Medieval Tallinn is a fairy tale of narrow walkways, alleys, winding cobbled streets, tower ramparts, church spires and 14th-century buildings. Kept effectively hidden from the eyes of the West for more than half a century, it has finally reappeared as one of the most picturesque and best preserved medieval cities in Europe.
Surrounded by 2.5kms stretch of defensive walls, most of which are still intact, Tallinn's lower town revolves around the Town Hall square named Raekoja plats. From here, Viru street, today a pedestrianised shopping mall and the centre of Tallinn life runs east towards Viru gate. This simple medieval structure, partly hidden by dense foliage is one of the six former gates which were once used as the entrances to the lower town.
Vene street leads roughly northeast past a cluster of tiny craft shops and numerous medieval courtyards. Pikk street which like Viru and Vene emerges out of Raekoja plats runs north towards the Great Coast gate and the Paks Margareeta, a round 16th-century thick-walled bastion which formerly protected this entrance to the Old Town.
While walking along Pikk, don't fail to inspect the splendidly restored medieval houses that line both sides of this particular walkway. Of special mention for their architectural beauty are the red-roofed corner building at Pikk 4 and the huge green and white elaborate structure at Pikk 26. The buildings at Pikk 17 and Pikk 20 are valuable more for their historical significance than for their architectural beauty. The former which is now occupied by the Estonian History Museum was owned in the past by the Great Guild, an association to which important 15th-century tradesmen once belonged. The latter which is externally adorned with statues of Martin Luther and St.Canutus was owned for several centuries by a German association of master artisans and craftsmen.
Walking further north along Pikk, you will finally reach the 11th-century Oleviste Church. There's nothing interesting inside but its 120 metres high tower is one of Tallinn's most important landmarks.
From the lower town, the easiest way to reach Toompea Hill is from the west end of Pikk street where the Pikk Jalg tower dominates the picture. If you continue straight ahead along Pikk Jalg, you'll soon reach Lossi plats, the beautiful square on Toompea dominated by Alexander Nevsky Cathedral on one side and Parliament House on the other. Both meticulously restored to their former grandeur about five years ago, they look wonderful, although their architectural styles are contrasting. The Russian Orthodox multi-domed Cathedral has typical Russian-style architecture while the pink-coated Parliament has a simpler classical exterior.
Next to Parliament House, you can still see three of the four corner towers built by the Knights of the Sword in the late 13th century.
Continue north on Toompea past Toomkirik, Estonia's oldest church, until you reach one of the three lookout points that overlook the lower town. One such lookout point is next to a restaurant that has tables outside, from where you can enjoy a superb view while taking a drink or a snack. The gorgeous view from any lookout point reaches as far as the harbour and the ferry terminals. Don't forget to bring a camera along with you to take aerial photos of the medieval red-roofed buildings and the round defensive towers that line Lai, Pikk, Uus and Aia streets in the lower town.