48 hours in Tallinn, Estonia for an awesome trip

by Charlie - Where Charlie Wanders
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If you are looking for a perfect city break for a long weekend, Tallinn is the one! 48 hours in Tallinn is the ideal amount of time to spend. It is a small city, so you can pack in the highlights and get a feel of the city without needing to take too much leave or feel like you are rushing around. It is the perfect size for walking around and getting your steps up but without anything feeling like it is too far.

image of the Town Square in Tallinn.

What to make it a longer break? It’s also the perfect city to combine with other capitals for a tour of the Baltics. Or, you can even get the ferry over to Helsinki to explore some of Finland: 9 Marvellous things to do in Helsinki, Finland

Day 1 – 48 hours in Tallinn

A free walking tour – to start 48 hours in Tallinn

The best way to begin 48 hours in Tallinn? Or indeed in any city? With a free walking tour. It is the best way to get a feel of a place, understand the key moments in its history, begin to navigate your way around and work out the highlights you want to see.

Tallinn is no exception. Esta Adventures has a Tallinn in a nutshell tour, which covers all the most important sights in Tallinn’s Old Town and will take you through the fascinating history from medieval times, through the Soviet period and to modern Estonia. There are daily tours at both 11 am and 4 pm.

View the city from above

After the walking tour, you might want to go back and visit some of the sites for a little longer. Just to make sure you have got that photo. Two of the best views of the city are Kohtuotsa Viewing Platform and the Patkuli Viewing Platform.

The Kohtuotsa platform also has the famous ‘The Times We Had’ mural painted on a wall to the left, so worth more than just the view! This special part of Tallinn overlooks the signature red roofs, as well as the high-rise buildings in the newest part of the city.

Patkuli is just around the corner, literally a 1 minute walk so incredibly easy to see both. This beautiful vantage point gives you a clear look at the fairytale side of Tallinn. You’ll find city walls, towers with peak rooftops, a view of St Olaf’s church, and the harbour area below.

Kohtuotsa | Kohtu 12, 10130 Tallinn | Map / Patkuli | Rahukohtu 5, 10130 Tallinn | Map

Explore the upper town – 48 hours in Tallinn

Because you are at these viewpoints, it means you’re already in the Upper Town (called Toompea). So this is the perfect moment to take some time to explore. Start by just wandering around and viewing the beautiful buildings and architecture. This is where the rich merchants used to live so a lot of the buildings are very grand and are today the location of embassies and government buildings. One of the most impressive buildings in this area is the stunning Alexander Nevsky Cathedral – this Russian Orthodox Church is free to go inside.

Find the Town Square – 48 hours in Tallinn

After you have had your fill of the upper town, meander your way down the hill towards the Old Town. The streets are tiny and winding, so it can feel like you can get lost easily, but they all lead to the Town Square or Tallinna Raekoja Plats, so this is a really good place to start. Located right in the middle of the Old Town is the marketplace and centre of the Lower Town, and has been here since the 13th century. Meaning it has been the heart of the city life for over eight centuries.

While you are here, you can see some of the most impressive medieval architecture, and get a feel of what the city has been like through the ages. In the winter this is also the location of a beautiful Christmas market. It’s packed with restaurants and cafes, and a great place to start exploring the Old Town.

The oldest pharmacy

While you are in the Town Square make sure to stop by Raeapteek. This is the oldest pharmacy in Europe that has been continually operating from the same premises; first mentioned in records in 1422! It might seem odd to suggest visiting a pharmacy on a city break itinerary, but it is so interesting and well worth a visit. It is very traditional inside. You will also find a museum next to the pharmacy. Here you can learn about the history and medieval healing methods.

Wander the Old Town

You’ve seen the beautiful viewing platforms and found the Town Square, so now it’s time to wander the rest of the Old Town. It is one of Europe’s best-preserved historical city centres, and you will feel like you have stepped into a fairy tale packed full of cobbled streets and medieval architecture. You could spend hours just exploring all the beautiful streets.

