Wheel Well: The well is named for the “high-tech” wheel, a marvel that made fetching water easier. Most of the Old Town’s buildings are truly old, dating from the 15th- and 16th-century boom-time. Decrepit before the 1991 fall of the USSR, Tallinn is now more affluent and has been quickly revitalized.
• Turn left on Rüütli street and walk two blocks to...
 St. Nicholas’ (Niguliste) Church: This 13th-century Gothic church-turned-art-museum served the German merchants and knights that lived in this neighborhood 500 years ago. The Russians bombed it in World War II: In one terrible night, on March 9, 1944, Tallinn was hit, and the area around this church—once a charming district, dense with medieval buildings—was flattened (35 kr, Wed–Sun 10:00–17:00, closed Mon–Tue; organ concerts Sat and Sun at 16:00).
• From the church, turn right and climb the steep, cobbled, Lühike jalg (“Short Leg Lane”). It’s lined with quality Estonian craft shops. At the gate, notice the original oak door, one of two gates through the wall separating the two cities. This passage is still the ritual meeting point of the mayor and prime minister whenever there is an important agreement between town and country. Don’t go through the gate, but continue straight into the view courtyard. Then climb right toward the Russian Cathedral for a good view of the wall.
 Danish King’s Garden: Stand in the former garden of the Danish king. The imposing city wall once had 46 towers—the stout, round tower way ahead is nicknamed “Kiek in de Kök.” (While fun to say, it means “Peek in the Kitchen.”) It was situated so that “peek” is exactly what guards could do. (It’s now a small museum with cannons.)
Tallinn is famous among Danes as the birthplace of their flag. According to legend, the Danes were losing a battle here. Suddenly, a white cross fell from heaven and landed in a pool of blood. The Danes were inspired and went on to win. To this day, their flag is a white cross on a red background.
• Walk to the entrance of the onion-domed Russian Cathedral facing the pink palace.
 Russian Cathedral and Toompea Castle: The Alexander Nevsky Cathedral was built here in 1900 over the supposed grave of a legendary Estonian hero—Kalevipoeg. While it’s a beautiful building, most Estonians don’t like this church. Built to face the national parliament, it was a crass attempt to flex Russian cultural muscles during a period of Estonian national revival. Step inside for a whiff of Russian Orthodoxy; about a third of Tallinn’s population is ethnic Russian (church free and open daily 8:00–19:00).
Cross the street to the pink palace—an 18th-century addition that Russia built onto the Toompea Castle. Today, it’s the Estonian Parliament building, flying the Estonian flag—the flag of both the first (1918–1940) and second (1991–present) Estonian republics. (Locals say they were always independent...just occupied—first by the Soviets, then by the Nazis, and then again by the USSR.) Notice the Estonian seal: three lions for three great battles in Estonian history, and oak leaves for strength and stubbornness. Ancient pagan Estonians, who believed spirits lived in oak trees, would walk through forests of oak to toughen up. (To this day, Estonian cemeteries are in forests. Keeping some of their pagan sensibilities, they believe the spirits of their departed loved ones live on in the trees.)
• Step left across the parking lot, around the palace, and into the park to see the...