A Visual Walking Tour of Tallinn, Estonia

If you need some travel advice, Rick Steves is your guy. He's traveled everywhere. I first discovered him through his podcasts about Spain, and I knew to seek them once again when we were gearing up for Scandinavia and the Baltics.


The only time I had heard of Tallinn was when one of my favorite bloggers, Chelsea Lankford, went on a Baltic Sea cruise with Princess. Her photos were the only impressions I had of Tallinn before going, and I have to say, Tallinn is just as charming, if not more, as she and Rick say it is.

Old Town is a UNESCO World Heritage Site; walking into this part of the city really feels like you're walking into a medieval storybook. I'll warn you that tons of cruise ships are docked during the cruising/tourist season, so if you do go during that time, expect large crowds!

Russian Cathedral

When I was researching "things to do in Tallinn", I found myself overwhelmed by the abundance of options. The biggest downside to cruising is that you don't get enough time in one port - 6 hours isn't sufficient to get to know a city. A tour guide is great because they know the city through and through; they'll show you what's worth seeing within your time frame. At the same time, we wanted a balance between self-exploration and guided tours, and we'd already planned tours for other cities.

Exploration is great (what better way to learn about a place than to get lost?), but when you're tight on time, getting lost over and over again is just stressful (you're asking for a silent family dinner later that night). We found that Rick Steves's "Self-Guided Walking Tour of Tallinn" guide was a great balance between the two - we were able to see the most notable sights and learn a little about each's history according to our own pace.

This guide is detailed enough that you'll be able to navigate the twisty, cobblestone streets fairly easily. I do recommend printing out a city map to supplement the directions Steves provides.

What this guide lacks, however, are images - it's nice to have an idea of what you should be looking for, right? This post is a pairing of my photos with quotes from Steves' guide - his quotes are italicized, and my comments are in normal font.

I hope you fall in love with this medieval city!

(Find Rick Steves' full walking tour guide here: https://www.smithsonianmag.com/travel/a-walking-tour-of-tallinn-5779/)

As you walk towards Old Town from the ferry terminal,
you have the option to walk through a tunnel - the lighting there is great!

[1] To Fat Margaret Tower and Start of Walk: From the ferry terminal, hike toward the tall tapering spire, go through a small park, and enter the Old Town through the archway by the squat Fat Margaret Tower. Just outside the tower on a bluff overlooking the harbor is a broken black arch, a memorial to 852 people who perished in 1994 when the Estonia passenger ferry sank during its Tallinn-Stockholm run. The details remain murky, and conspiracy theorists still think Sweden sank it. (The boat went down very quickly; Sweden has never allowed any divers to explore the remains, and now there’s talk of entombing it in concrete, leading some to believe the incident involved some kind of nuclear material-related mischief.)

Fat Margaret Tower guarded the entry gate of the town (in medieval times, the sea came much closer to this point than it does today). The relief above the gate dates from the 16th century, during the Hanseatic times, when Sweden took Estonia from Germany.

Broken arch

Fat Margaret

Three Sisters

Just inside the gate, you’ll feel the economic power of those early German trading days. The merchant’s home nicknamed the “Three Sisters” ... is a textbook example of a merchant home/warehouse/office from the 15th-¬century Hanseatic Golden Age. The charmingly carved door near the corner evokes the wealth of Tallinn’s merchant class.

Pikk Street (St. Olav's Church is featured in a later photo...and my mom is so cute!)

[2] Pikk Street: This street, the medieval merchants’ main drag leading from the harbor up into town, is lined with interesting buildings—many were warehouses complete with cranes on the gables. You’ll pass St. Olav’s Church (Oleviste Kirik, a Baptist church today), notable for what was once the tallest spire in Scandinavia. 

While tourists see only a peaceful scene today, locals strolling this street are reminded of dark times under Moscow’s rule. The KGB used the tower at St. Olav’s Church to block Finnish TV signals. And the ministry of police (nearby at Pikk 59) was, before 1991, the sinister local headquarters of the KGB. “Creative interrogation methods” were used here. Locals well knew that “from here started the road of suffering,” as Tallinn’s troublemakers were sent to Siberian gulags. 

From #36, what's supposed to be the "Navitrolla Galleri". (We didn't see any "whimsical, animal-themed prints".)

The Navitrolla Gallerii (at #36) is much happier, filled with art by a well-known Estonian artist. His whimsical, animal-themed prints are vaguely reminiscent of Where the Wild Things Are.

Hall of the Black Heads Society (1st yellow building)

Farther up Pikk, the fine Hall of the Black Heads Society (at #26) dates from 1440. For 500 years, until Hitler invited Estonian Germans “back to their historical fatherland” in the 1930s, this was a German merchants’ club.

