
If enjoy a Renaissance festival or have a general affinity for Medieval atmospheres, Tallinn should be on your travel “to do” list. Tallinn is also an excellent spot it you want to avoid those over commercialized destinations where tourism has diminished what once made the place so desirable to visit. While almost anyone that goes to Europe goes to London, Paris, Barcelona, etc., how many of your friends know what it’s like to explore a well-preserved Medieval town in Estonia? What might surprise you is that everyone in Tallinn speaks perfect English. I’m not talking about broken English with a thick accent that you have to try to decipher, I mean better-than-many-Americans, English. On top of all that they have a great pub and craft beer scene, restaurants that are safe for any American palate are plentiful, and they enjoy and welcome American tourists.
We visited Tallinn for 4 days in mid-January. For those that are not familiar with the geography, Tallinn is almost on the same latitude as Anchorage, Alaska. Yes, we were expecting bone-chilling temperatures; however, we were lucky. While the temps were in the high teens to high twenties, we had blue, sunny skies for our entire trip. Further, being off-season, we had the romantic, incredibly well-preserved, vibrant Old Town of Tallinn literally all to ourselves.
A trip to Tallinn is all about the Old Town. There are a couple of other sites to see outside of Old Town, but you should plan on spending about 90% of your time exploring inside the incredible Old Town walls. Tallinn’s Old Town is clean, safe, and remarkable. Ornate, mostly 14th – 16th Century original structures line the cobble stone streets in various shades of beautiful pastel colors. Occasionally you will see a stone structure from even a few hundred years earlier, and of course the churches sprinkled throughout are magical to visit. Tallinn’s Old Town is wonderfully preserved and begs for constant pictures at every turn. You could film an episode of Game of Thrones – or any number of shows of that ilk- without really having to do much if any alteration or enhancement.
Highlights and Things to do in Old Town Tallinn:
Reminder how it works:
Go!Go!Go! = bucket list travel experience, do not miss it for any reason.
Go!Go! = memorable, exceptional, highly recommended.
Go! = worth doing, you’ll definitely enjoy it.
No!Go! = Wasn’t for us.
Town Square: Go!Go!Go! We were so fortunate to be visiting in January with best case scenario weather. There were no crowds or tourists getting in the way or polluting our visuals. Like any main square in Europe, the late spring, summer, and early fall months mean you will be sharing the beautiful surroundings with hoards of others, so if you do travel at that time always try to get up early – at least one day – so you can try to see the Town Square as empty as possible.
The most noticeable building in the square is the Raekoda, or Town Hall. The building dates from the 13th Century and is in remarkable condition, as it is still used to host concerts and houses a small museum. Located just to the left of the entrance to the Raekoda is the polarizing III Drakon Pub, which I discuss below in the restaurants and pubs section. Across from the narrowest house on the far corner of Raekoja street is a working pharmacy that dates back to the 1400s. It is worth a peak inside as well as a quick walk through the little attached remedy museum.
















Toompea Hill: Go!Go!Go! Most European cities, especially in Eastern Europe, have a hillside section of town which is where the castle is located and where the nobility lived back in the day. Now, these areas offer amazing walks, wonderful scenery and even better views. This is another must do – we spent two, half-days meandering around and exploring the area. As with most hilltop areas, there are some incredible, regal buildings to admire as well as some adorable streets and squares to explore. Best of all, the viewpoints over the red rooftops of Tallinn are breathtaking.
A WONDERFUL WALK! Go!Go!Go!
For an absolutely perfect walk up and around Toompea Hill that’ll be a highlight of your trip and a magically memorable travel experience, start by heading down Nunne street from central Old Town. Take the long but gradual staircase to your left as you begin to arrive in the park area. After winding our way up the incredible staircase you’ll first come across the Patkuli viewing platform and then the Kohtuotsa viewing platform. Between the two viewpoints are narrow, cobblestone streets full of cafes, boutique shops, museums, and beautifully preserved estates. From the Kohtuotsa platform, make your way to Kohtu street which will take you to St. Mary’s Cathedral. Turn left onto Piiskopi street and walk down another block or two to reach the amazing Alexander Nevsky Cathedral. If the weather is nice, the Domberg restaurant/pub on your right has great outdoor seating. I wouldn’t eat there unless you’re starving, but it’s a great spot for a beer and people watching and to break up your walk. After admiring the Cathedral, head downhill to perhaps my favorite spot in all of Tallinn, the haunting and mystical Danish Kings Garden (Jardines del Rey Danes) Go!Go!Go! Between the Medieval wall, the wall tower, the view, the brilliantly creepy statues, and the overall movie-set atmosphere, you’ll want to spend an hour or more here taking pictures and soaking in the landscape. Be sure to climb the wall and have a drink at the Café Dannebrog. Is there a more unique entrance to a cafe? When ready, wind your way down the narrow stairs to the walled and cobble stoned Pikk jalg street, which guides you directly through the fabulous Long Leg Gate Tower and right back to where your walk started. It’s an amazing loop and makes for a perfect half-day in Tallinn.

















