The oldest capital city in northern Europe, Tallinn—or Reval as it was known for most of the last 600 years— first appeared on a map in 1154 and its Old Town is a UNESCO World Heritage Site. For a city whose history reaches back beyond the Teutonic Knights, Tallinn as also been described by The New York Times as “as sort Silicon Valley of the Baltic Sea” and the success of the IT sector here is reflected in the city’s modern business area. Tallinn was also named the European City of Culture in 2011, cementing its growing reputation as a cultural hotspot. Tallinn's tiny Old Town, the most impressive in the region, has romantic towers, ankle-wrenching cobblestone streets, cozy nooks, city-wall cafés, and a dozen other attractions—all within 1 square km (½ square mile). In the 1990s, Vanalinn (the lower Old Town)—historically the domain of traders, artisans, and ordinary citizens—sprouted glitzy neon signs in otherwise charming alleys and sights. The stately, sedate Toompea (Upper Town), a hillock that was the site of the original Estonian settlement, is on the burial mound of Kalev, the epic hero of Estonia. Toompea Castle, crowning the hill, is now the seat of the country's parliament and is not open to visitors. Summer visitors can experience the unforgettable white nights, when the sun never completely sets.
Tallinn has a wide range of crafts on sale. Fragrant juniper wood is carved into bowls and dolomite stone is fashioned into candlesticks and coasters. A whole range of handblown glass, ceramics, delicate wrought iron, and art is sold in tiny galleries. Hand-knitted sweaters, gloves, and socks keep the locals snug in winter and are signature souvenirs here. Warming quilts are also available, as well as a good range of leather goods. Sweet tooths will love the chocolates made by Kalev and the hand-painted marzipan that's sold in presentation boxes. The Old Town is the place to browse, with some excellent shops around Katerina kälk (Catherine Passage).
The art nouveau interior compliments the French-influenced menu of highbrow European food like beef Stroganoff or tournedos Rossini. To maintain its tradition of decadence, Gloria offers a tabacalera (tobacco shop) complete with Cuban cigars and an extensive wine cellar.
In a 15th-century building in the Old Town, this restaurant recreates medieval times with waiters in period costume, candlelit tables, and historic Eastern European recipes for such dishes as nobleman's smoked filet mignon in mushroom sauce and wild boar with game sauce and forest berries. The honey beer is out of this world, and the old-fashioned food is always fresh and tasty.
Dominiiklaste Kloostri Muuseum
Wander through the ages in the ancient stone galleries and narrow hallways of the Dominican Monastery Museum, founded in 1246 and now displaying 15th- and 16th-century stone carvings. At 5 pm enjoy a half-hour baroque music concert.
At the southern end of the Old Town looms this magnificent, six-story tower church (the name is Low German for "peep in the kitchen"), so called because during the 15th century one could peer into the kitchens of lower town houses from here. The tower has a museum of contemporary art and ancient maps and weapons.
The stocky guardian of the northernmost point of the Old Town, Fat Margaret, is a 16th-century fortification named for a particularly hefty cannon it contained. Now it houses the Maritime Museum and a roof with a view of Old Town.
Kadriorg Palace Foreign Art Museum
The baroque palace, built for Catherine I by her husband Peter the Great in 1721, merits a visit not just for its impressive and thorough exhibition of 16th- to 20th-century art, but also for the palace's architectural beauty and manicured gardens. Kadriorg Palace offers a glimpse into history, from Russian imperial splendor to Soviet Socialist Realist art, with Estonian and European masterpieces along the way.
Aleksandr Nevski Khram
The 19th-century Russian Orthodox Alexander Nevsky Cathedral, with the country's largest bell, is a symbol of the centuries of Russification endured by Estonia.
Rocca al Mare
A 15-minute taxi ride from the center, the 207-acre Open-Air Ethnographic Museum provides a breath of fresh air and an informative look into Estonia's past, from farm architecture to World War II–era deportations.
The 15th-century Church of St. Nicholas, part of the Estonian Art Museum, is famed for its fragment of a treasured frieze, Bernt Notke's (1440–1509) Danse Macabre, a haunting depiction of death.
Tallinn's Town Hall Square has a long history of intrigue, executions, and salt (Tallinn's main export in the Middle Ages). You can tour the only surviving Gothic town hall in northern Europe. Old Thomas, its weather vane, has been atop the town hall since 1530. Near the center of the square, an L-shaped stone marks the site of a 17th-century execution, where a priest was beheaded for killing a waitress who had offered him a rock-hard omelet. Across the square stands the town apothecary, which dates from 1422.