Today the hall is a concert venue. Its namesake “black head” is the head of St. Mauritius, an early Christian martyr beheaded in Switzerland (A.D. 200). Reliefs decorating the building recall Tallinn’s Hanseatic glory days.

Art Nouveau 

Church of the Holy Ghost

[3] Great Guild Hall: Pikk, home to the big-shot merchants, feels Germanic because it once was. The Great Guild Hall was the epitome of wealth, with its wide (and therefore highly taxed) front.

Across the street, at #16, the famous Maiasmokk (“Sweet Tooth”) coffee shop, which was the sweetest place in town during Soviet days, remains a fine spot for a cheap coffee-and-pastry break.

[4] Church of the Holy Ghost (Pühavaimu kirik): Sporting a great clock from 1633, the church is worth a visit. The plaque on the wall is in Estonian and Russian. Before 1991, things were designed for “inner tourism” (within the USSR). 

Town Hall Square

[5] Town Hall Square (Raekoja plats): A marketplace through the centuries, this is the natural springboard for Old Town explorations. The cancan of fine old buildings is a reminder that this was the center of the autonomous lower town, a merchant city of Hanseatic traders.

The 15th-century Town Hall (Raekoda) dominates the square; it’s now a museum, and climbing its tower earns a commanding view. On the opposite side of the square, across from #12 in the corner, the pharmacy (Raeapteek) dates from 1422 and claims—as do many—to be Europe’s oldest.

[6] Wheel Well (not photographed): The well is named for the “high-tech” wheel, a marvel that made fetching water easier. Most of the Old Town’s buildings are truly old, dating from the 15th- and 16th-century boom-time. Decrepit before the 1991 fall of the USSR, Tallinn is now more affluent and has been quickly revitalized. 

St. Nicholas' Church

[7] St. Nicholas’ (Niguliste) Church: This 13th-century Gothic church-turned-art-museum served the German merchants and knights that lived in this neighborhood 500 years ago. The Russians bombed it in World War II

The exterior of the Danish King's Garden

[8] Danish King’s Garden: Stand in the former garden of the Danish king. The imposing city wall once had 46 towers—the stout, round tower way ahead is nicknamed “Kiek in de Kök.” 

A great view of St. Nicholas' Church from the garden

Russian Cathedral

[9] Russian Cathedral and Toompea Castle: The Alexander Nevsky Cathedral was built here in 1900 over the supposed grave of a legendary Estonian hero—Kalevipoeg. While it’s a beautiful building, most Estonians don’t like this church. Built to face the national parliament, it was a crass attempt to flex Russian cultural muscles during a period of Estonian national revival. Step inside for a whiff of Russian Orthodoxy; about a third of Tallinn’s population is ethnic Russian

[10] Tall Hermann Tower: The tallest tower of Toompea castle's wall

Tall Hermann

St. Mary's Cathedral ("Dome Church")

[11] Dome Church (Toomkirik): Estonia is ostensibly Lutheran, but few Tallinners go to church. A recent Gallup Poll showed Estonia to be the least religious country in the EU—only 14 percent of the respondents stated that religion is an important part of their daily lives. Most churches double as concert venues or museums. 

She was playing right outside of St. Mary's Cathedral (Dome Church) - she hit every note perfectly! 

Patkuli Viewpoint: St. Olav's Church rises above all of Old Town. To its left, in the distance, is the red TV tower.

[12] Patkuli Viewpoint: Beyond the lower town’s medieval wall and towers stands the green spire of St. Olav’s Church, once 98 feet taller and, locals claim, the world’s tallest tower in 1492. Beyond that is the 985-foot-tall TV tower (much appreciated by Estonians for the heroics involved in keeping the people’s airwaves open during the harrowing days when they won independence from the USSR). During Soviet domination, Finnish TV was responsible for giving Estonians their only look at Western lifestyles. Imagine: In the 1980s, many locals had never seen a banana or pineapple—except on TV. 

View from Kohtuotsa Viewpoint

[13] Kohtuotsa Viewpoint

There have been several photos of musicians in this blogpost - music, especially folksongs, is deeply rooted in Estonian culture and history.

Ending our tour of Tallinn back near Town Hall Square - it's full of cafes and restaurants.

Kaarli Boulevard

P.S. If you find yourself with a bit of spare time in Tallinn, I recommend Apollo bookstore in Solaris Shopping Centre! My brother led us into the store, and we ended up spending quite a bit of time there. Stationary, literary, and souvenir junkies alike will enjoy it. 

(Find Rick Steves' full walking tour guide here: https://www.smithsonianmag.com/travel/a-walking-tour-of-tallinn-5779/)