Alexander Nevski Cathedral: Go!Go! I was thrilled to get to see this cathedral. We’ve enjoyed so many different and unique places of worship during our travels, and yet we hadn’t seen a traditionally Russian cathedral with the famous Hershey Kiss spires. We walked in briefly while they were conducting a service, but mostly we just enjoyed the magnificent architecture from the nearby park and (the best view) from the top floor café of the Kiek in de Kok museum.



Although we chose not to go, if you do enjoy visiting churches or cathedrals during your travels, don’t miss St. Mary’s Cathedral or St Olaf’s Church. St. Mary’s is in a lovely, quaint section of town up on Toompea Hill with a number of nice little restaurants with outside seating nearby. Olaf’s Church is on the far north side of Old Town. Every European town has the church in the center of town where you can climb the endless staircase to the top for incredible views – Olaf’s Church is that church in Tallinn!


St Catherine’s Passage: Go! This short street provides convenient passage between two main streets in Tallinn Old Town, but the street itself is a historic gem. I love a good Medieval street, and St. Catherine’s Passage has narrow stone walls, cobblestone streets, overhangs, iron doors, arches, tombstones, and more. If you are looking for a souvenir, the Passage is home to the St. Catherine’s Guild, which is a collection of craft workshops where artists use traditional methods to create and sell glassware, hats, quilts, ceramics, jewelry, and other items. It is a must do as you walk around Tallinn.



Town Wall / Viru Gates / Hellemann Tower: Go!Go! Tallinn has one of the more complete and best-preserved old town walls in Europe. There are numerous viewpoints and several areas where you can walk along the wall and soak in the Medieval charm of Tallinn. My personal favorite were the 14th century walls known as Tallinna linnamuur, and the Hellemann Tower accessed just passed the Viru Gate. A must do while in Tallinn.




Kiek in de Kok: Go! The Kiek in de Kok museum, in addition to the humorous alliteration, offers a wonderful glimpse into Tallinn’s history. Located in a restored cannon tower along the incredible remains of Old Town’s wall, Kiek in de Kok has hidden tunnels, great atmosphere, and could easily double as a Game of Thrones set. While the museum pieces are fine – nothing too impressive – climbing up and around the tower and the views out the windows are worth the admission alone.




Tallinn Museum of Orders of Knighthood: Go! While we aren’t big on art museums, we do enjoy a quick stroll through quirky or unique museums. We only spent about 30 minutes here but enjoyed browsing through the quite incredible and historically significant private collection of regalia and symbolic badges. Knowledgeable staff and good explanations in English.

Monet2Klimt – If it weren’t January and 18 degrees we probably wouldn’t have stopped here. We probably would have chosen to spend the time in a park or sitting outside at a café; however, given that we needed some indoor activities, we gave Monet2Klimt a shot. Basically, you step inside a bare room with some random seating that has a 360-degree movie screen surrounding you. They play relaxing music and gradually morph in and out of famous pieces of art. It is relaxing – to the point we started having trouble keeping our eyes open – but it’s a bit gimmicky. If you like the art work and want a peaceful reprieve from the city, it may be worth a stop, but I would not recommend making it a planned stop while visiting Tallinn

