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Free walking tour in Tallinn: A guide for first time visitors to Tallinn Estonia

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Why visit Tallinn Estonia?

Estonia has been on my list of places to visits since 2000.  Given how much time I’ve spent in Europe since then, I’m not quite sure why it’s taken me so long.  Perhaps though, it’s been a good thing, as Tallinn has grown up, out of its Soviet past.  It’s now dressed and ready for visitors, with a new moniker as one of the most exciting and beautiful countries in the world to visit.  Put it on your list!

It’s funny what sticks in your mind.  In 2000, I was working for Australia Post when a woman from Estonia Post visited us on a business trip.  As a business development manager at the time, I was charged with trying to bring new businesses on board for our bill payment service.  A process where people could pay their bills over the phone or online.

In 1998, this was relatively new in Australia.  It only took a few minutes of her talking to us for me to realise what a world-leader Estonia was in terms of technology.  In 1998, they were selecting carparks and paying for them with their mobile phones.  All bills had been paid online for many years.  By 2003, Estonians would be integral in the development of Skype and later Kazaa, a peer-sharing music network.

tallin old town sunset

Tallinn is a world leader in technology

In striking contrast to the former life they had lived under Communist rule, where strict rules stymied independent thought and creativity was non-existent, the new government was seriously progressive.  Instead of conforming to new rules or processes, the very young government with an average age of under 40, went straight to the leading edge.  It developed state-of-the-art digital phone technology which performed at such a level that telecommunications companies all over the world routed their own service through Estonia.

In the early 2000s, I bought a travel sim in Australia for use overseas.  It had an Estonian phone number, not an Australian one, as all calls were routed through Estonia.  Hi-speed internet access came shortly after.  Today, free wifi is available all over Estonia, even in some of the more remote parts.  It’s not hard to imagine after the government rules internet access “a human right”.

There is no doubt, that Estonia is an e-society, a leader in the digital world.  Estonians are e-people, with e-ID cards and online tax declarations are completed in a matter of minutes.  They vote online, with Estonia being the first country to have an online voting system that was legally binding.

Our Uber driver, en route to the airport, told us ” we have very clever people in Estonia and clever people come to Estonia to stay because we make it easy for them”.  He’s right, with the government also breaking down the barriers for start-ups and fostering entrepreneurial spirit and enterprises.  Is it any wonder this is such a forward moving country.

Tallinn still has some challenges

It’s not all a bed of roses, however.  After a long history of German and Soviet occupation, independence was only achieved in Estonia in 1991.  Challenges abound.  Estonia has struggled with unemployment.   There are cultural sensitivities between ethnic Estonians and Russian-Estonians, much of it caused by recent modern history throughout the occupation.  Whilst digital infrastructure is at the forefront of government strategy and spending, the opposite can be said about much of the physical infrastructure.  Roads are ok but don’t really connect where you think they should.

Tallinn – a perfect place to visit

Tallinn is a great place to visit for a few days.  If you only have one day to visit, you’ll still be able to see a lot, but having two solid days would be perfect.  We spent two and a half days in Tallinn itself which was perfect.  The remainder of our week was spent elsewhere in Estonia.

Tallinn – one-day and two-day itinerary

Whether you are looking for things to do in Tallinn in one day or two days, this guide will have you covered.  Many cruise ships come into port in Estonia, but those stopping by normally have a brief stay of a few hours.

Free walking tour in Tallinn

This free walking tour guide will allow you to pick the best things to do for your short-stay in Tallinn.

Tallinn Old Town

Ancient cobblestoned roads and laneways, meandering throughout one of the most preserved medieval cities in Europe is just the beginning.  An (almost) intact wall of defence protected this city from as far back as the 13th century.  It’s almost incredible to think that it survived two world wars and a variety of other conflicts, without being destroyed.  There are areas within the walls that suffered this fate during World War Two, so it’s not like it was out of the question.  Thankfully, it is now UNESCO protected.

There are churches and a Gothic medieval town square, not dissimilar to those we saw in Belgium.  Ornate street lamps and buildings exposing layer upon layer of different building materials,  hark back to yesteryear and remind us of the stories that this city keeps.  The Old Town is compact, a mixture of the lower and upper towns, two areas where life played out very differently for those that lived here.  A gate separated the two, with the rulers and nobility living on the upper section, a hill called Toompea, and the working class at the bottom.  Outside the walls, parkland provides a welcome patch of green space before the Old Town of Tallinn is merged with the more modern version.

