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The Perfect City Break in Tallinn – Make the Most of Tallinn in 2 Days

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If you only have one weekend to dash to The Baltics, may we humbly suggest that you choose to spend your time in Tallinn. This fairytale capital is full of history and around every corner, you will find a little spot that is utterly enchanting. So, how can you make the most of Tallinn in 2 days? What can you cram in, what should you see and what should you eat? This is your itinerary for the perfect city break in Tallinn.

A Bit About Tallinn

Tallinn is the diminutive capital city of Estonia. The city is home to around 427,000 residents. It’s the northernmost Baltic states capital, sitting right on the north coast with waters of the Gulf of Finland beyond. There has been a settlement here for around 2100 years and it was properly fortified in the 1400s. A surprising amount of the walls and fortifications still remain…but more on that later. Walking through the old town, you could be mistaken for thinking you are on a film set or Medieval Land at Disney but these are genuinely ancient buildings that are lovingly preserved and maintained. In fact, it is a UNESCO World Heritage Site so it will be preserved for future generations too.

All About the Tallinn Card

First things first, get yourself a Tallinn Card. There are plenty of city card schemes around the world, and I am usually not a huge fan, but the value of the Tallinn Card is almost unrivalled. Cards get 24/48/72 hours of public transport. This includes the tram to and from the airport which takes no time at all. As well as this, there are over 50 attractions that are included. When you are on a tight schedule, it’s so nice to quickly pop in a museum or a church, have a whizz around and leave again without the “Well, I’ve paid for it so now I must read every word” feeling. If the place you have entered interests you, stay. If not, move on to the next. The card also gets discounts at other museums and restaurants and includes Hop On, Hop Off buses that run at the weekends. At (€35 for 24 hours, €52 for 48 hours and for 72 hours, I believe it is impressive value for money and will really improve your city break in Tallinn.

The Perfect City Break in Tallinn – Make the Most of Tallinn in 2 Days

DAY ONE

Get your steps in and culture on with this wonderful walk around Tallinn.

Start at Freedom Square

We start at the square that was the heart of the independence movement in the early days of Estonia. Throughout the Soviet period, it was left to deteriorate but when Estonia once again reclaimed its independence in the 1990s, the space was renovated and is now a modern spot with a couple of cool spots for a drink.

Some things to look out for:

  • St John’s Church – A pretty yellow neo-gothic Lutheran church that dates from the late 1860s (practically new in this medieval city).
  • War of Independence Victory Column – This striking glass-lined cross was built in 2009 to commemorate the 4000 people lost in the Estonian War of Independence (1918-1920). Construction was planned in the 1930s but the Soviets delayed the plans by 60-ish years.
  • Harju Gate Tower – Look out for a big stone rectangle in the corner of the square. Below the glass, you can see the remains of an old city gate. Mind you, there are plenty of gates that are still intact o don’t linger for too long.
  • The Chopin Bench – This cool present from the Polish embassy plays two popular Chopin pieces. Poland and was unveiled on what would have been the composer’s 200th birthday.

No Giggling at Kiek in de Kök Museum

I know, I know, if you are giggling at that name don’t worry, I did too. However, it is actually an old german phrase meaning Peep into the Kitchen. It refers to the ability of the tower’s occupants to see into the kitchens of the houses around. This squat stone tower, built in 1497, is one of four that combined with some cool tunnels, make up the museum. There is a carved stone museum in one part and a permanent exhibition about Tallinn’s military history, as well as changing exhibitions.

Entrance to Kiek in de Kök and the Bastion Tunnels are included with the Tallinn Card.

Pretty in Pink – Toompea Castle

Stop off and climb Linda Hill for a great view across to the oldest parts of Toompea Castle. The striking 13th-century Tall Herman tower makes a lovely contrast to the baroque pink palace it protects. The main pink building you can see here was built in the 1700s by the Russians.

In the opposite direction, you will see the gorgeous Linda Monument (hence the name of the park). Linda, was said to be the wife of Kalev, who founded the city of Tallinn. The statue depicts her sadly looking down as she mourns his passing. She became a symbol for people exiled to Siberia during Soviet rule so coming here to lay flowers became an act of sedition.

