Day 1: Kalamaja & Telliskivi Creative City
Flights from the US usually take upward of 14 hours and include a connection in larger cities like Oslo, Helsinki, or Moscow. Fares can run past $1,000, but you may be able to save by hitting one of these cities first, then traveling to Tallinn later with one of Europe’s low-cost airlines (or in the case of Helsinki, taking the ferry). In general, buses and ferries are much cheaper, but they rack up a lot of travel time (though there are some good overnight options).
Tallinn’s got a fair spread of lodgings including hotels and Airbnbs. Kalamaja is the cool, trendy neighborhood to stay in, with the best bars and restaurants nearby. Old Town is also convenient, but be forewarned of cruise ship crowds and late-night street noise on the weekends.
Once you’re refreshed and ready to roam, start with a smorgasbord brunch at Balti Jaama Turg (Baltic Station Market). The market hall was restored in 2017 out of old limestone warehouses. Even early in the morning, there are hundreds of vendors and a good crowd grabbing a meal before escaping to Latvia, Lithuania, and onward at the main railway station.
We especially dig the Taiwanese steamed buns and Georgian khajapuri (like a calzone, only cheesier, and therefore better). Also, don’t miss the fresh produce stands on the main floor with baskets of plump berries, when in season, and lightly pickled cucumbers.
From there, it’s a short walk to Kalamaja -- once a defunct fishing district, now the epicenter of Tallinn’s creative upsurge. At Telliskivi Creative City, factory warehouses have been revamped into showrooms for Estonian designers (check out Stella Soomlais, a local leather designer whose stylish belts and purses carry a lifetime repair warranty), vintage boutiques, antique dealers, and third-wave cafés. There’s also a weekly flea market of funky Soviet antiques on Saturdays.
Try the organic ice cream at La Muu, or a bite atop the Fotografiska Tallinn’s rooftop zero-waste restaurant. Some of the best views of the industrial landscape, plus graffiti murals and poppin’ crowds, can be seen from up here. Afterward, take the elevator down to Fotografiska’s exhibitions. This is not a museum to rush through. Fotografiska pulls top photographers; last year they included Jimmy Nelson and his portraits of remote indigenous tribes, and Alison Jackson’s satire of tabloid culture (including mock shots of Trump that you’ll never be able to unsee).