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Tallinn, Estonia seems to be a new darling in the travel world, and I felt compelled to add it to our itinerary when visiting St Petersburg, Russia this month. Like another popular walled city, Dubrovnik, the Old Town of Tallinn has something of a Disney-esque, fairy-tale quality at first glance. In spite of a few kitschy, historically-garbed locals and an overabundance of souvenir shops with near-identical merchandise, Tallinn lives up to its accolades.



There are hundreds of perfect little shops, charming cobblestone streets, and dozens of appealing restaurant and lodging options, all concentrated in a small, very walkable area. And luckily, there is also some interesting history behind this picture-perfect façade. On the shores of the Baltic Sea, the Old Town started as a medieval trading city (then called Reval) in the 13th century and developed as a center of the Hanseatic League, a group of European trading cities.


Today, the stone walls and buildings are remarkably well preserved, and Tallinn’s Old Town is deservedly a UNESCO World Heritage Site. An upper town, called Toompea, sits above the Old Town on a limestone hill; now as in the past, this part of the city houses the administrative center of the city and country. The capital city’s current Parliament building is part of the original town castle here, and the impressive Alexander Nevsky Cathedral, among other structures, graces the hill overlooking the Old Town.

We were glad we jumped on a bus to see some other parts of Estonia’s capital. We passed first through City Center, which was not particularly noteworthy but offered a view of more modern-day Tallinn. A sizable chunk of the city’s inhabitants lives east of the city in a bedroom community called Lasnamäe; here there are very large, bland apartment blocks, many built in the ‘70s to the ‘90s, all anchored in a grim, multi-layered limestone shelf.

Circling back to town, we passed through Kadriorg, a beautiful old neighborhood of colorful wood villas dating back to the 19th century. Kadriorg Palace is yet another palace built for Catherine I of Russia by her husband Peter the Great; this one served as a summer retreat for the royal family and with its natural parkland and many museums, the Kadriorg area remains one of the wealthiest and most picturesque parts of Tallinn today. The Kalamaja neighborhood likewise features quaint painted wood buildings, but here in this gentrifying former fisherman’s area, the overall feel is shabby-chic, fun, and artsy. Home to many students, this part of town contains a number of hipster cafes and bars and is also an easy getaway from the throngs in Old Town.

Tallinn offers a tantalizing array of narrow, twisting streets, medieval towers and walls from which to view the city’s colorful rooftops, details like heavy wood doors and iron adornments, a vibrant Christmas market in the main town square, lively coffee shops and bars, a sparkling ice skating rink near the center of town, and dining options from upscale to simple local eateries.


Two days is plenty to take in all the city has to offer, but it definitely merits more than the day-tour stopover many people make it from Helsinki. If your travels take you to either St Petersburg or Helsinki, consider hopping a train or bus (6-7 hours from St Petersburg) or a ferry (2 hours from Helsinki) to this appealing old-world city.