Tallinn, Estonia: The Medieval Fairytale You’ll Want to Move To

I’ve been to 112 countries, and somehow, this tiny capital on the Baltic Sea keeps pulling me back.

Tallinn isn’t loud about its beauty — it’s not Paris or Rome or even Prague. It’s quieter, quirkier, and moodier. It feels like a fairytale city that never got the memo about becoming a tourist cliché.

And right now, I’m spending two full weeks here — again — because honestly, Tallinn just won’t let me go.

Getting to Tallinn

Tallinn might look out of the way on the map, but it’s surprisingly easy to reach — especially if you use points and miles.

Finnair is your best option. You can fly from the U.S. to Helsinki, then connect onward to Tallinn on a 15-minute flight, which is basically a scenic blink across the Gulf of Finland.

Here’s what that’ll cost you:

• 27,500 Atmos Rewards points

• 22,500 American Airlines miles

• 30,000 Finnair Avios (and less when there’s a transfer bonus)

If you’re team Aeroplan, both Swiss (via Zurich) and Lufthansa (via Frankfurt or Munich) also get you here in style.

From the East Coast, it’ll run you 40,000 Aeroplan points in economy or 70,000 in business:

Other options include Turkish Airlines, LOT Polish, and Scandinavian Airlines, but availability and pricing are less ideal.

And since Estonia is part of the Schengen Zone, you can easily combine it with trips to Helsinki, Stockholm, or Copenhagen, without dealing with extra visas or paperwork.

Where to Stay in Tallinn

Tallinn’s hotel scene is way better than most cities its size — boutique gems, brand-name comfort, and a few hidden luxury steals.

Hyatt Place Tallinn is a quiet Category 2 property that starts at 6,500 points per night (or about $90 cash).

The points value is fine, but honestly, this is one of those cases where paying cash wins. We’re talking modern rooms, walkable location, and 500 bonus points per night through the end of this year.

If you’re loyal to Marriott, the Hotel Telegraaf is a dream.

It’s housed in a 19th-century telegraph building in the heart of Old Town and oozes character. Cash rates hover around $231, or 37,000 points — a perfect spot to burn those annual free night certificates from Marriott’s cobranded credit cards.

And then there’s the Hilton Tallinn Park, the city’s sleekest “proper hotel.”

Think skyline views, full-service spa, and a short walk or bike ride from the Old Town walls — all for barely $100 a night or around 40,000 Hilton points.

There are a few other options, but those are my personal recommendations.

What to See, Eat, and Experience in Tallinn

Dive into history — literally

About an hour outside the city, the Rummu Quarry offers one of Europe’s most surreal scuba diving spots.

Once a Soviet-era prison and limestone mine, it’s now flooded and crystal-clear — filled with submerged buildings, machinery, and forests frozen in time.

You can take a bus from downtown Tallinn or book a guided tour. I did this three years ago, and it remains one of the most unique things I’ve ever done.

Sip the best beer in Estonia

Head to Põhjala Brewery, just outside the city center.

Try their Kosmos IPA, grab some food, and if you’re like me, leave with a T-shirt that earns permanent residency in your travel backpack.

The brewery also has a sauna… because… of course it does. 😂

Eat like it’s 1473

Olde Hansa, a medieval-style restaurant in the Old Town, serves only ingredients that existed in the 15th century — no potatoes, no tomatoes, no coffee.

Expect candlelight, costumed servers, wild game, honey beer, and lute music that makes you feel like you’re eating dinner in The Witcher. It’s touristy, yes, but completely worth it.

Wander through ancient architecture

Climb the Kiek in de Kök Museum (and try not to laugh when you say the name out loud) and Bastion Passages, explore medieval towers, and walk the city walls for unreal views of red rooftops and the Baltic Sea.

Eat pancakes the size of your face

Kompressor Pub is a local institution — they serve giant, fluffy pancakes stuffed with everything from ham and cheese to berries and whipped cream. 🤤

Bring friends (or an appetite… or both).

Explore the creative side

At Telliskivi Creative City and Balti Jaam Market, old factory buildings have been turned into cafés, record shops, design boutiques, and food halls.

You’ll find craft beer, vintage markets, art galleries, and some of the best people-watching in Northern Europe.

Spa like a local

Estonia takes spa culture very seriously — it’s a lifestyle here.

The best one in Tallinn (in my humble opinion) is Elamus Spa, a modern wellness complex where you can spend hours moving between saunas, plunge pools, and aromatherapy rooms.

Estonians see it as therapy, not indulgence — and once you go, you’ll understand why.

Bonus Adventures

• Take the ferry to Helsinki. It’s only two hours across the Baltic, and tickets are cheap (often under $30 one-way). You can literally have breakfast in Tallinn and lunch in Finland.

• Visit Kadriorg Park and Palace, the baroque masterpiece built by Peter the Great. The museum inside is lovely, but the gardens are the real showstopper.

• Climb Toompea Hill for the best panoramic views in the city. It’s especially magical at sunset when the church spires glow a golden color.

• Visit Fotografiska Tallinn, the satellite of Stockholm’s world-famous photography museum, housed in a beautifully repurposed industrial space in Telliskivi (with a rooftop bar and restaurant).

Why I Keep Coming Back to Tallinn

Tallinn is that rare mix of ancient and alive. It has the storybook charm of a medieval capital, the edge of a post-Soviet reinvention, and the calm confidence of a place that doesn’t need to try too hard.

It’s also one of the most walkable, cozy, affordable, and creative cities in Europe — and every time I leave, I already start planning my return.

So if you’re looking for a destination that’s old but new, quiet but buzzing, and touristy yet authentic, you might just find yourself like me… stuck in Tallinn’s spell. 🪄