grow!
Balti Jaama Turg is a giant market space that has just about everything you could dream of: a grocery store, pharmacy, produce vendors, a meat section, clothing, and lots of trendy prepared food stalls. I only wish we had discovered it before our last day: there was so much that I wanted to try!
Where to Stay
Located in the heart of Old Town, the best part of Hotel Telegraaf was definitely the pool, sauna and spa. Like much of Scandinavia (and anywhere that has chilly temps for most of the year!), Estonia is definitely a sauna culture, so it’s well worth double checking to ensure that your hotel has one: it’s perfect way to wind down after a long day of exploring the city.