Walk around the edge of the pink Toompea Castle and you will come to the entrance. It is such a beautiful building and inside it houses a building from the 1920s, designed to house the parliament of Estonia (Riigikogu). It is actually possible to go around on a free guided tour but the English tour is only at 11:00 on Fridays and you need to bring a valid ID.

Admire the Icons at Alexander Nevsky Cathedral

Directly opposite is the arresting Russian Orthodox Alexander Nevsky Cathedral. The cathedral is multi-onion-domed, decorated with Russian Revival flourishes and stands high above the surrounding buildings. Construction ended on the Cathedral in 1900s, when Estonia was still part of the Russian Empire. it was almost destroyed when Estonia took independence in the 1920s but luckily, it survived as was reinstated as a church when the Soviets left. If you are around just before a service, you will get to hear the 11 bells housed within those gorgeous domes. If it is not service time, you can head inside for free. Through the heady incense-filled air, golden paintings glint on the icon screen and the tiled floor clicks as worshippers move between prayers.

Wooden Wonders at St Mary’s Cathedral

Just a two-minute walk away, up Toompea hill, is a completely different kind of cathedral. It used to be made of wood, in fact, it was repeatedly made of wood but as these things tend to do, it kept burning down. It was finally made of stone in the 1400s…but then much of the interior was ruined in a fire. What you see now is mostly from the 1600s. Around the walls, there are beautiful timber coats of arms belonging to the Tallinn nobility, dating from the 17th to the 20th century. As well as these smaller wooden details, you will see a huge wooden pulpit and altar. They are quite remarkable and all the work of one carpenter. Finally, there is a big wooden section that looks like a private theatre box. it is unusual but you could easily imagine the richest worshippers in town having these VIP seats.

The tower, added in the 1700s, was closed during our visit but is due to reopen in autumn 2022. It is an excellent viewpoint.

Entrance is included with the Tallinn card.

Take in the View Over the Red Roofs of Tallinn

As you wind your way through the ancient lanes of Toompea, you will find two brilliant places to enjoy the view across Tallinn.

  • Patkuli Viewing Platform – There are a whole lot of steps to reach this viewing platform if you come from the other direction but approaching from the shallow slope of the hill, as we have, makes the height quite a pleasing surprise. Once you pass through the archway you will find an information board and a 180-degree view over the railings. There are a couple of free-to-use binocular stands which is a cute touch. See how many spires you can count.
  • Kohtuotsa Viewpoint – A little more rough and tumble, this spot has a wall which is great to perch upon for a snap. From here you can see both the old city roofs, covered in gorgeous red tiles, the newer tall, glass buildings and, in the distance. Soviet housing blocks.
Kohtuotsa Viewpoint
The Danish King’s Garden

Throughout this stone-walled terrace dementor-like figures of monks bow their heads in eerie grey stone. They were a cool contrast to the bright flowers during a bright summer day but I am sure they are super creepy in the depths of winter. There is a nice view from here too but the main sight, St Nicolas church, was covered in scaffolding so I didn’t take a photo.

It is said that the flag of Denmark was discovered/created here and so they celebrate the Day of the Danish flag on 15th June every year. The King of Denmark invaded Tallinn, and just when he thought it was a done deal, the troops were ambushed by the local forces. He collapsed in despair and (as legend has it) a red scrap of material with a white cross fell from the sky and he rather liked it.

Head through up the stairs through the Short Leg Gate Tower or down the stairs from here and wander down the seriously picturesque Pikk Jalg. It is the oldest street in the city and is made of huge cobblestones. Pikk Jalg means Long Leg or Long Boot. Don’t you just love the names in Tallinn?! The slope is a little steep but there is a smooth section on the right hand side with a handrail if you have shoes or knees that don’t enjoy cobbles.

Grab a Snack at Loiri Pagar

There are baked goods galore in this hidden gem. Black bread, sweet treats, soft pretzels and savoury pies are all on offer, ad at a fantastic price! If you need a caffeine fix, this is a great place to grab a coffee too. It is much cheaper than the touristy spots up the hill or further into the Old Town. There is a small spot to eat but if it is sunny, you would be better off taking your bits and bobs away and taking a seat in the verdant parks nearby.

Wander the Walls at Nunnatorn ja Linnamüüri

Up a steep spiral staircase, is a wonderful section of the medieval wall that you can explore. There is almost 2 km of wall left, and 20 towers but this is the best section. You can work your way between three towers (Nunna, Sauna & Kuldjala), take in some views and enjoy the novelty of walking on a wall that is around 700 years old!

