Tallinn old town free walking tour
Estonia,  Europe,  Reviews

Exploring Tallinn’s old town – Free walking tours in Tallinn

Compact it may be, but Tallinn’s old town has so much to see and do. During our stay we spent a lot of our time exploring this area, visiting some of the many sights and activities on offer within the old city walls. In my opinion, one of the best ways to explore a city is by foot (although in my instance this does involve a lot of café stops!) so whenever we visit a new city, one of the first things we do is see if there are any free walking tours.

Happily, we discovered these took place regularly, often led by local students looking to make a little extra money in the form of tips (and from experience I always think they earn them!). People meet outside the tourist information centre, where the guides then split you into groups and begin their tours.

Free Tallinn old town walking tours

Firstly our guide took us past a small modern park on Harju Street, introducing us to some of Tallinn’s tumultuous past. She explained that here once stood a row of houses that were sadly were destroyed in one of the big bombing attacks on the city in 1944.

This spot is overlooked by St Nicholas’ Church, which was also partly destroyed in bombing. Now fully rebuilt, it is home to the Art Museum of Estonia and is also often used to host concerts.

Tallinn old town free walking tour

The city has had a pretty tough time of it over the years, as we discovered when we moved along to Freedom Square and our guide talked about Estonia’s occupation by both Russia and Germany. However, the tales took a light-hearted turn when she told us more about the War of Independence Victory Column.

Discussed for decades but only finally completed in 2009, it appears this monument isn’t universally loved by Estonians, often due to the teething problems it had when it was officially opened. Firstly it was rather expensive – estimated at around €8.5m – as it has been said that it’s built from the world’s strongest glass, supposedly capable of surviving a nuclear attack. Then there were issues with many of its lights not working and finally, the most entertaining anecdote was the story that parts of the monument turned pink when dust managed to seap inside. Doh!

Beside the monument she pointed out one of the entrances to the Bastion Tunnels, which you can tour and which now also houses a carved stone museum. This intrigued us so much we booked a visit – but more on that in a future post!

Tallinn old town free walking tour

Kiek in de Kök

From the monument we headed up the stairs to the upper old town, where we got to see Kiek in de Kök in all its glory. And yes, I sniggered, but to be fair, this place has made it onto Buzzfeed’s list of rudest place names! A massive 38m high cannon tower, when translated Kiek in de Kök actually means peek into the kitchen, as from high up you could easily look down and into the neighbours’ houses.

In late 1500s, the tower was attacked by Ivan the Terrible’s army, which managed to badly damage the top storey. However, the tower survived the onslaught and during post-war repairs a row of four cannonballs was placed in the newly patched stone wall as a memorial, which you can still see today.

As with many of the city’s older buildings this has been turned into a museum. This one focuses on fortifications, weapons and medieval-era life.

Tallinn old town free walking tour

Tallinn old town free walking tour

Tallinn’s upper old town churches

Our next stop on the tour, after passing Toompea Castle, the pink parliament building, was the Alexander Nevsky Cathedral, a Russian Orthodox church, which I personally thought was one of the prettiest buildings in Tallinn’s old town. In the power struggle between Russia and Estonia it was built ‘bold and beautiful’ so that the country could see that ‘Estonia was Russian’. After independence Estonians considered demolishing it however, thankfully, they eventually decided against it.

In the upper part of Tallinn’s old town you’ve got two great viewing platforms that let you look out over the city and to the sea, offering some great photo opportunities. It’s also home to several churches, as we discovered when our guide stopped us in front of St Olaf’s, right next to one of these. Once known as one of the tallest buildings in the world (albeit a good few centuries ago), the first mention of St Olaf’s can be found as far back as the 12th century.

Over the years it’s reported to have been hit by lightning 10 times or more, and on several occasions burnt to the ground and rebuilt. You won’t find me hanging around on a stormy day, that’s for sure…

Tallinn old town free walking tour

Tallinn old town free walking tour

Tallinn old town free walking tour

I could have spent much longer exploring the little side streets with their gemstone shops and cute restaurants, but our guide told us it was time to head back to the lower area of the old town. Taking the 150+ steps down the limestone rock hill, we ended up at speaker’s corner. Here our guide told us more about the Estonian Language (including the fact it has over 10 different ways to pronounce nouns?!) and even got us having a go at speaking a phrase or two ourselves.