Viru Gate

Viru Gate is a pair of towers dating back from the 14th century and was originally part of the defence system that guarded the city. Originally there were 45 towers in the old stone walls that protected the city, and these two are some of the best preserved. They formed a gate that was one of the main entrances into the Old Town. However, they are only a fraction of the original structure of the gate. Originally there was a larger gate which was built a little further in and was held up by a set of square towers. Most of the gate was pulled down in 1880. Now it is an iconic photo spot in Tallinn.

image of the two towers of Viru Gate at the entrance to the old town of Tallinn

Walk the city walls

As mentioned originally Tallinn’s Old Town was once enclosed by a long stone wall, This was 2.5 km long and split up by 45 towers. Large sections remain, including 26 of the original towers, which help to give Tallinn its fairy-tale feel. There are some of these sections which you can head up and walk along. Head to the Hellemann Tower, where there is a 200-metre-long section of the wall that connects with Munkadetagune Tower.

Climb up the steep stairs and you will arrive at the attic, which opens up as a viewing platform. You can then walk out on the wall and look out over a view of the city of Tallinn. Again, it feels like it’s right out of a medieval story, so it is well worth a visit.

Dinner at Rataskaevu 16

After a busy day of exploring, you will want to treat yourself to a delicious dinner. And Rataskaevu 16 is just the place! Delicious food, with a warm atmosphere and great service. The food is exciting, and beautiful and has a really good selection for all dietaries. Make sure to ask about the ghost stories related to this address. And while in the loo, look down to see a glass panel showing the old cellars.

Day 2 – 48 hours in Tallinn

Telliskivi Creative City

Start day 2 of your 48 hours in Tallinn with a completely different vibe to the historical, fairytale vibes of the Old Town. Head to the Telliskivi Creative City. It’s about a 20-minute walk from the Old Town, or there are plenty of tram stops nearby. Located in the old industrial complex of Tallinn, and is home to boutique shops, quirky cafes, galleries, various creative companies, start-ups, and restaurants. There is also plenty of cool street art to find.

Spend the morning there and take the time to explore all the little areas, and relax with a coffee and some lunch.

Learn about the KGB history in Estonia

After lunch head back to the older part of the city and learn about some of the darker side of Tallinn’s history. The KGB Prison Cells are former prison cells which were used by the KGB during the Soviet Occupation. It’s not going to be the cheeriest afternoon, but important to see all sides of the city.

The unassuming facade hides a dark past, and once you enter you head down into the basement. Here are the 18 cells which held prisoners while they were interrogated. It is informative, interesting and heartbreaking. But the information is exhibited in a really important way. Above the basement, the building is now residential.

St Catherine’s Passage

For an interesting photo stop, make sure to pop by St Catherine’s passage. Formally known as Monk’s Alley, it winds from Vene Street past the southern end of the Dominican monastery to Müürivahe Street. It now gets its name from the nearby St Catherine’s church and is thought to have been built around 700 years ago.

image of a woman standing under the arches of St Catherine's Passage in Tallinn

The southern side of the alley is lined with buildings that are mainly from the 15th to 17th century. The alley as a whole retains its medieval charm and was last restored in 1995. Here you can also find handicraft workshops and you can watch the artists at work creating things like ceramics, hats and glass. It also makes for a really pretty picture!

Tallinn’s Oldest Cafe

After an intense afternoon of sightseeing, treat yourself to a delicious chai latte and a huge selection of sweet treats at Tallinn’s oldest cafe. Its current form dates back to 1864, making it the oldest operational café in Estonia. The premises also contain a museum about the history and uses of marzipan. Its beautiful interior makes it the perfect place to relax. Indeed the first floor decor hasn’t been changed in over 100 years.

Drinks at Olde Haus

The perfect way to round off your 48 hours in Tallinn? By celebrating with a beer of course! This is the most authentic medieval dining experience in the world. Everything is lit by candlelight, the beer is served in tankards and even the toilet is candlelit. It’s fun, if not a little gimmicky although the traditions and history of the building and the sheer passion that the staff and owners have for them is something else. It’s like the best interactive museum, it does have a beer after all! And the building itself is genuine, parts of it date back to the 14th Century.

The beer itself is not just regular beer but a huge choice of traditional brews, from Dark Honey to Light Cinnamon beer and
Light Ginger beer. There are also schnapps, which are strong but essential. Try the pepper schnapps, which have healing drops of pepper. The food menu is equally interesting, with a lot of choices of game meets. If you want to try elk, oxen, bear or boar – this is the place.

48 hours in Tallinn – the round-up

Hopefully, this post helps you plan your trip to the city and gives you plenty of ideas on how to spend 48 hours in Tallinn. 2 days is the perfect amount of time to spend in this charming city. If you are planning a trip I’d love to hear from you.


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image of how to spend 48 hours in Tallinn infographic
image of how to spend 48 hours in Tallinn infographic

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