Entrance is free with Tallinn Card.

Backtrack to Long Leg Gate at the bottom of Pikk Jalg and its just a two minute walk to the immense Town Hall Square.

Take it All in at Town Hall Square

The Old Town Hall

Dominating the south side of the square is the HUGE Old Town hall which turned 700 in 2022. It was first mentioned in 1322 but it was rebuilt in its current form 100 years later. It is a whopping 36.8 m / 121 ft long and must have been overwhelming to a medieval populus. The building has been through ongoing renovations but every effort is undertaken to preserve it. In 19th century renovation, they found a cache of city documents that spanned 500 years from 1200-1700. City administration only moved out in the 1970s! It is still used for ceremonial purposes.

it is possible to visit from July to August and entrance is free with the Tallinn card. This does not include entrance to the tower. You can climb 34m (about 60% of the way up the tower) for free with the Tallinn Card but it is priced seperately for ad hoc visitors.

Pick up a Potion…or a Plaster at the Town Hall Pharmacy

You might have seen an old pharmacy in Dubrovnik but this is only the third oldest in the world. There are those that claim the Esteva pharmacy in Spain is the oldest, or a few in Italy BUT for the oldest working pharmacy that is still in its original spot, you have to visit Raeapteek in Tallinn. This shop has been here since at least 1422. Now, at home, I favour a Boots because I just gotta get those Advantage Points but if I were to fall ill or need some extra toiletries during my trip to Tallinn, I would make sure to come here. As well as picking up a few medicines you can visit the museum next door. This guides visitors through the weird and wonderful world of old methods of treating the sick. It’s free for groups under 10 people but if you are a large group they will charge €2 each. They also offer special guided tours that include a Claret tasting, herbal tea tasting, marzipan workshop or a combination of all of those.

Indulge your Sweet Tooth at Kehrwieder Saiakang Chocolaterie

Is it possible to walk past a chocolate cafe and not grab something delicious? What about if they also roast their own incredible coffee? Still not convinced? What if I told you they have a gorgeous black cafe cat? Well, it is DEFINITELY worth stopping at Kehrwieder Saiakang Chocolaterie for something delicious. How about a gorgeous cup of caffeine and a belly scratch (for the cat, not for you). We had a super light but decadent white chocolate and berry cheesecake and a real chocolate mocha to share. It was a chocoholic’s dream without being too sweet.

Tallinn Card holders get an extra little sweet treat for free.

Pass Through St Catherine’s Passage

St Catherine’s Passage used to be called Monk’s Passage and I suppose it had an equal claim to both names as it runs past both St Catherine’s Church and the old Dominican Monastery. The alley was restored in the 1990s and is home to fewer monks and more cute artists’ workshops. It is thoroughly charming. Look out for the two large tombstones.

Go Back in Time for Dinner at Olde Hansa

Olde Hansa is by far the most fun restaurant in Tallinn. Usually, the idea of heading to a medieval-themed restaurant conjures up ideas of weak beer, dry chunks of meat and an overall cringe-worthy experience. There are no cringes at Olde Hansa. The menu has been created with care and there are some spectacular and intriguing drinks made on site.

The Olde Hansa building is a genuinely ancient building, with some parts dating back hundreds of years. If you ask to take a tour, you will get to see the oldest parts of the building. The interiors are decorated with murals of medieval scenes and if you look carefully, you will see the faces of the staff integrated. Its so cool.

The food is mostly based on a tasty piece of meat or fish and plenty of tasty veggies. We particularly recommend picking anything with the incredible smoked sauerkraut, it is so very delicious (and great for gut health). If you are interested in trying game meats or local seafood, you will find something to tickle your fancy. Everything has nice pickles, jams or sauces on the side too. Never fear, if you are vegetarian, there is a small vegetarian menu too called “From the Merchant’s Herb Garden” There is also the chance to try 17 things for €48 per person so if you can’t choose, let them bring you the best of what they have to offer.

