Tall Hermann Tower: This tallest tower of the castle wall is a powerful symbol here. For 50 years, while Estonian flags were hidden in cellars, the Soviet flag flew from Tall Hermann. As the USSR was unraveling, the Estonians proudly and defiantly replaced the red Soviet flag here with their own black, white, and blue flag.
• Backtrack and go uphill, passing the Russian church on your right. Climb Toom-Kooli street to the...
 Dome Church (Toomkirik): Estonia is ostensibly Luth¬eran, but few Tallinners go to church. A recent Gallup Poll showed Estonia to be the least religious country in the EU—only 14 percent of the respondents stated that religion is an important part of their daily lives. Most churches double as concert venues or museums. Enter the Dome Church (free, Tue–Sun 9:00–17:00, closed Mon, www.eelk.ee/tallinna.toom). It’s a textbook example of simple Northern European Gothic, built in the 13th century during Danish rule, then rebuilt after a 1684 fire. Once the church of Tallinn’s wealthy, it’s littered with medieval coats of arms, each representing a rich merchant family and carved by local masters—the smaller the coat of arms, the older the family. The floor is paved with tombstones.
• Leaving the church, turn left. Pass the slanted tree and the big, green, former noblemen’s clubhouse on your right (vacated when Germans returned home in the 1930s), and go down cobbled Rahukohtu lane. Local businesses and embassies are moving their offices here and sprucing up the neighborhood. As you pass under the yellow Patkuli Vaateplats arch, notice a ramshackle bit of the 1980s surviving. Just a few years ago, the entire city looked like this. Belly up to the grand viewpoint.
 Patkuli Viewpoint: Survey the scene. On the far left, the Neoclassical facade of the executive branch of Estonia’s government enjoys the view. Below you, a bit of the old moat remains. The Group sign marks Tallinn’s tiny train station, and the clutter of stalls behind that is the rustic market. In the distance, ferries shuttle to and from Helsinki (just 50 miles away). Beyond the lower town’s medieval wall and towers stands the green spire of St. Olav’s Church, once 98 feet taller and, locals claim, the world’s tallest tower in 1492. Beyond that is the 985-foot-tall TV tower (much appreciated by Estonians for the heroics involved in keeping the people’s airwaves open during the harrowing days when they won independence from the USSR). During Soviet domination, Finnish TV was responsible for giving Estonians their only look at Western lifestyles. Imagine: In the 1980s, many locals had never seen a banana or pineapple—except on TV. People still talk of the day that Finland broadcast the soft-porn movie Emmanuelle. An historic migration of Estonians flocked from the countryside to Tallinn to get within rabbit-ear’s distance of Helsinki and see all that flesh on TV.
• Go back through the arch, turn immediately left down the narrow lane, turn right, take the first left, and pass through the trees to another viewpoint.
 Kohtuotsa Viewpoint: On the far left is the busy cruise port and the skinny white spire of the Church of the Holy Ghost; the spire to its right is the 16th-century Town Hall spire. On the far right is the tower of St. Nicholas’ Church. Visually trace Pikk street, Tallinn’s historic main drag, which winds through the Old Town, leading from Toompea down the hill (below you from right to left), through the gate tower, past the Church of the Holy Ghost (and Town Hall Square), and out to the harbor. The undesirable part of this city of 400,000 is the clutter of Soviet-era apartment blocks in the distant horizon. The nearest skyscraper (white) is Hotel Viru, in Soviet times the biggest hotel in the Baltics, and infamous as a clunky, dingy slumbermill. Locals joke that Hotel Viru was built from a new Soviet wonder material called “micro-concrete” (60 percent concrete, 40 percent microphones). To the left of Hotel Viru is the Rotermann Quarter, an industrial plant revamped into a new commercial zone. Our walk will end there.
• From the viewpoint, descend to the lower town. Go out and left down Kohtu, past the Finnish Embassy (on your left). Back at the Dome Church, the slanted tree points the way, left down Piiskopi (“Bishop’s Street”). At the onion domes, turn left again and follow the old wall down Pikk jalg (“Long Leg Street”) into the lower town. Wander back to Town Hall Square.
 Through Viru Gate, to Rotermann Quarter and End of Walk: Cross through the square (left of the Town Hall’s tower) and go downhill (passing the kitschy medieval Olde Hansa Restaurant, with its bonneted waitresses and merry men). Continue straight down Viru street toward Hotel Viru, the blocky white skyscraper in the distance. Viru street is old Tallinn’s busiest and kitschiest shopping street. Just past the strange and modern wood/glass/stone mall, Müürivahe street leads left along the old wall, called the “Sweater Wall.” This is a colorful and tempting gauntlet of women selling handmade knitwear (although anything with images and bright colors is likely machine-made). Beyond the sweaters, Katariina Käik, a lane with top-notch local artisan shops, leads left. Back on Viru street, the golden arches lead to the medieval arches—Viru Gate—that mark the end of old Tallinn. Outside the gates (at Viru 23), an arch leads into the Bastion Gardens, a tangle of antique, quilt, and sweater shops that delight shoppers, and the fine Apollo bookstore (with Internet access and a fine little café upstairs). Opposite Viru 23, above the flower stalls, is a small park on a piece of old bastion known as the Kissing Hill (come up here after dark and you’ll find out why).
Just beyond is Hotel Viru, the Viru Keskus shopping center (with a branch tourist information office, Internet café, supermarket in the basement, and laundry service), and the real world. For a look at today’s Tallinn, browse through the Rotermann Quarter. Sprawling between Hotel Viru and the port, this 19th-century industrial zone is now a much-hyped commercial district with office parks, fancy condos, department stores, and restaurants.