Although we didn’t make it out of Old Town during our stay, there were two attractions with nearly perfect reviews that we hoped to see. We would recommend anyone planning a trip at least look into these two attractions:
- Kadriorg Art Museum – We loved the pictures of the colorful building and gardens, but we couldn’t quite find the time in our itinerary to make it the 10 mins taxi ride out to where the museum is located. At the same site is a museum and former house of Peter the Great.
- Seaplane Harbour Lennusadam – Also about a 10 minute drive from Old Town, right on the water, is this unique museum. With over 10,000 reviews and a 4.7 review on Google, you are almost guaranteed to enjoy it if you can make it!
WHERE TO STAY
Hotel Schlossle – Go!
Tallinn has a number of great hotel options right in Old Town. I would definitely recommend staying in Old Town since you’ll want to be in that area at least 90% of the time – plus it’s just more magical to stay in that area. However, be careful not to stay right at the main town square or nearby a major street like Rataskaevu – especially during the high season, Tallinn is like other European cities, particularly Eastern European and Mediterranean cities, in that it has a very active and very loud late-night club scene. Unless you want to sleep to the sound of thumping base, find a hotel in a quieter section of Old Town.
We stayed at the Hotel Schlossle, which at the time was the only 5-star hotel in Old Town Tallinn. It’s about a 5 minute walk north of the center of Old Town, which means it is far enough away for a peaceful night sleep but an easy walk to anywhere you want to go. We booked a suite with a separate living area, which is another one of our “must do” travel tips for couples, specifically on the first couple of nights after the overnight flight. If and when jet lag sets in, it’s so nice to have a separate room to go to so you don’t have to bother your spouse.
In addition to the ideal location, Hotel Schlossle is full of character, is very nicely appointed (particularly the public areas), had a very nice breakfast in an awesome cellar setting, and the service was excellent. We had nothing to complain about and feel perfectly confident recommending to anyone to stay there, but it stopped short of being one of those memorable stays where we would politely insist that you HAVE to stay there. The room itself was lovely but nothing uniquely memorable like some of the other hotels we’ve enjoyed in the past. No spectacular view, balcony, enormous shower, incredible breakfast, architectural feature, design, or other feature that transforms the hotel from a place to stay to a travel memory in itself.





BARS, PUBS AND GOOD LUNCH/SNACK RESTAURANTS AND CAFÉS
Tallinn is a solid beer city, with several breweries and craft beer bars stocked with countless bottles you’ve probably never seen from throughout Eastern Europe. As a beer lover, I was thrilled with the wide variety of beer to try, the quality of the beer, and the time warp atmosphere of a few of the beer halls and restaurants. Of course, being Eastern Europe, there are also a good number of cocktail bars and clubs for those interested in the late night scene – we are not.
III Draakon – Either Go!Go!Go! or No!Go! In other words, this is a very polarizing place. On one hand, the pub is quite literally a time machine that takes you immediately to the middle ages. It is located in the church in the center of town square, as it has been since the 1400s, has dragon signs, and feels like a set created for Game of Thrones. From the self-service pickle barrel to the staff in maiden outfits to the type of beer and food selection, to the fact that they only accept cash, they have done everything possible to recreate an authentic trip to a Middle Ages pub. For those that like unique experiences and authentic Medieval atmosphere, it does not get much better than III Draakon. It is likely the ultimate Renaissance Festival destination! The downside, and the reason many people don’t enjoy their visit to this pub, is that in their attempt to be authentic, they have coached their waitstaff to act as waitstaff did during that time. In other words, annoyed, indifferent, and unhelpful. Go in there with a friendly smile and ask a few questions about the menu and expect to be met with an eye roll and a dismissal along the lines of the Soup Nazi. Do not make small talk, and for Heaven’s sake don’t complain about anything. If you go, just soak in the atmosphere, try a pickle, have one of their odd but time-appropriate herb-flavored brews, take a few pictures, and enjoy the unique experience. If the service approach bothers you, you may hate this place, but if you go in with the right mindset, it may be one of the more enjoyable stops on your travels.




Koht – Go!Go! This was my favorite bar in Tallinn. While Ill Draakon was certainly unique in its ambiance, I didn’t love the rude service and the only beer they had tasted like rosemary. Koht made us feel like we had found a secret Medieval Speakeasy. I only wish we spent more time there as none of the bars after it were as special. It is hard to find, as the unmarked, tiny, entrance door is hidden off the main street in an alley next to the garbage receptacles. Sometimes a quest to find a place adds to the enjoyment once you are there, and that was true of our experience with Koht. If you do find the door, duck your head, step through, and enter into a cozy, tiny pub with a fireplace, hobbit-size doors, and a great beer selection. There is even a bottle shop next door. Loved it, fantastic!





