Wandering Tallinn’s Medieval Fairytale Streets

Tallinn, a medieval Old Town surrounded by 13-century walls and oozing charm at every turn.

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After loving city breaks in the other Baltic countries on low cost return fares (Riga and Vilnius) , I knew I had to make my way to Tallinn.

Luckily enough, checking off my remaining Scandi countries (Finland, The Faroe Islands) is relatively high priority for me, so looking at a long weekend in Helsinki and realising I could ferry over to Tallinn for a day seemed too good to be true.

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In early September, I flew into Helsinki on a Saturday morning and booked a ferry to Tallinn for that evening. Looking back, I would have stayed in Helsinki all three nights, and instead done the first ferry out/last ferry back on Sunday- would have made luggage storage and a few logistics easier. I was worried about not having enough time in Tallinn, and wanted to start Sunday explorations as early as I could, but as it turned out- I was so exhausted from the day prior, I slept in. And, I needn’t have worried, Tallinn’s Old Town is compact and walkable- easy to see in one day.


Albeit I wasn’t there long, Tallinn didn’t need more than a day to capture my heart. A charming Old Town, beautiful red roofs, picture-perfect cobbled streets- it’s like stepping back in time to the medieval age.

Old Town is so well-preserved, it’s been granted UNESCO World Heritage Status.

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If you’re short on time like I was, I’d recommend starting in upper town, and seeing the city from a few lookouts.

Don’t miss: the Alexander Nevsky Cathedral (so stunning, I’m now inspired to plan a visit to Russia), and three viewing platforms: Toompea Hill (there’s a cute cafe here to have morning coffee from); Patkuli Vaateplatvorm; Kohtuotsa.

I spent a little over an hour in upper town before wandering down to the town below.

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Stop in town square and St. Catherine’s Passage (a lane of local stores and restaurants). I didn’t have much of a to-do list per se, instead, I planned on wandering at leisure and turning down streets when I felt like it. Turned out to be a great plan. I saw just about all of Old Town, and discovered a few gems to have coffee and eat along the way.

  • Eat:
    • Must Puudel: Incredible vegetarian food – we had the tomato hummus, local cheese board and vegetarian ramen. Everything was great, and we appreciated the menu’s focus on healthy eats
    • Von Krahli Aed: Very good Eastern European, focus on ingredients and sustainability. We tried a few of the small plates, along with a few Estonian drinks- a pear cider and apple lemonade with rhubarb
    • Vegan Restoran V: Known for their excellent vegan dishes- we didn’t eat here, but did stop to look at the menu
    • Pierre Chocolaterie: Stop in if you fancy a sweet treat
  • Coffee:
    • The Living Room Cafe: Beautiful coffee shop, perfect place to start a morning in Tallinn
    • Epic Coffee: Down an adorable lane, I was intrigued to stop here to try a Pumpkin latte- autumn in a cup 🙂
    • Maiasmokk: Tallinn’s oldest cafe, not much has changed decor wise here in centuries
  • Drink:
    • Parrot Minibar: Great cocktails and a fun food concept- everything is meant to be eaten in 1-2 bites, so plates are small and flavours are intense (in a really good way)
    • Sigmund Freud Bar: Another good cocktail spot in Tallinn, more of a speakeasy feel
    • Sazerac Bar: Come here, order a sazerac, relax after a long day of exploring the city

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I was surprised by how much I loved Tallinn. It’s becoming a very popular destination, but it didn’t feel crowded- and I was there on a Sunday where there was a city marathon.

Most people say you need 2-3 days in Tallinn. If I had an extra day or two, I would have gotten out of the city, exploring the Estonian countryside or perhaps one of the idyllic islands.

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Have you ever been to the Baltic countries? Which one is your favourite? 

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