We took a slow stroll down the cobbled streets to the town hall square to end our tour. From here we were able to head off and explore even more of what the old town had to offer (consider this tour a taster – there’s still so much more to see!). But first we decided to potter around the square’s craft market and stop for a spot of lunch in the famous ‘medieval pub’ ill Draakon. Our guide thanked us for our time and sent us on our way but happily hung around to answer visitor’s questions about what we’d seen and where else she’d recommend we visit.

Why I recommend a free city walking tour

A great way to learn much more about the city you’re visiting, I’m a big fan of city tours – especially free ones, which appear to be growing in number. I find having a physical guide is much more informative and entertaining that a self-guided or audio tour, and – as with all the other free tours I’ve now taken, I’ve found the guides very friendly and helpful, with great English (putting our Estonian to shame!).

Prebooking on the Tallinn Old Town free walking tour isn’t necessary, simply check what times they’re running and rock up at the meeting point 10 minutes or so beforehand. There’s no charge at all, but if you enjoy the tour, why not tip your guide for introducing you to their city?

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Extraordinary Chaos

By day Co-Editor Keri is a freelance journalist and copywriter, but spends most of her free time either travelling or planning her next trip!  A complete travel fanatic, she has a love of tropical climates, wildlife and afternoon tea (hence the creation of her Global Afternoon Tea Challenge!)


  • Sandra

    Tallinn seems to be growing in popularity as a tourist destination. I would really like to visit the city before it gets too popular.

    • Keri

      Now’s the time to go then Sandra! It’s getting more popular for sure, but certainly not overcrowded when we went, which is good.

  • Caity Pfohl

    I always love checking out free walking tour options when I visit a new place. This looks like a great one and you had perfect weather for it, too! Definitely hoping to make it to Tallinn someday soon. 🙂 #mondayescapes

  • Esther

    I always love taking free walking tours, it immediately gives me a feel for a city, so I have a clue where I am going later on 😉 Tallinn is still high on my list to see, I would totally take this tour there.

  • California Globetrotter

    Would love to visit Tallinn! I think walking tours are such a great way to explore cities and learn history from a local’s perspective! #CityTripping

    PS. Just pinned like 10+ of your afternoon teas! How have I missed those?! I’m OBSESSED!

    • Keri

      Ha ha, there’s a whole section dedicated to them! I’m working my way around the world on my Global Afternoon Tea Challenge!

  • Usha

    I have come back from a trip to Tallinn and loved Tallinn. I absolutely loved the Old town. Would definitely go back there. Great post. #mondayescapes

  • Cathy (MummyTravels)

    I love all the history and architecture of Tallinn, somewhere I’ve wanted to visit for a while – the tour sounds a great way to appreciate it as well. I’m definitely making a note for when I finally get there. Thanks for linking up with #citytripping

    • Keri

      Hope you get there Cathy, it’s a really great city – think its a good spot for kids too – the maritime museum is amazing!

  • Kat

    Ooh Tallinn Old Town has a free walking tour – that’s great! I’m an advocate for walking tours and I love free tours too. However, because it’s free, there could be many people joining the tour. My last experience with a free walking tour was in Porto last September – unfortunately, the group was too big, the guide spoke and moved too fast that I didn’t get a chance to take good photos 🙁 #Citytripping

  • Emily Ray

    I bloomin’ love a good walking tour! We went on one in Havana and it was perfect for introducing us to things that was right on our doorstep. Love your photos of Tallinn too – we’re contemplating going later this year. How long do you reckon you need there? I’ve heard from many people that it’s quite small/compact, so would 2 days be enough? xx

    • Keri

      2 full days would definitely be enough – you can easily fill 3 though if you go further afield and spend time exploring all the museums! (there’s a lot!)

      I had no idea there were walking tours in Havana, damn that would have been good…

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