Pierre Chocolaterie (“Choco”) – Go!Go! Located in a super cute square (in better weather months they have tables set-up in the square), we stopped here as a final stop after a great night of bar hopping and just walking around the romantic and nearly empty streets of Old Town. The service, slice of cake, and the hot chocolate were all outstanding. We loved the whimsical décor as well. This little café is a perfect stop for an afternoon snack or as a night cap.
Maiasmokk Café – Go!Go! Every European city has its “Grande Dame” coffee shop. The one that has been a town staple for decades and maintains the original charm that first appealed to customers. In Tallinn, Maiasmokk is that must visit café. With beautiful wood décor and a gorgeous ceiling, Maiasmokk also has excellent pastries and all the coffee and tea options you need. For anyone that relies on that mid-afternoon caffeine pick-me-up, make this a must stop. This should go without saying, but don’t get it to go…grab a table and feel like you’re back in the late 1800s.


Hell Hunt – Go! Solid gastropub with a very pleasant outdoor patio. While its modern, renovated décor jolts you back from the time warp that is Tallinn, it’s a good place to stop for a beer break, which is what we did. One of the better draft beer selections in Tallinn and better food options.
Kohvik Dannebrog Café – Go! Located just down the defense wall walkway from the Maiden Tower Café, the Dannebrog Café is all about the surrounding atmosphere. I wouldn’t eat here, but it’s a must stop for coffee, a beer, maybe a pastry or quick snack. Starting at ground level and walking up the steep stairs to the walkway on the wall and then making your way to the small, nondescript entrance is a fun experience. Grab your order and then head out to one of the outside tables to enjoy he view and pretend you’re in the latest Robin Hood movie.




Maiden Tower Café (Kiek in de Kok Café) – Go! The Kiek in de Kok museum, in addition to the humorous alliteration, offers a wonderful glimpse into Tallinn’s history. Located in a restored cannon tower along the incredible remains of Old Town’s wall, Kiek in de Kok has hidden tunnels, great atmosphere, and could easily double as a Game of Thrones set. The modern looking café with its signature world clock centerpiece is located on the top floor is a stark contrast to the rest of the museum. It is just a simple café with snacks, coffee and basic drinks, but the views are excellent – particularly the view of the Alexander Nevsky Cathedral. During warmer months there are lots of outside seating.

Beer House – Go! This place is admittedly touristy, cheesy, and could basically double as the German restaurant at Epcot®, but it’s fun. They of course have a full menu of German-style beer options, and it’s a nice recreation of a German beer hall. Their dunkel hit the spot. I wouldn’t go here if you only had a night or two in Tallinn, but we just stopped for a beer and enjoyed our visit.




Drink – Go! Casual, sports/beer bar with a nice selection of draft beer and a fridge full of craft brew bottles. We had one beer here, nothing to complain about and a nice stop close to the main entrance into Tallinn Old Town if you’re bar hopping.
Karja Kelder – Go! Cozy, very traditional pub in a cozy stone cellar atmosphere. Standard pub fare, and few good beers on tap. Nothing too special but a good stop by the Old Town entrance for a beer.


