by Ucman Scher
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Townhall Square

Solo Gay Trip Guide to Tallinn – the Capital of Estonia

Tallinn is the capital of Estonia and it surpassed all expectations I have had for it. It was the last city on my Latvia Estonia trip and I will always remember Tallinn for introducing me to e-scooters. I can’t explain the thrill I felt the first time I rode. Tallinn is also very well developed and cosmopolitan capital with a huge penchant for technology. You might have an app in your phone that was born here; Skype.

Germans played an important part in the history of Estonia and Tallinn and a lot of the city was built by them as part of the elite. It is no surprise that Estonians aren’t big fans of this part of their history although I didn’t get any sense that they harbour any hatred for Germans.

Check out my country guide for Estonia for all your travel questions about this gorgeous country.

A happy me after the tour

Getting to Tallinn

Tallinn is very well connected and you can get here either by air, by ferry or bus. Rail connections between Baltic states are non-existent sadly. I arrived in Tallinn by taking an amazing tour which showed me a few points on the way. You can read about my Riga to Tallinn Tour here.

I left by the airport though which is called Lennart Meri Tallinn Airport (TLL). It is a small airport with a few amenities and very fast Wifi. (I was quite surprised as most airport Wifis are crap). The airport is situated quite close to the city centre. You can take bus 2 or Tram 4 from the airport to the city and the other way around. It is also quite cheap to take the taxi and if you are in Estonia you must use Bolt, another brainchild of Tallinn. I think it cost me €6 to go from the old town to the airport.

If you are coming by sea you can take the ferry from Helsinki or an overnight ferry from Sweden. You can check the schedules for these companies for more information; Tallink Silja and Viking Line (It also operates the Stockholm to Tallinn Ferry).

Telliskivi Creative Centre

Chilling in Telliskivi Creative Centre

Getting Around in Tallinn

Public transport is pretty good in Tallinn but you won’t need it. The old town of Tallinn is perfect for walking and everything is so close that you won’t care about taxis. For other areas, the tram service is good along with buses. Taxis are also quite cheap especially Bolt as I mentioned before. I used either Bolt Taxis or Bolt E-scooters which were absolutely awesome. Highly recommended!

Food in Tallinn

Tallinn has the best food out of all three Baltic capitals. The old town has a lot of great restaurants but I really liked two; Kolmas Daraakon and Rataskaevu 16. The first one is an old-style tavern and when I say old, I mean the barmaids will not acknowledge anything modern. You will sit and eat and drink by candlelight and expected to clean your table. The soup was great and so was the beef rib. Rataskaevu 16 is the exact opposite. It is modern and food is a modern take on Estonian cuisine. Highly recommended!

Check Out my Instagram Stories for the Estonia trip including restaurants and food.

F Hoone is another great place for brunch but it is outside the old town located in the Telliskivi creativity centre which is a great place to chill on weekends. Food is generally quite good and tasty throughout the city and I would also recommend trying pastries and desserts.

A happy me after some good food

Where to Stay in Tallinn

Old Town is the best place to stay in Tallinn. It definitely made my stay memorable. I stayed in a hotel very close to St Catherine’s passage in the old city which was ideal in all respects. Also, the lower town is much better for stays because it is livelier than the upper town.

Best Time to Visit Tallinn

Summer is the best time to visit and enjoy this beautiful city. Winters are pretty harsh and springs are a bit unpredictable. I visited in late May which was perfect weather-wise.

Lower Town Tallinn

Lower Town Tallinn

How Many Days for Tallinn

I stayed in Tallinn for 2 and a half days but you can easily do Tallinn in 2 days. I don’t think you can appreciate the beauty of this city on a day cruise and I highly recommend spending at least a night in Tallinn.

Gay Tallinn

Tallinn is an LGBT friendly city with a few gay establishments. X-Baar is the biggest and most famous bar here. You can check the updated list here. Tallinn also hosts the Baltic Pride every third year in rotation with Vilnius and Riga. Compared to Riga and Vilnius, it is much more open and friendly when it comes to alternate gender and sexualities. I guess it comes easy because of the lack of religious following here.

On Grindr, guys were also much more open with more face pictures and they also seem to be used to many foreigners visiting their city compared to Riga and Vilnius. I met one guy during my trip who was very nice and showed me around Toompea in the evening and told me about the third viewing platform, I almost missed. I would still suggest being cautious with PDA here though because there is no lack of nutjobs anywhere. I think Tallinn wins a major score for LGBT tourism compared to its neighbours, Riga and Vilnius both.

Free Walking Tour Tallinn

The Free Walking Tour of Tallinn was my first activity in the city and highly recommended. The guide explained the history, culture and language of Tallinn and showed us around the main spots. it was a very well-informed tour and in 2 hours I got to find out a lot of information.