Here’s our pick of the best things to do in Tallinn Old Town.  Put your comfortable shoes on conduct your own free walking tour of Tallinn.  It’s the best way and allows you to stop and take a peek into all the nooks, crannies and secret laneways you’ll uncover along the way.

The town wall

Nearly two kilometres in length, the wall is dotted with 20 huge towers as well.  Originally there were about double that amount, so it would have looked even more impressive.  At Helleman Tower, there is a portion of the wall that can be walked across to Munkadetagune Tower, providing a reasonable view over the rooftops of the old city.

Fat Margaret and the Great Coastal Gate

At the northern end of the cobbled Pikk Street, the Great Coastal Gate containing the Estonian coat of arms represented the main entry into the town.  Pikk Street was the main street for merchants, coming from the nearby port.  Here they set up trading houses from where they would buy and sell their goods.

 The Great Coastal Gate is one of only two remaining city gates, built around the perimeter as a line of defence.   Adjacent to the gate is Fat Margaret.  With a  25 metre diameter, 20 metres high, and impenetrable five metre thick walls, the name is rather unfortunate but fitting at the same time.  Used as a cannon tower, it was built centuries after the gate was built.

FAt MArgaret tower in Estonia
Fat Margaret cannon tower

Nowadays, Fat Margaret is used as a museum, although it is currently closed for renovation.  It’s a great place to start your exploration of the Old Town, winding your way up one of the major streets inside the walls.

Great Coastal Gate
Great Coastal Gate

Walking inside the gate feels like you’ve stepped into a book of fairytales.  Just inside on the right, you’ll find the Three Sisters, a 15th-century house, warehouse and office for wealthy merchants. The soft pastel coloured buildings with their triangular, gabled roofs line the streets.  Look up and you will also see the signs of this once thriving merchant street.

Under the gable roof, there remains evidence of the cranes that were once positioned here to allow for goods to be lifted up from street level.   Our feet, in our flat shoes, walk quietly over the cobbles.  The streets are quiet in the early hours and it’s just us around.  Then the silence is broken with the sound of car tyres rolling over the stones, most of which look very old.  The sound reminds me of being on the Champs-Elysées, where cars in their droves speed over the same kind of cobble.  It’s a weird association, but one my mind makes instantly.

The tallest building in Tallinn, St Olaf’s Church was also once the tallest in all of Scandinavia. Inside, it’s a very plain church, with plain white walls and high arched ceilings.  You can climb the tower of 234 steps for a small fee.

Tallinn Estonia st Olafs Church

KGB Prison Cells

As you arrive at the corner of Pikk and Pagari Street, there is a stark change to the buildings that are immediately obvious.  Glance down at street level and you will see that all the windows have been blocked up.  All around, similar apertures have decorative gates, windows and various other door coverings.  Once a humble residential building, then the central command of the Estonian War Ministry, it later became the scene of untold horror during World War Two

From 1941 and continuing well after the end of the war, until 1950, the Estonia Soviet Socialist Republic used this building as prison cells to torture people that they believed were enemies.  Whilst many of those captured were ethnic Estonian nationals, with a focus on politicians, intellectuals and bureaucrats, it didn’t take much to upset the ESSR.

….”not much was needed in order to become an enemy of the state – simply a wrong word or an awkward glance could warrant being sent to prison or shot by these organisations….” – KGB Prison Cell exhibition

KGB HQ windows

It doesn’t take long when you put your head inside one of the thick-walled cells, with blocked up windows and wire gates to imagine that there would have been some heavy punishment meted out.  Along with concrete walls half a metre thick there was no way anyone passing by would have heard a sound.  There would have been no way to know what atrocities were being carried out just metres below the surface.  Many of the prisoners were either killed following their interrogation or sent to labour camps in the heart of Siberia.

Whilst the entrance price is rather steep, it’s a sobering and interesting recount of the history of these cells, with video and other imagery assisting with understanding. It’s yet another example of atrocious historical war crimes, and it gives context to the political and cultural situation that exists in Estonia today.

kgb quote

An art exhibition by Estonian Joann Saarnitt vividly tells the story of his experience during the war years.  Seconded to the Red Army during the occupation, he saw so much.  He escaped, joined the Germany army, then was later re-captured by the Soviets before finally fleeing once more, permanently this time.  His artwork is a direct reflection of the things he saw over this period.

