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Eye-catching Sights in Tallinn Old Town, Estonia

Forget the map in Tallinn Old Town.

Dating back at least 1,000 years, the Estonian capital’s well-preserved Old Town is a jumble of cobblestone alleys, squares buzzing with cafes and bars, attractive shops, medieval merchant houses and churches crowned with tall Gothic spires.

Like so many wonderful old towns in Europe, the Old Town of Tallin is perfect for soaking up its years of history by strolling aimlessly – and letting your curiosity guide your feet.

Tallinn Old Town, Estonia

Tallinn Old Town has a 1,000-year-old history

Designated a UNESCO World Heritage Site, the historic Old Town of Tallinn is divided into two sections – Toompea Hill (upper town) and the lower town.

We started our walking tour of Tallinn Old Town in Toompea Hill.

But it doesn’t really matter where you start.

Tallin Old Town

Two narrow, steep streets – the “Long Leg” (used by horses in days gone by) and the “Short Leg” (an alley with stairs for people) connect Toompea with the Lower Town.

Tallinn is also small enough that you won’t get too lost. (If you do, just ask a local to point you in the direction you want to go.)

Red roofs of Tallinn Old Town

Pictures of Tallinn Old Town

Okay, let’s go on a photographic walking tour of Tallinn!

1) Toompea Castle

Toompea Castle, Tallinn Old Town

Perched on top of Toompea Hill, the tower of Toompea Castle flies the blue, black and white flag of Estonia.

Toompea Castle dates back to the 1200s, but the pink Baroque-style palace is an 18th century add-on built by the Russians.

Today, Toompea Castle is home to Estonia’s parliament.

2) Alexander Nevsky Cathedral

The splendid, onion-domed Alexander Nevsky Cathedral faces Toompea Castle.

We were told most Estonians don’t really like the cathedral, as it was built in 1900 at a time when Estonia was part of the Russian Empire. But it’s beautiful to look at.

And in true Russian Orthodox style, it’s richly decorated inside with mosaics and icons.

Alexander Nevsky Cathedral Tallin

3) Eye-catching oddities and decorations

When sightseeing in Tallinn, you never know what you’ll see by looking up!

Be sure to look out for the drain pipe shaped like a large cowboy boot, complete with spurs.

Tallinn Old Town drainpipe shaped like a boot

And don’t overlook the wrought-iron street lamps and gates.

Tallinn Old Town street lamp

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

Cathedral of St. Mary the Virgin, Tallinn, Estonia

Also known as the “Dome Church,” this is Estonia’s oldest church, built sometime before 1233.

The inside is decorated with elaborate medieval coats of arms, and tombstones pave the floor.

You can climb to the top of the 226-foot spire for incredible views of Tallinn Old Town below.

5) Raekoja Plats (Tallinn Old Town Square)

Raekoja Plats (Tallinn Old Town Square)

The Town Hall Square bustles with life.

Thankfully, benches invite you to sit down and engage in some interesting people watching!

We saw a young maiden dressed in period costume, tied to a cart and being dragged along the cobblestone square – advertising  for a museum or medieval dungeon attraction?

The Tallinn Old Town square is also home to the oldest pharmacy in all of Europe, still operating today.

We popped in to buy throat lozenges and Sudafed (for the inevitable travel sniffles).

The Burchardt family established the pharmacy in the 1500s and ran it until the mid-1800s.

As a sideline, they also invented marzipan which, in addition to being delicious, was originally used as a cure for many ills, including flu, headache and jealousy.

Olde Hansa almonds in Tallinn

In Olde Hansa, a restaurant/shop lining the square, we couldn’t resist trying their famous spicy, sugared almonds.


By the way, you won’t go hungry in the city – there are many great cafes and restaurants in Tallinn.

6) Saint Olaf’s Church

Saint Olaf's Church, Tallinn

When Saint Olaf’s Church was built in the 12th century (rebuilt in the 14th century), the idea was to erect a church so tall it would attract ships (and commerce) from miles around.

And at one time – between 1549 and 1625 – the church was indeed the tallest building in the world.

