No matter how many times I write out the word Tallinn—which has been happening with surprising frequency lately—I always start by spelling it with a single ‘n’. That is neither here nor there, just a little personal potpourri to sprinkle in at the start of this post.
Moving on.
In terms of day trips from Helsinki, Tallinn is low-hanging fruit. It’s a relatively quick 2-hour ferry ride from one city to the other.
We compared the two main options: Tallink and Eckerö Line. The latter was significantly cheaper, though it’s known to be a bit less fancy. It likely won’t surprise you to learn we’re not fancy folks, so saving money made the decision easy.
Our apartment was technically located on the Jätkäsaari peninsula, which just so happens to be where the ferry departs from; it was a convenient 10-minute walk from our door.



It’s an 8-deck ship, and we headed straight to the top to watch it pull out of port. Unfortunately, there’s not a lot of extra seating, so by the time we got back inside it took a while to find a spot we could all sit down. Eventually we did, and I’m glad we prioritized getting great views to start the journey.

No one wants their picture taken while they’re in the middle of eating, but I simply include this photo—helpfully censored by Indy—to illustrate the fact we brought a picnic along. Fruit, sandwiches on rye bread (not the kids’ favourite, admittedly, but they powered through), and some doughnut holes.

The ferry ride passed quickly; we played poker as a family for about an hour and the rest of the time I read my book! E-readers for the win!
It’s a fairly short walk from the ferry terminal to Tallinn’s Old Town which we entered via the Great Coastal Gate. It was the primary gate for accessing the city, and Tallinn’s coat of arms is featured prominently.


The architectural contrast between Tallinn and Helsinki is palpable. It felt like we were in Old World Europe again!

That said, there are plenty of Soviet influences present in the area. Estonia was annexed into the USSR in 1940, and remained there until 1991. We didn’t go in (the building’s official name is Pagari 1), but this set of KGB prisons was especially notorious.

The Estonian flag.

We do love a good door picture! So much variety, colour, and patterning.

Every way we turned there were more picturesque cobblestone streets.

Here I am outside the House of the Blackheads.


We did a lot of wandering, as one does in an old city.

It was the day before Mother’s Day, so a portrait was in order.



I quickly lost track of which church was which (there are a total of five main ones, I think), but the old clock on the side of this one was very cool.

We were a bit confused by all the foreign flags flying around the city, until we realized May 9th—the day we were visiting—was Europe Day!

I’m a big fan of quirky stops and I’m a big fan of books, so I jumped at the chance to satisfy both curiosities by visiting the small (free!) Banned Books Museum. They had all sorts of banned books on display, along with the country in which the book has been banned and a short description of why. We didn’t stay a long time, but it was an interesting stop.

Not surprisingly, a lot of countries have banned 1984 by George Orwell!!

Ditto with To Kill a Mockingbird.

I was more surprised by the children’s books that were frequently banned. Winnie-the-Pooh. Black Beauty. Where the Wild Things Are.

Then there was Brown Bear, Brown Bear. The banning of this book had more to do with the author, not the book’s contents. Turn’s out there’s another Bill Martin (minus the Jr) who had written a book on Marxism… and the Texas Board of Education banned Brown Bear, Brown Bear out of protest against the wrong author!!! (They went on to reverse the decision when they figured out Bill Martin Jr was just writing about brown bears and… blue horses.)

Indy doesn’t approve of the ban!

After we left the museum, we wandered the streets for a while.



We stopped by St. Catherine’s Passage. This medieval walkway is very quaint and filled with cafes and artisan shops.


One section is lined with tombstones (from the 14th and 15th centuries) from a nearby churchyard. In 1874, the mayor of Tallinn picked out some of the best preserved tombstones and used them to pave the floor of a barn! And some of them are on display here…



Full credit to Belle for spotting this giant gnome. Indy and I couldn’t get across the street fast enough for a photo.


We seem to have a thing for statues in Europe. They definitely tick the quirky box. This one is called Black Angus and sits outside a… steakhouse.



Next up was Viru Gate. Built in the 1300s, it was yet another entrance into the Old Town.



My favourite part of the area wasn’t actually the gate, it was the flower market nearby. These blooms were STUNNING. There were so many different varieties of flowers on display and the prices were incredible. (I saw some people coming back on the ferry at the end of the day with giant bouquets.)