Great Guild Hall

All along Pikk Street are reminders of their merchant past with guild halls of varying kinds built to cater to the various associations that were created.  Up until the 19th century, German merchants were a strong force in Estonia.  The wealthy merchants were members of the Great Guild, whilst those deemed less important (usually because they weren’t wealthy enough or were unmarried) were members of the Black Heads Society.  Both had their own specific building in which to gather.  The Great Guild Hall is in a small square near the Holy Spirit Church, which has a clock dating back to 1633.

Tallinn doesn’t have one unique type of architecture but is rather a blend of different styles influences.  Hardly surprising given its history.  Apart from 20 years during the 20th century, Estonia was ruled by someone else until it achieved its independence in 1991.  There are a few beautiful examples of the art nouveau style that pop up along Pikk Street as well.

art nouveau
Art Nouveau building at 23/25 Pikk St

Town Square

The Town Square is pretty but not as engaging as I thought it would be.   Granted, there were fewer people here than would be in summer but we weren’t in the middle of winter either and there just didn’t seem to be a great vibe here.

tallin town square
Town Square

The town hall dating back to the 15th century is the most significant building on the square that was once the central market area for the lower town.

town hall
Town Hall

Harju Street

Harju Street, so named because it was once the main road leading to the city of Harjumaa, dates back to early medieval times.  Over the years it has been called the Blacksmith St, Jugmakers St and Tinners St, all referencing the types of tradespeople that worked here.  Nowadays. it’s considered part of central Tallinn and has many modern businesses here.  Much of it has been rebuilt, however, after being demolished by bombs during World War Two.

Note the damage in the image below.  In the rear of the photo, you can see several original buildings.

St Nicholas’ Church, also destroyed, was rebuilt in the 1980s and now sits impressively on the hill overlooking an area that has been left as green space.

st nicholas church
St Nicholas Church

Freedom Square

A little further down, at the end of Harju Street is Freedom Square.  Other than the huge glass cross of the War of Independence and a viewing area where you can see the Harju Gates that once protected the town on this end, it’s largely a pedestrian area and place for events.  We were unable to see the War of Independence memorial when we visited as it was fully covered and undergoing maintenance.

freedom square
Freedom Square

From Freedom Square, we began our walk up to Toompea Hill.  To the right of the War of Independence, walk along Komandandi tee and turn right at Toompea.  Alternatively, there are steps that come off Komandandi tee that will take you through the Danish King’s Garden.  Positioned near one of the high walls is the Kiek in de Kök tower, providing visibility for the military personnel who worked here.

Kiek in de Kök tower
Kiek in de Kök tower

Toompea Hill

Toompea Hill overlooks the Old Town and is a must-visit area in Tallinn for many reasons.  As the home to many embassies and government buildings, it makes for an interesting stroll.  Toompea Castle which sits proudly on the hill is the home to the Estonian Parliament.

There’s also the striking, not to be missed, Russian Orthodox cathedral.  The onion-domed St Alexander Nevsky Cathedral was built on Toompea Hill in 1900 as a defiant strategic move to note who ruled the country, during a period of rising Estonian nationalism.  It faces the country’s parliament directly across from it.

St. Alexander Nevsky Cathedral
St. Alexander Nevsky Cathedral

In contrast to the Russian architecture, the Cathedral of Saint Mary the Virgin (also known as the Dome Church)  is typically Gothic.  Whilst not an incredibly spectacular view from outside, inside it showcases the opulence of the German nobility who frequented the church.  The walls are covered with coats of arms.  Climb the tower for a good view too.

Dome Church (Cathedral of Saint Mary the Virgin)
Cathedral of Saint Mary the Virgin

We loved just walking around up here in one of the oldest parts of Tallinn.  Laneways that wove across and around the hill, exposing hidden courtyards and wonderful doors too.

Piiskopi – Bishop’s Garden

view from bishops garden

For one of the best views in Tallinn, make sure you find the Bishop’s Garden, once the gardens of the nearby Dome Church.  From up here, it’s fantastic to see so many of the city’s towers.

Because you can never have too many views, don’t miss Patkuli, another viewing area a little lower down the hill and with views towards the port.

Patkul lookout Tallinn
Patkuli lookout

Head back down the hill along Pikk Jalg, also known as the “Long Walk”.  It’s such a beautiful way to walk back down the hill, with the street lined on both sides with high stone walls.  Always in sight is the red roof of the Long Walk gate.  Behind it is the striking tower of St Olaf’s Church.

piik jalg the long walk
The Long Walk

The Short Leg Gate was the shortcut between the lower and upper town.  This gate was considered to belong to the lower town and controlled the movement of people through it.  The area around the gate was fortified, allowing the lower town to remain protected from those who invaded the upper town.  This location is still used as a poignant meeting place between the Mayor of Tallinn and the Prime Minister of Estonia whenever the situation dictates the two coming together.

