I’ve Visited Over 40 Countries & This Medieval Town Is Europe’s Best Destination

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Guys, I found Europe — real Europe.

You know the visual:

Storybook streets brimming with Old World delights, timeless marvels catching your eye in every corner of the town center, and inviting open plazas with indescribably meticulous detail you just have to see to believe.

The town I visited is steadily growing in the travel scene, but not yet a household name by any measure.

If that were the case, people would have flocked here during the heyday of Shrek-mania, hoping Lord Farquaad himself might walk out of the towering 13th-century castles anchoring Old Town’s dreamscape.

Still clinging to “hidden gem” status, I believe Estonia's storied capital is Europe's best destination right now for a myriad of reasons.

Take it from me, someone who has visited 43 countries — many of which are European — from up-and-coming Moldova, bustling metropolises like Paris, and Portugal's golden secret.

From my latest loop around Europe, as I write this piece on my flight home (assuming Lufthansa's spotty wifi held up….), there's no doubt the medieval town of Tallinn will be tattooed in my mind's eye as the version of Europe most travelers imagine, but few actually experience.

Hear Ye, Hear Ye! Time Travel In Tallinn

Let's start backwards — I did not want to leave Tallinn. Not at all.

In fact, I wish I had based our trip around this medieval charmer instead of larger cities, but hey, even seasoned travelers make mistakes…

It's been a minute since I've had the pleasure of visiting a textbook fairytale town — one that truly wowed me.

The closest comp I have would be Luxembourg (or maybe Bratislava) but there are probably better examples that I've yet to visit.

Tallinn captivated both myself and my girlfriend Sara from the moment we caught a glimpse of the cobblestoned town center.

For the record, I say “town” loosely. Tallinn is the capital city of nearly half a million residents, but once you’re in the heart of Old Town, it feels small, even with its labyrinth of stone walkways; you could immerse yourself in another time for hours on end — or at least, we certainly did and loved every second.

Tallinn is so historic, exuding an old-world atmosphere that’s almost impossible to match, we half-expected a scroll to be rolled out every time we ordered food — perhaps prefaced with a dramatic “Hear ye, hear ye!”.

Obviously, we ordered just fine in plain English (yes, Estonians are largely fluent), but I’m not sure I’ve ever visited a city with such a tangible sense of bygone eras as Tallinn, making it a truly one-of-a-kind must-visit.

Travel Tip: Avoid eating at Olde Hansa — it may seem appealing but it's practically Tallinn's version of Medieval Times (not authentic, overpriced, and gimmicky).

Why My Neck Hurt From Tallinn's Magical Christmas Market

Look, I get it — an American's perspective on Europe's Christmas markets may be about as insightful as ordering a well-done steak with a side of ketchup.

But like I said, I've been to many, many places across Europe during the magic of winter, and Tallinn is by far my favorite Christmas market destination for its centuries-old setting, affordability, lack of crowds, and sensational goodies served from an array of vendors.

The atmosphere here was one for the books in Tallinn's UNESCO-protected Old Town, especially the main square where the town's largest Christmas market is held (and still ongoing through December 28 for a few extra days of holiday cheer!).

Believe it or not, the bed at my Airbnb straight out of Hänsel und Gretel was more comfortable than Helsinki's new Waldorf Astoria, so I know my neck was hurting because I could not stop looking up at the Town Hall's magnificent weathered-stone medieval facade, capped with skyward spires, towering over us as we sipped Glühwein, ate way too many sausages, and overstuffed ourselves with sugary treats.

There's nowhere else in Europe I've felt more, and hope to be able to visit again before it's held in the same regard as Prague, Munich and the likes.

Tallinn is Set To Surge!

Over the next year or so is the perfect time to add Tallinn to your wishlist as it's currently not crowded, but may be in the near future.

As Tallinn has welcomed more visitors, including a hefty amount of digital nomads during sunnier months, this dreamy getaway has become enticing for all types of travelers — and I'm here to tell you I've seen how cities can change at the drop of a hat, trying too hard to cater to tourists.

So let's hope my favorite Tallinn pub Hell Hunt keeps its local soul and Starbucks' inevitable takeover stays at a minimum.

Despite being relatively low-key at the moment, there are many connections across Europe to reach Tallinn, so it's feasible to get here with just a single layover from the U.S.

Plus, Tallinn's airport is currently undergoing an expansion to accommodate an all but certain influx of tourists.

My recommendation would be to fly to Helsinki if you can, then hop aboard a Viking Line ferry across the Baltic Sea, where it's more like a mini-cruise with slot machines, pubs, and surprisingly delicious food to fuel up on the 2 and half hour journey.

I paid just $17 for my ticket and it was beyond worth it.