How to Explore Tallinn

I have divided the list below into three parts; The lower city which is around the Town Hall of Tallinn, the second part is the Upper Town or Toompea Hill and a couple of places outside the old city. Apart from the last two places, you can easily explore the rest on foot without any issues. It does require some stairs climbing though because the Upper Town is much higher than the lower town (consequently amazing viewing platforms).

Top Things To Do In Tallinn

The Old Town of Tallinn

The old town is Tallinn is very beautiful and very well preserved. The cobbled streets and colourful houses nestled with churches and small shops make it a beautiful shape. It was also spared from the heavy Soviet bombardment. There are two parts and both are equally gorgeous.

A street in Oldtown

The Lower Town (All-Linn)

This part if called All-Linn and it is the busiest and most tourist part of Old Town. It starts from Viru Gate with city walls and has the Townhall of Tallinn at its centre. I walked around for hours and every small street has something interesting to offer. Getting lost here is the best way to explore this part of the town. The houses, the boutique type small shops, the cafes, everything is just adorable. I couldn’t get over it at all.

Viru Gate (Viru Väravad)

The Old city starts from the Viru Gate, it is the entry point most famous and looks the most medieval with the beautiful towers and a high city wall surrounding the old town. It is quite a busy spot with a lot of tourists coming in and out and lots of touristy shops. It did get quite calm in the evening though and in the evening light, it looks even more beautiful.

Veru Gate

Veru Gate

Hellemann Tower and Old City Wall Walkway

Entrance – €3

Right next tot he Viru Gate, I went up to see the views from the old city wall. I visited a couple of towers which had some interesting photos of old Tallinn. It was good to get some view of this part of the old city from the city walls.

St Catherine’s Passage (Katariina Käik)

It is a small passage and was literally a few minutes from my hotel. It is a great small street that gave me the feel of what it would be like to live in medieval Tallinn. There is a restaurant and some bars in the street but it is a quick stop otherwise.

St. Catherine’s Passage

Old Dominican Monastery Claustrum

This was one of my favourite spots in Tallinn. It is located very close to St. Catherine’s passage. The entrance is through an unassuming door through which you arrive into a lush green courtyard. It is so beautiful and peaceful, I spent quite some time here with my tea after breakfast.  There is a small museum inside that shows the monastery life but the courtyard itself is worth some time.

Dominican Monastery Claustrum courtyard

Dominican Monastery Claustrum courtyard

Tallinn Town Hall (Raekoda) & Square (Raekoja Platz)

The Townhall of Tallinn is a very imposing building with a grand tower. It is probably the tallest building around. It was built with stone in the 14th century. These days it has been converted to the Tallinn City Museum. There is no way you can skip this building. Most roads in the old town lead here.

Townhall of Tallinn

Townhall of Tallinn

The square around is the busiest place in the city. It has touristy restaurants, bars and everything you expect from the main town square of any European capital. I loved the colours of the buildings around, they were painted in such soothing but different colours. In the evenings, this area becomes quite loud but things get quieter. I remember walking here in the early morning and absolutely loved the quiet of the morning to enjoy the square in some silence.

St. Olaf Church

You cannot miss this church either. No matter where you go, you will see the tower and spire of this beautiful church everywhere in the lower and upper town. It is located in a relatively quiet corner of the old town and while its interior isn’t anything extraordinary, the church tower has some great views to offer. I decided against it though because I was heading to the Upper Town and you could get a better panorama from there.

Long Leg Gate Tower (Pika jala väravatorn)

It is a tower connecting the Lower Town with the Upper Town and a great way to go from one to the other without going through the outer edge of the town. It is made of stone and has the same old town charm. Right next to the tower is my other favourite spot; a small fountain waterfall with the statues of dears on Nuno street in the shadow of the city walls of the upper town.

My fav spot on Nuno Street

Short Foot Gate (Lühikese Jala värav)

Climbing up from the Long Leg Gate I arrived at the other side that leads me to Toompea Hill right behind the Alexander Nevsky Cathedral. It is also called Swedish Gate and the entire area around is perhaps the best experience of the old town. The gate and gate tower both are incredibly popular with tourists. I think this is the best way to cross between the upper and lower towns. The tower itself houses Hortus Musicus; an early music ensemble.

Toompea Hill

Toompea Hill

The Upper Town (Toompea)

Toompea or the Toompeais the upper part of Tallinn old town. It is quite high up and offers amazing views of the entire city especially the lower town. The hill has been the site of a Danish castle since 13th century. Through the years, it evolved separately from the lower town and became a spot for the privileged and aristocratic class. The conflict increased over time to such extent hat city wall was extended between the two areas with gates. There are three amazing viewpoints in the upper town, one with the oldest part of the wall and the other two with great views.

upper town Tallinn

Upper Town of Tallinn is equally colourful

Alexander Nevsky Cathedral and Parliament Square

Estonians are not big fans of the Soviet legacy from the time of occupation and that dislike extends to this onion-domed colourful Russian Orthodox church. It is quite prominent and stands right in front of the Estonian parliament building. The church is a typical orthodox building with lots of colours and definitely worth a look. While the Catholic and Protestant churches are not big on colours, orthodox churches are quite liberal with the use of bright colours.