Viru Gate

Back in the centre of the Old Town, cross through the Town Square and head down Viru Street. Along this busy street you’ll find some great clothes and shoe shops, alongside the souvenir shops designed to lessen the load of a tourist’s wallet.  There are some very good cafes and restaurants here and if you have a hankering for Australian beef, you’ll find a terrific restaurant here too.

To the left of Viru Street, you’ll find Müürivahe Street.  Tucked under the arches of a part of the old wall, you’ll find street vendors selling all kinds of jumpers.  In complete contrast to these homogenous jumpers, you’ll find this street is also the home of local artisans and craftspeople.  The Viru Gates represent the end of the Old Town in this area, before crossing into the Rotermann Quarter.

Viru Gates - free walking tour tallinn
Viru Gates

Other things to do in Tallinn

Look out for the hidden courtyards

Off many of the main streets, there are small laneways that often lead into amazing and colourful courtyards like the “Masters’ Courtyard” below.  In days gone by, this was where you could find craftsmen, working away.  On the day we were here, there were freelance painters sitting on the steps mirroring these medieval days, whilst others sat around an enjoyed a coffee and a chat.

Rotermann Quarter

Once a heavy industrial area, the old warehouses and mills of the Rotermann Quarter are now being replaced by modern restaurants and shops.  Located between the port and the Old Town, it’s also a burgeoning cultural precinct, particularly around Viru Square.

Kadriorg District

With a large green park as the central drawcard, the prestigious Kadriorg district makes a worthwhile area to visit.  The Kadriorg Palace and surrounding grounds were once the summer home of Russian Czar Peter the Great.  With wooden houses dating back to the 1920s, having an address here is highly sought after.

Getting to Kadriorg is easiest by tram or bus.

Telliskivi Creative City

Continuing the leading edge activities that occur in Tallinn, Telliskivi Creative City is the place where plenty of hipsters can be found.  There’s street art, cool cafes and craft beer.  There are designer studios, cultural events that take place during the year, and shops selling unique designer wares.  What’s not to like?

Balti Jaama Market

In the Telliskivi area, just outside the Old Town is a wonderful old market selling great fresh produce and street food.


Grab a hot drink and tasty pastry at Maiasmokk, the oldest cafe in Tallinn.  Located along Pikk Street, it’s opulent inside with plenty of old world charm.  It’s also known for painted marzipan treats, something we are not fond of but they are worth having a look at them in the co-located sweet shop.

Maiasmokk cafe - guide to visiting tallin in 1 day
Maiasmokk morning tea

Day trips from Tallinn

Tallinn is a terrific place to stay for a few days and in fact, I highly recommend this. It also provides an excellent opportunity to use as a base for day trips into the Estonian countryside.  Tallinn is not a singular representative of Estonia overall.  Rather, the landscape of both the natural and built environments vary widely from the city to the east and west coast.  Soviet influences become more obvious as you approach the Russian border.  The eastern areas are more European.

Haapsalu, Narva, Parnu and Tartu are the main cities where day trips would be a good idea as well as the Lahemaa National Park.  Offshore, Helsinki is one of the most popular day trips from Tallinn.

We did day trips to Haapsalu, Narva and the Lahemaa National Park.