Depeche Mode Bar – As they say in Arrested Development, it’s exactly like it sounds. This cocktail hipster club/bar is an ode to Depeche Mode. Obviously if you’re not a big fan, no real need to go.
NoKu – No!Go! This is a popular and well-reviewed bar on most travel sites, with a laid-back, bohemian vibe. For us, the best part was finding it, as it’s hidden without signs behind a nondescript door on Pikk street. If you don’t know the code – 2580 – you won’t get to enter. NoKu prides itself on being a place for intellectuals and lively conversations, which isn’t a good fit for us. Yes, I know what I just did there. When traveling, we’re looking to try local beer, enjoy a unique or historic atmosphere, and have a good time. NoKu was more of a place you’d expect to find slam poetry or literary debates amongst college hipsters…so it wasn’t for us.
Brewery Olleklubi – No!Go! While I typically enjoy anyplace with “brewery” in the title, this place is a cheesy bar without any character or memorable qualities. We walked in, waited a bit, ordered a beer, waited a while more, and then just left.
Dinner Restaurants
Where to eat dinner is, in my opinion, one of the most important decisions to make when traveling. Sometimes you just have to grab a quick lunch while you’re site seeing, and breakfast is usually at the hotel, so dinner is the best opportunity you have to sample what the best chefs can do in that city and to get to know what kind of food drives the culture.
We had 4 nights in Tallinn, and therefore got to pick four restaurants.
Rataskaevu 16 – Go!Go!Go! Simply fantastic. Fresh, local ingredients that pop with flavor the second they hit your taste buds. If you have the notion that Eastern European food is bland or all dumplings and fried food, this place will immediately change your view. Colorful vegetables, delicious fish, bread to die for, and numerous modern takes on Estonian favorites all creatively plated and expertly prepared. Add that to a romantic, renovated but cozy vibe and a great beer and wine menu, and you can see why Rataskaevu 16 has a perfect 5 circle rating on TripAdvisor with over 7000 reviews!! It has been rated #1 for years and deservingly so! Your first reservation after booking your flight to Tallinn needs to be at this restaurant, don’t miss it!





Restoran MOON– Go!Go!Go! Located only a 5-minute walk from the north side of the Old Town Walls, MOON is a must do to experience a little traditional Kremlin cooking. For us, one of the most important and enjoyable parts of traveling is to experience some traditional culinary favorites. Restoran Moon serves fresh, farm-to-table, flavorful versions of traditional Russian and Eastern European classics. They had everything I wanted – blinis, dumplings, borscht (incredible), chicken Kiev, pickled cucumbers, and so much more. Cute atmosphere, excellent service, and low prices round out a perfect spot for dinner.






Von Krahli Aed – Go!Go! Foodie lovers will love Von Krahli Aed. This place is all about organic, quality ingredients prepared simply and with a nod to traditional Estonian favorites. Von Krahli Aed is a perfect choice for a romantic dinner, reasonably priced, with a good wine list, and with knowledgeable and helpful staff (that speak perfect English).



Porgu – Go! Located right on a busy street with lots of other nightlife options, Porgu is the fun, lively, atmospheric favorite for both tourists and locals. Porgu is an excellent pub with numerous Estonian and European craft brews that also happens to serve high quality, traditional food options. Favorites include the borscht, fish soup and the pork chop. The large, gothic arches really added to the ambiance. Even if you do not have dinner here, it is a must stop for a beer or two at the bar.


Old Hansa – Go! We had lunch here, but it would also be an okay choice for dinner. Old Hansa is the tourist choice when visiting Tallinn. Go to Restoran Moon or Rataskaevu 16 if you want world class food, but if you want that almost Disney® theme park atmosphere, Old Hansa is the place. From the waitstaff outfits to the drawings on the menu to the wooden tables, chairs and décor, everything at Old Hansa is there to make you feel like you time traveled back to the Middle Ages. Also, unlike III Drakon, they decided to bring one important part of modern society into the restaurant – good, polite, attentive service! Yes, it’s a bit cheesy and certainly a lot touristy, but the food is good, inexpensive, and the experience is one you just need to have when visiting Tallinn.






Texas Honky Tonk and Cantina: No!Go! To be fair, this place actually looks fun and gets very good reviews. That said, do not come to Estonia – or Europe in general – and eat Tex-Mex. Being from Austin, we couldn’t help but peak in the window, and it is an over-the-top caricature of a Tex-Mex restaurant, but I can definitely see how the locals or even European tourists would find it fun. While not as egregious of a travel crime as eating at the Hard Rock Cafe or somewhere like that, there are just too many other great restaurants in Tallinn to eat something you can find easily in the US.

Note: If you’re looking for fine dining options in Tallinn, there are several with excellent review scores that we were not able to try during our visit. Particularly, take a look at Tchaikovsky.
One final note: there is one additional recommendation for Tallinn that should go without saying as it is a no-brainer. Just 10 minutes outside of Old Town Tallinn is the sea-port where in only 3 hours a ferry can drop you off in central Helsinki, Finland. While Helsinki could even be done as a day trip from Tallinn, scheduling 2-3 nights at each stop is a great itinerary.

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