We headed toward another statue: Lucky Chimney Sweeper. Apparently, chimney sweepers used to have gold buttons on their uniforms (I have no idea why), and people considered it good luck to touch said buttons. So now the tourist shtick is rubbing the bronze buttons on the statue.


Next, we happened upon a major Europe Day festival. They had all sorts of booths set up representing various countries in the EU. We made the rounds and when we stopped at the Portuguese booth they were handing out fresh pasteis de nata! Yes, please.

I brought home a mini Danish flag to put up in our apartment for when my sister-in-law came to visit (stay tuned for a post about that!).

I don’t know what this is, but I’m assuming it’s a memorial!

A church.

A bookstore!

Cool houses!

We agreed this tree in the church courtyard reminded us of the Whomping Willow from Harry Potter.

Another pretty door!

I LOVED this sign on one of the souvenir shops. I didn’t actually buy or send any postcards from Tallinn, but if I had, I’d want it to be from here!

Vegan friends, rejoice!

We wandered up and down side streets and wondered why there was a long lineup outside this bakery (Karu Talu Sokolaad).

Question answered: these ENORMOUS cookies were for sale.

While I waited in line (you didn’t think I could resist, did you), I snapped this picture and sent it to Joy. “A friend is someone who likes you even though they know you.”
Praise the good Lord for that.

Love it! Talk to each other—hahaha.

There’s no indoor seating, but it’s incredibly quaint inside.

My family would say it doesn’t take much to impress me. This is the Town Hall Pharmacy in Tallinn which is the oldest continually running pharmacy in Europe (it dates back to 1422).

This is Oma Asi, a cute little artisan shop.




We took a quick spin through Town Hall Square.

This gate is called Long Leg Gate.

And this one is called, wait for it, Short Leg Gate. It was the sole pedestrian-only gate in town.



After we had walked for a while, we unpacked the GIANT cookie and split it 4 ways. One of the options gave you both styles of dough. It was delicious!

If we were going to take a break, why not take it in front of the beautiful Alexander Nevsky Cathedral, a Russian Orthodox church.




I think this sculpture had something to do with a school? It reminded me of Le Passe-Muraille (The Man Who Walks Through Walls) in Paris!

We spotted a Canadian flag in Estonia!

This cute little bakery is the oldest in Tallinn: Cafe Mathilda on the Hill. It was indeed on a hill.

There are two iconic viewpoints overlooking the Old Town. First up, Kohtuotsa viewing platform.


Indy’s turn.




And then we made our way (it’s very close) to the second: Patkuli Viewing Platform.




I remember this church was called The Dome Church!

This seemed like as good a spot as any to do a tree pose.

I like this door. The stone wall. The plants. The doorway. The stairs.

What goes up for the view… must come down. En route, we did the requisite statue poses.


And some feats of strength/anti-gravity!


We headed toward Balti Jaama Turg, a large market complex. The gorgeous archway at the entrance foreshadowed the incredible fruit we’d find inside!

Look what we came out with! Fresh strawberries, which were a perfect afternoon treat.


I had originally wanted to go to two more places: Seaplane Harbour (you can tour a submarine!) and Telliskivi Creative City (cool street art), but there simply wasn’t time. So we headed back toward the ferry terminal which happens to be right by Linnahall.
This event venue was built back in 1980 for the summer Olympics in the Soviet Union (Tallinn hosted sailing events) and it quickly fell into disrepair. Parts of Christopher Nolan’s movie, Tenet, were filmed here! There are plans for a renovation, but for now it’s… kinda sad but in a really intriguing way.





There were a few tourists wandering about (it’s freely accessible to the public), and apparently it’s a popular spot to watch the sunset.

By this point, we made our way back to the ship where we spent two hours laughing along to Finnish karaoke (truly hilarious, especially since we couldn’t understand anything, but some people get SO invested). We were tuckered by the time we got back to port, so it was an easy decision to rent scooters for everyone and save our legs from the walk home. It was a short ride—less than five minutes—but a fun way to cap off an adventurous day.

