
The wind whips through my hair as we walk along the pier to our first glimpses of Estonia. There’s not much by way of sign posts to the Old Town but I know Tallinn is going to be special. Luckily it’s only a short walk and we follow our noses to enter into under the stone city gate.

Tallinn, a UNESCO-listed medieval town, preserves its walls almost completely intact. Within them, Tallinn’s vana-linn (Old Town) offers a picture-perfect escape from modern life into the narrow cobbled streets of the 15th century – aside from the tourists, souvenir shops, restaurants and a few other modern comforts.
This Hanseatic town was part of the Hanseatic League from approximately the 13th to the 17th Centuries. The League being a collection of merchant guilds and market towns in Northwestern and Central Europe, operated for commercial and defensive purposes.

We start at the lower end of town at Fat Margaret’s Tower (which also houses the Estonian Maritime Museum). From here we cross under the stone gates of the city. They are flanked by red roofed towers and decorated with stone carved family crests. I pause to contemplate their age and significance. This particular gate, the Great Coastal Gate, was the main seaward gate and barbican between the port and the town’s market square as far back as 1359. Between 1518 and 1529, builders constructed an artillery tower to further fortify the town amid fears of a Danish invasion. The tower measured about 25 meters in diameter and had walls approximately 5 meters thick. After the Great Northern War (1700–1712), people used the tower variously as a warehouse, barracks and prison. We observe the gate from the outside but give the military museum a miss for now.
From Pikk, where the gate stands, we turn into the town and head away from the gate, follow the city wall for a short distance, then turn onto Lai briefly until we reach Oleviste Kogudus (St. Olav’s Church).

St Olav’s Church dates from the 12th Century. The light, whitewashed interiors highlights the woodwork of its high Gothic vaulted ceilings. There is a tower that can be climbed but there is already a long line. Besides, I’m keen to get to Toompea Hill before the rest of the crowds really set in for the day. We continue up Lai, turning left an Nunne and then crossing under Pika jala väravatorn (the Long Leg Gate Tower). The road itself, known as Pikk Jalg (the long leg) was built to connect Toompea Hill to the low town and harbor for riders and horse drawn carts. The steeper, stepped, Lühikese jala värav (short leg gate) was purely for pedestrian traffic.

In 1380, the town’s feudal lord, Wilhelm von Friemarsheim, issued a license to replace the existing wooden gate with a stone tower. Builders constructed the tower and gateway with a portcullis that could close to protect the town, along with openings for attacking enemies. When the tower no longer served a defensive purpose, people repurposed it for various uses, including housing soldiers. Later still, artists and students lived there.

The Short Leg Gate is a steeply ascending set of stairs intended as a short cut between the lower town and Toompea Hill. The stone gate tower, along with that of the Long Leg, was built around 1455. Fortifications built agains the Toompea area (upper town) meant that the lower town could be successfully defended, even after Toompea had fallen into the hands of the enemy.

We’ve now reached Toompea proper. I can see the domed top of the pink and white Aleksander Nevski Cathedral, a Russian Orthodox cathedral built in the last decade of the 19th Century whilst part of the Russian Empire. Inside it is large and fairly typical of the style and time with a beautifully decorated iconostasis.

Back out into the bright sunshine. We pass Tall Hermann’s Tower and Toompea Castle which today houses the Parliament of Estonia. It doesn’t appear that we can visit so we continue on to another church nearby, the Cathedral of St. Mary the Virgin, known as the Dome Church. The area is starting to get busy and a couple of tours appear to have arrived so I (somewhat reluctantly) give this one a miss, pressing on until the sweeping view from a scenic lookout is upon us.
From here at the top of Toompea Hill, the red roofed city huddles below us. We can’t see all of it from here but the section of the wall with its towers that sit like jewels set onto a necklace, albeit a slightly broken one, prettily accent the curve of the ramparts that protect the rest of the town.

After a suitable pause to appreciate the breathtaking view, made even more so by the bright blue sky and sun shining on the red topped towers, despite the wind that blows.
We double back before we get swept away by the wind (as opposed to the views) with a pause in the Bishop’s Garden for a little rest stop and views over the park below. St Mary’s is still too busy so we give the Dome Church a miss and round Aleksander Nevsky Cathedral again on the way to Kiek in de Kök a restored 15th Century canon tower. Now a fortifications museum consisting of a fascinating four towers and the wall walk ramparts that join them.