Don’t skip on the drinks menu, it is full of things you won’t have tried and won’t get the chance to try again. They make a selection of schnapps in the kitchen including the unbelievably flavoursome pepper schnapps and sweeter Monks’ Bride which is packed with sweet, herbal tastes. Finally, the strengthened coffee is an excellent end to the meal, spiked with booze and topped with plenty of whipped cream.

Sip Some Mind-Bending Cocktails at Sigmund Freud Bar

Sigmund Freud bar has a menu full of unusual and exciting cocktails that we have never seen anywhere else all served in a trendy but cosy setting. When you arrive pick up a menu straight away because it takes a while to read through it, rather than scanning the standard offering. During our visit, I opted for a Stick & Carrot. This vodka, butterscotch, carrot, condensed milk and cinnamon concoction was like the best milkshake I’ve ever had. It was strangely comforting with the bitter-sweet butterscotch and warming cinnamon. it had dehydrated carrot on the top too….so good. Mr Fluskey chose a Tiki Tok. This had a first sip packed with tropical fruits but then the spiced rum came through and finally there was a bubble gum after taste. So weird, so yummy and so more-ish.

We only had time for one round when we visited and it was a real wrench to leave. that is why it is best to go after dinner rather than before (like we did).

DAY TWO

Land, Sea and Sky at Seaplane Harbour

Hop on tram 73 from the Old Town to Kalamaja for this morning’s activity.

Tallinn’s Seaplane Harbour (included with the Tallinn Card) is unlike anything else in town. It is a huge museum dedicated to warfare above, on and under the ocean. The museum is housed in a HUGE hangar and lit like a theatre set. Some say it looks like a Bond Villain’s lair and with the large British, Lembit submarine suspended in there, I have to agree. This interactive museum has enough to play with to keep younger (and young at heart) visitors occupied for a good few hours. You can pretend to fly a plane or shoot down other planes. Even cooler, you can climb aboard the submarine and explore it. There is a wonderful section on the lower floor all about a military manoeuvre in WWII that we had never heard of. it is fascinating and worth the short trip out of town.

Refuel at Reval Cafe, Vene 1

Get back on the 73 to Vabaduse väljak and it is just a four-minute walk to our lunch stop.

Reval Cafes are found throughout Tallinn and they are a real favourite with everyone from tourists who need to fuel up, to people on business lunch meetings, here for coffee and wifi, and locals who are here to chill out and enjoy their favourite dish. On the menu, you will find plenty of cafe classics and local favourites like borscht, as well as more unusual dishes like lamb dumplings with sour cream, and rice noodles with south-east Asian flavours. Best of all, the prices are very reasonable.

Oh, and they make lovely coffee and a KILLER chai latte.

Wear Your Sunglasses for the Holy Spirit Church

The brilliant white walls of the püha vaimu kogudus are blinding in the bright sunlight. You will need to look at them though to see the beautiful blue and gold clock that still keeps time despite being put here in 1684. The church itself is even older so heading inside you will see an altarpiece that is 700 years old and some gorgeous wood carvings. Entrance is free with the Tallinn card but there are concerts nearly every evening at 18:00 so you could pay for one of those to see inside and listen to some music.

House of the Blackheads

If you have ever visited Riga, you may have heard of the Blackheads. This ancient brotherhood was set up in 1399 by rich merchants that operated around Estonia and Latvia. Their patron Saint was St Mauritius, he was African and that is where the Blackheads moniker came from. These young men were not allowed to get married and would leave all their money to the group. However, in the meantime, they had some incredible parties. You can tell from the door of the building that they had some real style but you really have to head inside to see their ballrooms and other communal spaces. There were renovations in the 15th, 16th and 17th centuries but it is still the original building (not a recreation like the one in Riga). Entrance is only available with the Tallinn Card and is free.

Discover the Dark History of Tallinn at the Former KGB Headquarters

After so much ancient history, it is time to discover a much more recent slice of history. The KGB, the secret police service that operated throughout the USSR was in charge of dealing with traitors to the state, subversives and undesirables. Their interrogation techniques could go from a normal interview to genuine torture. Behind these closed doors, people were squirrelled away and often forced into questionable confessions or to turn informer to save themselves. From the outside, you can spot the bricked-up windows at street level which were to keep the sounds in and prying eyes out. Visitors can see the offices of the KGB officers, and the basement cells of those who were incarcerated here. Learn the stories of inmates in the nine years the building was used. Entrance is included on the Tallinn Card.