Your turn.
- Have you ever been to Estonia?
- Electric scooters: yes or no?
- Have you ever done karaoke. Sadly, my answer is still No.
Discover more from The Optimistic Musings of a Pessimist
Subscribe to get the latest posts sent to your email.




I’ve never been to Estonia, but I’ve heard it’s vegan-friendly! I’m intrigued about all the signs in English- I guess it’s widely spoken there? I love all the photos. It looks like a beautiful day in a beautiful city. Oh, I want to go to that banned books museum! Winnie the Pooh has been banned??? I would love to hear the story behind that one.
I’ve never ridden an electric scooter, but I would. No karaoke for me though!
It was such an interesting museum (and free!!).
I had to chuckle over the Brown Bear, Brown Bear mishap.
I think I’d love karaoke?
Beautiful, all of it! I am jelly you are somewhere that requires a jacket– I just sweated my way through an all-school field trip to a splash pad and feel like I may never be cool again.
We have definitely needed a jacket… a lot on this trip. I’d take a little more heat, actually, but do think it’s better to have cool weather over heat when travelling. I become a melted puddle.
Last summer I sent postcards from the shop you photographed. It was fun to send out the quirky Estonian-made cards! 🙂
What are the odds???
Never been to Estonia, but it looks beautiful! Never did karaoke and never will – I’d have to be drunk to get up there and I don’t drink!
My 12 yr old just bought an electric scooter – the boys really have fun on it. The students on the local college campuses seem to have a number of them as well. I tried, got about 6 inches forward, and hopped off. I could not balance. Such boring life I lead!
Your trip fit so much on one day! You do travel right.
I think I’d really enjoy karaoke??
Indy would LOVE to have an electric scooter. It is a bit scary! Especially when driving on the road beside cars. Eeks. I did it once or twice in Finland and that was enough for me. But the kids loved it.
I heart karaoke – I love singing and I don’t care whether there are other people. We also have the let’s sing game at home. Not proper karaoke, cause you sing along but still. Love it.
I’ve been in that corner of the world on a trip with my old folk dance group (mostly old as in I no longer am in the group). It was a lot of fun! We stayed with host families.
It looks like a lovely place to visit 🙂 also not a huge fan of electric scooters, mostly because they are used by younger kids here with no sense of how risky their behaviour is.
Electric scooters are literally everywhere in Finland. It was shocking! There are definitely pros and cons with them; most of the time people seemed very responsible, but John and the kids were out once and saw a group of teen boys (not to be stereotypical or anything!) who were not riding safely 🙁
I keep meaning to get a karaoke mic for home. I think it would get a lot of use. Belle, in particular, would sing all. day. long.
I have briefly been to Estonia! My favorite was the marketplace. We found so many fun things there.
No to karaoke though!
I’d definitely love to spend more time in Estonia in the future. And it was soooo inexpensive comparatively!
I’ve been to Estonia! It was the last stop on our honeymoon. We had a delayed reception in Romania with my husband’s family and then since we were on that side of the Atlantic we went to the baltics for our honeymoon.
The Baltic region is truly lovely. I’d really appreciate having more time to explore Estonia on another trip.
What a beautiful place – and there’s a giant gnome! A GIANT GNOME! What could be better?
I thought of you (and Nicole) immediately.
Oh, I would be ALL ABOUT that banned books museum. What a cool museum, and especially wild to see how many different books get banned and in what countries.
That cookie though. Mmm! I wouldn’t have been able to resist, either!
My favourite (I mean, in “the most unusual”) was Brown Bear. To have a book banned because you’ve been confused with someone else is just wild to me.
The cookie was so good. And huge!!!
Wowwww that looks so gorgeous!! And that makes me inspired to keep pushing on to read 1984, it’s been a slog and with the current political climate I had to put it down – it was pretty depressing.
That tree reminds me of a woman sitting there looking distressed, but definitely see the Whomping Willow vibes!
Some of the architecture is so gorgeous, it makes me desperate to get to Europe to see more. I’ve only been to Greece and that’s it (though I really, really enjoyed Athens). Thanks for sharing all the pictures!
I loved 1984, but haven’t re-read it in years. I would be fascinating to consume it in the current political and economic climate.
Europe architecture is unique and lovely. 10/10 recommend!