We enter via Neitsitorn (the Maiden’s Tower) which was erected in 1370. This square defense tower now houses the museum cafe and has great city views but beware of ghosts! The largest tower is Kiek in de Kök, built in 1483. This is the largest medieval artillery tower in the Baltic states with false ceilings and secret tunnels making it so much larger than it first appears. The many false ceilings make it seem like you’re at the top until another secret passageway is climbed and you find yourself on another level altogether.
The stable tower (1380) houses a watchtower and dungeon and finally connects to the Gate Tower of the Short Leg (1454) which is the historical connection between Toompea and the lower town.

The Danish King’s Garden connects them all at ground level and serves as the city’s courtyard, where workers cast cannons and church bells. Bastion passages (1710) also link them through outer routes along the walls and through secret inner passages.

Inside there are various displays. From historic battles and the establishment of the medieval town, including its defenses. Through to the cafe culture of Tallinn in the early 20th Century and it’s excellent confectionery industry.

We can’t resist an afternoon coffee, paused at the cafe on the ramparts overlooking the town. After our refreshments and another pause to contemplate the black monks of the Danish King’s garden, we take the path down past the Short Leg Gate towards the town hall square.

The square is absolutely buzzing. There are people everywhere – sitting outside enjoying lunch with beer, taking coffee and cake and many, many more making photos. I love the European expressions (interpretations) that one ‘makes’ a photo (rather than takes) and ‘takes’ a coffee (rather than has).
We make our own photos in the square and then split up. Jason is keen to pause to take in the atmosphere and a beer and mum and I are keen to explore the walls and towers a little more and there is a monastery that I would like to find.

More time is spent exploring the pretty cobbled streets and surprising nooks whilst I am ultimately on a mission to find the Dominican monastery of St. Catherine’s. We check out the St Catherine’s passage whilst on the hunt, with tombstones hung on walls and the charm of the surrounding cafes, shops, arts and crafts.

Failing to find the monastery we stumble across the entrance to the Hellemann Tower and town wall walkway. Not wanting to regret the opportunity of another great find, we pay our few Euros and climb to the top. Here we take in more wooden walkways and views of roof times and alleyways.
After our descent I want one more chance to find the monastery and finally, after another series of false turns, we stumble upon the entrance. ‘Aite’, the friendly ticket seller writes it down for us and I finally learn how to say ‘thank you’ in Estonian. If I don’t see it written down, I’ll never remember.

The Dominican monastery, founded in 1246, aimed to spread Christianity and strengthen the Catholic Church’s influence. Like all good monasteries, the buildings inter connect with ambulations to form an open quadrangle. Unlike typical designs, the church forms one side, and enclosed cloisters replace open porticoes (see Santa Chiara)..
After the Reformation around 1525, the monastery closed and later served various civic purposes. People used it as a school, hospital, arsenal and private residence over time.
Today, the church remains active, and the monastery operates as a living museum.
Visitors can explore archaeological finds displayed within the courtyard.

It’s only a small area but we spend some time reading about the history and enjoying the peacefulness. The hushed courtyard space with grass and wild summer flowers in bloom is particularly enjoyable.
Tallinn’s Old Town showcases a rich collection of historic buildings and architectural heritage. Visitors can explore well-preserved city walls and towers throughout the area.
Notable sites include dwellings from 1346, Lai 23 (1551), and Toom-Kooli 1 (1776).
Other highlights include Stenbock House and the medieval merchant’s house at Vene 12.
The terrace building at Olevimägi 11 (1825) adds further architectural interest. Visitors can also see the former home of architect Rudolf von Bernhard at Pikk 62.

Snaking our way back through the narrow cobbled streets we pass back under the gate to the port. The wind gusts as we make our way towards the dark Baltic Sea. I glance back and can still see the red topped towers through my wind whipped hair. I don’t want to go, Tallinn would make a wonderful, romantic weekend escape. As so many of these small old towns, there is more here than meets the eye.
Would I Return?
Yes. Tallinn is an enchanting town to explore. Much less affected by WWII than many other places along the Baltic Sea, it retains its medieval charm. Yet it is still well versed in welcoming tourists to its shores. Thankfully, this does nothing to alter the utter charm of Tallinn.

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