Today, at over 400 feet high, it’s still a recognizable landmark – and one of Tallinn’s most photographed sites!

If you’ve seen photos of Tallinn, you’ve seen photos of Saint Olaf’s Church!

7) Shopping in Tallinn Old Town

You’ll pass lots of cute little shops in Tallinn Old Town.

What catches your fancy?

A sweet pastry?

Amber jewelry?

Cloth dolls or matryoshka (nesting) dolls from Russia?

Russian nesting dolls for sale in Tallinn, Estonia

We usually don’t collect too many souvenirs when we travel, but we do end up collecting lots of photos!

We hope you’ve enjoyed these…

Experience more of Europe!

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Greece: Did you know it’s illegal to wear high heels at the Acropolis? Discover 100+ cool and fun facts about Greece!

Berlin: Is it possible to get a taste of Berlin in one day?

Our top travel tips and resources

Hotels: is great for scoring a “wow” hotel – or at least a decent one. (We especially like their flexible cancellation policy!)

Vacation homes, condos and rentals: We prefer and use Vrbo (Vacation Rentals by Owner).

Tours: For the best local food, walking and other guided tours, plus skip-the-line tickets to attractions, check out Viator (a TripAdvisor company) and GetYourGuide.

Car rental: Renting a car is often one of the best ways to explore off the beaten path. Discover Cars searches car rental companies so you get the best rates.

Travel insurance: SafetyWing is designed for frequent travelers, long-term adventurers and digital nomads. It covers medical expenses, lost checked luggage, trip interruption and more. We also have and recommend Medjet for global air medical transportation and travel security.

Travel gear: See our travel shop to find the best luggage, accessories and other travel gear. (We suggest these comfy travel sandals for city walking, the beach and kicking about.)

Need more help planning your trip? Check out our travel tips and resources guide for airline booking tips, ways to save money, how to find great hotels and other crazy useful trip planning info.

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Tallin Old Town, Estonia

Photo credits: 2, 3, 6 to 15, 17 to 19 © Janice and George Mucalov, SandInMySuitcase

About the authors

Luxury travel journalists and SATW, NATJA and TMAC “Best Travel Blog” award winners, Janice and George Mucalov are the publishers of Sand In My Suitcase. Between them, they’ve traveled to all 7 continents. See About.

Find destination guides, global food-and-wine stories, luxury hotel reviews, articles on cultural explorations and soft adventure trips, cruise reviews, insanely useful travel tips and more!


Friday 30th of December 2016

What a great way to introduce Tallinn! I've never been there, even though I live close by - in Poland. I need to make sure I visit my neighbors soon!

Janice and George

Friday 30th of December 2016

Yes, you'll have to visit Tallinn! So close for you... And by the way, we loved visiting Gdansk in your native Poland too :-). Have a look at our Gdansk post with pictures.

Suzanne Jones

Sunday 18th of December 2016

Tallinn is such a pretty medievel town - some lovely photos which have inspired me to make a return visit. Where did you stay?

Janice and George

Friday 23rd of December 2016

We didn't stay in Tallinn - we visited Tallinn for a day while on our Baltic cruise on the "Viking Star." It would be nice to stay longer though...


Sunday 11th of December 2016

Pretty looking town and the ironwork quite spectacular. Tallinn (and Riga) places we'd like to see, we've never been to the Baltics. I like Orthodox churches - we've just arrived in Belgrade (Serbia) and lots of those onion shaped domes.


Janice and George

Saturday 17th of December 2016

Those onion-shaped domes are quite the sight, aren't they? Very striking... We look forward to reading your Belgrade posts :-). Enjoy!

Irene S. Levine

Saturday 10th of December 2016

Your eyes and camera have captured such wonderful architectural details. What a beautiful place!

Janice and George

Saturday 10th of December 2016

Indeed! Tallinn is a very beautiful port-of-call on a Baltic cruise...

Penny Sadler

Friday 9th of December 2016

I love the boot shaped lamp. And the woman behind the cart, weird. :)

Janice and George

Friday 9th of December 2016

Yes, that boot-shaped drain pipe is a cool feature - but it's easy to miss if you're not on the lookout for it...