Tips for making the most of a visit to Tallinn

  • Go in different seasons if you are able.  In summer, like a northern European city, it’s a vibrant place to be.  The weather is great, there are plenty of people about and everything is open.  Some cities like the seaside towns of Haapsalu and Parnu really come alive during this season.  The downside, of course, is the crowds of tourists.
  • For a different and much quieter perspective, go in the autumn.  The streets can almost feel like your own, especially in the early morning, and the hordes of tourists just don’t exist.
  • If you can, do your research and find out when the cruise ships are in port and then visit on another day.  The cruise ships bring throngs of people into the city all at once, making it extremely busy, and in my opinion, less authentic.
  • Check out as many of the great food places as you can.  Tallinn is becoming widely regarded as a location for high-quality, innovative food.  A great restaurant experience can be found for a fraction of the price you might pay in other European cities.
  • Make a reservation!  The restaurants are popular, even in the offseason, so to avoid disappointment, be sure to make a booking.
  • Walk around as much as you can.  Tallinn is a very easy city to walk around and doing so ensures you don’t miss a thing.
  • Wear comfortable shoes.  Once you’ve walked around on the cobbled streets all day, or navigated the streets in the wet or snow, you’ll be thankful you did.
  • Stay in the Old Town or just outside it.  Whilst it’s easy enough to get public transport into the Old Town, staying within the walls is the perfect place to stay.
  • Keep an eye on your weather app for the “feels like” temperature before heading outdoors.  In autumn and winter, you’ll be grateful as the apparent temperature can be considerably lower to the reported temperatures.
  • You don’t really need cash.  Of course, if cash is your thing, then have a supply of Euro’s on hand but Estonia is a tech-savvy country and credit cards are used everywhere.  We didn’t use cash at all in the week we were there.
  • We didn’t find Estonia expensive, and in fact, there were many things we considered to be quite cheap.  But, we come from Australia where we are used to a high cost of living.  Other visitors who aren’t may well find it expensive, similar to other Scandinavian countries.  Many Finnish people travel to Estonia because they believe it is cheaper than home for some items.
  • If you are entering Tallinn from the port, don’t just walk into the first restaurant you see. Pikk Street, which is the main entry into town from the port is lined with restaurants for the tourist market.  You’ll recognise them easily. They’ll have someone out the front with a stack of menus, calling at you to come inside, or they will have big signs in the windows with photos of food and lots of English flags.  There are some great restaurants in this area too, you just need to look further afield.

For those that know a little about Tallinn, you’ll most likely recognise that I haven’t mentioned the themed medieval restaurants.  This is quite deliberate as we believe there are so many better places to eat in Tallinn, serving better food at better prices and without all the hype.  Many will not agree I’m sure, but I think this is one of the things to do in Tallinn that is over-rated and most definitely over-priced.

Being tourist restaurants, the food quality is also not going to hit any peaks.  If you aren’t really looking for the best food options in Tallinn, and the theatre of the medieval days intrigues you, then by all means, you should do it.  Just understand that they are more tourist attraction than great dining experiences.

Where is Tallinn?

Tallinn, the capital of Estonia, is located in northern Europe.  It is bordered by Latvia to the south and Russia to the east.  To the north is the Gulf of Finland.

How to get to Tallinn

By air

Tallinn is serviced by Lennart Meri Tallinn Airport and is only four kilometres from the city.  A variety of mainstream domestic and international air carriers operate from here.

Bus number 2 and tram number 4 operate to the city centre.  We found using Uber was just as easy and inexpensive.  Taxis are also available.

Book a flight

By ferry

Ferries can be used to get to Tallinn from Helsinki and Stockholm.  A cruise ship also arrives weekly from St Petersburg.  Cruise ships also make a stopover in Tallinn part of their itinerary.

Depending on the ferry taken, the trip to and from Helsinki is two to three hours one way.  From Stockholm, it’s often around 15 hours and travels through the night.

It’s an easy walk, approximately 15 minutes from the port into the Old Town.  Taxis and Uber also operate from the port.

Book a ferry

By bus and train

Several bus lines operate from a couple of nearby European cities and a train operates from Moscow.

Book a train

By car

Major highways connect Estonia and vehicles may also be brought into the country aboard the ferries.

Book a hire car

Where to stay in Tallinn

Staying in the Old Town in Tallinn is highly recommended.  Having discovered the Masters’ Courtyard whilst we were in Tallinn, I would have loved to have stayed in the Villa Hortensia apartments located right in the courtyard.

View the photos, prices and reviews on Trip Advisor.

The Three Sisters, located in the merchant building at the beginning of Pikk Street is at the luxury end of accommodation in Tallinn.

View the photos, prices and reviews on Trip Advisor.

A more modern building, but still 19th century, the Hotel Telegraaf also provides a top-end comfortable stay in the Old Town.

View the prices, photos and reviews on Trip Advisor.

We stayed in an apartment just outside of the Old Town, with an incredible view of the wall and the St Olaf Church.

Apartment Tallin
Our apartment in Tallinn

Beer and Croissants was a guest of Visit Estonia as part of their tourism initiative, Storyteller’s Nest.  As always, all editorial content, images and opinions are entirely our own.

1 thought on “Free walking tour in Tallinn: A guide for first time visitors to Tallinn Estonia”

  1. Thank you for a wonderful overview of Tallin with spectacular photographs and excellent information. I shall be there in the last week of September, probably lovely weather, being Autumn.
    Regards, KF

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