Tall Hermann Tower (Pikk Hermann)

The parliament square in front overlooks the cathedral, the parliament and also an invite to the Tall Hermann Tower, the corner tower of the Toompe castle. The way to get to the tower is through the beautiful gardens. The view from the tower is also nice but there isn’t much to see since this is on the outer edge of the old city.

Parliament Square

St Mary’s Church (Toomkirk)

Another beautiful church worth a stop. The church was originally built as a catholic church but converted to a Lutheran church later. What’s intriguing is the beautiful interior filled with so many coats of arms very intricately designed and beautifully placed. This probably is my most favourite Lutheran church ever.

St Mary's Church, Tallinn

St Mary’s Church, Tallinn

Kohtuosta Platform (Kohtuotsa vaateplatvorm)

If you had only time for three spots in the city, I’d go here and the next stop would be Patkuli and Townhall Square.

Kohtuosta Platform panorama

Panorama of old city from Kohtuosta Platform

It is a small viewing platform that offers amazing views into the lower town directly. I lovvveeedddd this place. The spires of churches and Town Hall. I saw it the first time with the tour and then came back a second time in the evening when the day-trippers have gone. It was a beautiful evening and with tea and cake, the view became so much better. Tallinn is very very lucky to have these views honestly.

Patkuli Platform (Patkuli Vaateplatvorm)

This is the second panoramic point and offers different views of the town all the way to the harbour and the beautiful tower of St. Olaf Church Tower. There is a small cafe with some outdoor seating which was amazing to sit and people watch. I sat there watching the sudden influx of tourists with tour guides, the quick photos and selfies later, they are gone. I some times wonder if they actually see these place through their own eyes or is it only for the photos?

Patkuli Platform

Patkuli Platform

Linnamüür Platform

This platform is inside the Stable Tower and right behind the oldest part of the city wall. I don’t think it was worth going to the tower though and the view from the platform was beautiful.

Cannon Tower

Cannon Tower

Since I was around, I also had a look at the cannon tower, the museum inside was boring and honestly, there are so many spots where the whole medieval theme has been repeated throughout the Old Town of Tallinn you can totally skip it, I left after a few minutes.

The City wall between upper and lower town

The road leads to the Freedom Square and the Church of St. Nicholas.

St. Nicholas’ Church and Museum

Just outside the Old town, right next to the Tourist Information Office, St Nicholas’s church is another hard-to-miss buildings. It is a beautiful Gothic building and links the old town with the Freedom Square. It has been converted into a museum and there are regular recitals and concerts inside the church. Definitely worth a visit especially in the evening when there is less tourist. Space outside and around the church is also great for relaxing with a lot of options for eating nearby.
St Nicholas Church

St Nicholas Church

Freedom Square (Vabaduse väljak)

Freedom Square is the largest square in the country and quite important for national day parades. It is half modern, half old with a big cross on the right-hand side. There is an interesting story behind the giant cross which was supposed to be the star of the square but turned out to be an expensive mistake. It is not too bad but quite stubby. It is dedicated to the people who died during the first war of Estonian independence. The square is mostly empty with a few people going in and out of the old town.

The Estonian monument to the fallen people during the first independence war

Outside the Old City

Tallinn has quite a lot of green space and while a lot of the rest of town has a bulk of Soviet-era buildings, Tallinn is fast adopting modernity as the way forward. I particularly enjoyed these two spots.

Radisson Blu Sky Bar

I am not a big fan of hotel chains but this one offers the best view when it comes to Tallinn sunsets. I was in for a serious treat on the second evening when I headed to the sky bar in Raddison for a drink or two. The sun changed a million shades of red, orange and yellow and we sat there mesmerised. It was one of those moments when nothing seems important and all my problems seem irrelevant in the light of the blessings I enjoy, the prime being the ability to travel. I am not too sure about the food but the drinks were pretty good at the bar.

The sunset over Tallinn from Radisson Sky Bar

The sunset over Tallinn from Radisson Sky Bar

Telliskivi Creative Centre

The travel to Telliskivi centre requires an uber ride from the city centre but it is sooo much fun. I went on the last day with my friend for a brunch in F Hoone. It used to be an industrial complex and while the space inside has modernised, it has a rugged exterior which is beautiful in contrast with the interior. There are graffiti and wall art, small designer stores and studios, restaurants and open spaces and most excitingly, hammocks. It is quite a hip place with lots of trendy people going about. It was hard to imagine Skype being born in this city but Telliskivi centre totally puts that into perspective.

Wall Art in Telliskivi Creative Centre

Wall Art in Telliskivi Creative Centre

There is a lot more that Tallinn offers and you can do here, it might not be the hottest place for LGBT travel but only through exposure, we can increase awareness. If you want to enjoy a hint of Scandinavian culture mixed with Baltics ruggedness, Tallinn is definitely for you.



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