Tallinn’s UNESCO-protected old town has winding alleyways and medieval courtyards.

Our Day in Tallinn was like living a day back in Medieval Times.

This pair of picturesque, ivy-covered towers at the entrance to Viru Street is often the first glimpse visitors get of Old Town. Anyone passing between them couldn’t be blamed for thinking they’ve left the 21st century behind and landed smack in the middle of the 18th. The towers are actually only the foregates of what was a much more complex gate system built in the 14th century. It included a large, square tower that stood father back along the street, close to where the city wall can be seen. Most of the gate was pulled down in the 1880s to make room for traffic, but these two towers remained and have since become a symbol of the town.

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: In one terrible night, on March 9, 1944, Tallinn was hit, and the area around this church—once a charming district, dense with medieval buildings—was flattened.

From the church, we climbed the steep, cobbled, Lühike jalg (“Short Leg Lane”). It was a narrow street lined with quality Estonian craft shops.

The Danish King’s Garden is centrally situated on Toompea Hill between the city wall and lower Tallinn. Basically it is just a small garden-like square with a medieval feel to it, but there’s an interesting story behind the garden, which makes it a special place for Danes and Estonians. According to the legend, in the 12th century the Danish King’s (Valdemar II) forces were losing a battle with the Estonians when all of a sudden a red flag with a white cross floated from the open sky. This was interpreted as a heavenly and victorious sign from God, and the course of the battle turned in the Danes’ favour making them rulers of Tallinn and Northern-Estonia for over a hundred years.

Upper Town – Toompea

The whole troop marching down Puhavaimu.

By the Chocolaterie.

Katariina Käik, a lane with local artisan shops.

Due to its peculiar menu and interiors, Balthasar has become a popular restaurant among locals. Starting from appetizers and ending with desserts, you can pick between various levels of intensity of garlic flavour.

Lower Town – Hanseatic Trading Center

Tallinn, Estonia’s capital on the Baltic Sea, is the country’s cultural hub. It retains its walled, cobblestoned Old Town, home to cafes and shops, as well as Kiek in de Kök, a 15th-century defensive tower. The city once consisted of two feuding medieval towns separated by a wall. The upper town—called Toompea—was the seat of government ruling Estonia. While the lower town was an autonomous Hanseatic trading center filled with German, Danish, and Swedish merchants who hired Estonians to do their menial labor.

Town Hall Square is reminiscent of pages from a children’s fairytale book.

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.

Toompea castle was an ancient stronghold site in use since at least the 9th century. Today, it houses the Parliament of Estonia.

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. While it’s still a functioning pharmacy, the decor goes back to medieval times and welcomes guests with painted ceiling beams, English descriptions, and long-expired aspirin.

Its Gothic Town Hall, built in the 13th century and with a 64m-high tower, sits in lower town’s main square. Beyond the hill is the commanding Russian Orthodox Cathedral, as well as the pink palace known as Toompea Castle. 

We were curious to see the views from the top of the city walls. We climbed a tall spiral staircase and stepped into this narrow plank balcony.

Strolled atop this 200m stretch of Town Wall for fantastic views of Tallinn’s medieval defences. This three-storey tower, which stands adjacent Müürivahe street next to Old Town’s knit market, dates back to the 14th century and at different times was used as a prison and a weapons store.

The “Sweater Wall ” – a colourful and tempting gauntlet of women selling handmade knitwear.

Capuccino views along Viru Street – old Tallinn’s busiest and kitschiest shopping street.

Those decadent desserts in Cafe Maiasmokk – oldest cafe in Estonia.

These flower stalls were inviting contrasts to the grey medieval walls of Tallinn’s Old Town.

Spring bouquets in full bloom!

It was such a small navigable complex that we left our senses free to take us anywhere. The day was at leisure, as we got lost and pleasantly discovered interesting things.