Admire Fat Margaret

No judgement, but this squat cannon tower from the 16th century really is a bit chubby. Apparently, the name doesn’t come from the tower itself but a plump resident. Some people say it was a wide cannon, some the chef. It houses one-half of the maritime museum (the rest is the Seaplane Harbour that you saw earlier). In this half, there is a huge collection of ship models, and some fun interactive exhibits tracing Estonia’s maritime history from the 1400s to now. Entrance is free with the Tallinn card.

Outside, on a small hill is a monument called the “Broken Line”. It commemorates those lost in a ferry disaster in the 1994 in which 852 people perished. It is very poignant whether you’ve heard of it before or not.

Test Your Thighs at St Olaf’s Church

As vivadly white as its Frozen namesake, St Olaf’s Church stands proud above Lai. The Lutheran church has a very plain interior but that isn’t really the reason we are here. It is all about the tower! The climb to the top of St Olaf’s tower is not be untaken litely. It’s a steep spiral staircase and it will make your thighs burn but trust me, the 360 views are so worth it!

On the way up, there is one place with some flip down eas to sit and get your breath back. This is a great idea! The last stretch is up a wooden staircase located in the same area as the giant bells. You then emerge onto the edge of the steeple. Don’t worry, you are fenced in. The viewing platform wraps around the whole tower and the views are amazing! You can see the whole of Tallinn, out to sea in one direction, across the old town in the other.

The church is free but the tower costs extra unless you have a Tallinn Card.

After all those steps, you have really earned your dinner…and boy, is this dinner worth it.

The Scottish Garden

Along Uus, you will find a few steps that lead you up and behind the Scottish Club. Here there is a gorgeous garden with the most unexpected of statues for a Baltic spot. The busts of notable Scottish scientists, poets and actors are dotted throughout. Remarkably, there is a strong Scottish connection here in Tallinn with big Burns Night celebrations and ceilidhs aplenty.

Keep walking through the garden for your dinner.

Taste Tallinn’s Finest food at Lee Restoran

Lee Restoran is one of those rare things, an incredible restaurant that is perfect for special group meals, intimate dates and for any adventurous foodies who want something delicious to eat. Lee is an old word for communal health so it makes sense that the atmosphere is both refined and comfortable. The tasting menu is only €55 which is a great price considering the quality of the dishes on offer. They used to focus on local produce only but decided to widen the scope and incorporate Japanese flavours whilst still championing the local fare. It has a spot in the brand new Estonian Michelin Guide and we can see why.

We were so lucky to try the full range of starters and each one was a delightful exploration of flavours. The carrot tartare was a veggie revelation, both more delicious and more sustainable than the beef it replaced. Our braised quail was wrapped in a delicate tofu skin like the most exciting giant gyoza ever. We tried the best asparagus dish I’ve ever had, perfectly crisp and covered in pike perch roe, crispy tempura nibbleys and pretty edible flowers. With every dish, we were amazed at the intriguing combinations and skill of the cookery.

The only thing I wasn’t that enamoured with was the dessert. We tried kohuke which is a traditional curd cheese (quark) dessert. It was served with rhubarb, celery and blueberries so it had a mildly sour profile. We also had some sort of rice pudding, and I hate rice pudding so that was never going to win me over. However, Mr Fluskey loved them both and finished the lot. I think I was hoping for something a little sweeter or dripping with chocolate, but that doesn’t seem to be their style.

There is also an extensive wine list including a divine sparkling wine that was an excellent start to the meal. We also tried horseradish vodka. I don’t think we really read the menu, thinking it would be an interesting shot. Turns out it was a 100ml carafe and luckily, it was surprisingly delicious. I also had a great cider and a lovely glass of rose. It was a good night!

Final Thoughts for Your City Break in Tallinn

Tallinn is absolutely dripping with history. Just walking through the streets, you feel like you are in another world and there will be a princess emerging from a medieval alley any minute. Church spires, ancient towers and cobbled streets can’t fail to whisk you to another time. However, I hope this Tallinn in 2 days itinerary has also incorporated some more recent history and some thoroughly modern food and drink options along with the more traditional fare. Book a flight, buy a Tallinn Card and hit the streets with a sense of wonder for your amazing city break in Tallinn.

Rosie xx


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