Private Shore Excursion: Highlights of Tallinn with Kadriorg and Pirita

Toompea's dominating landmark is the Russian Orthodox cathedral named for the duke who attacked southeastern Estonia and Pskov in the early 13th century. Tsar Alexander III ordered the cathedral designed in 1894 by St. Petersburg master Mikhail Preobrazhensky and it was completed in 1900. According to legend, the cathedral was built on the grave of Estonian hero Kalev and has suffered structurally as a result.

The oldest sections of Tallinn's city wall were built in the 13th century. During the next three centuries, it became one of the largest and strongest defence systems in the entire Northern Europe. More than a half of the magnificent defence system has been preserved as a city wall - this includes 1.85 km of the wall, 26 defence towers, 2 gates and fragments of two front gates. Patkuli viewing platform is a good place for examining the city wall, and a number of towers are open for visitors.

One of the oldest continuously running pharmacies in Europe is on Town Hall Square. No one knows exactly when it opened, but records show that the Raeapteek was already on its third owner in 1422. In medieval times patients could buy mummy juice and burnt bees for treatment, and healthy folks could even drop in for a glass of spiced wine. Keeping up with the times, the pharmacy sells the usual aspirin and condoms, but part of the shop is also a museum, displaying old medical instruments and other curiosities.

If there’s one part of Tallinn outside Old Town that a first time visitor absolutely, definitely, unquestionably has to see, it’s Kadriorg. Though it’s only a few minutes’ walk from the centre, this quiet area is a world unto itself, a secluded neighbourhood made up of large areas of forested park criss-crossed by paths and dotted with statues and ponds. It’s also home to a number of intriguing 19th- and 20th-century villas, and the nation’s top art museums.

Winning the title 'European Museum of the Year 2008' , Estonia's largest art museum makes its home in this enormous, cutting-edge facility built into a limestone cliff in Kadriorg. It serves as both a national gallery, displaying treasured works from Estonia's past, and as a contemporary art gallery, showing the latest trends. While here, be sure to explore the fascinating complex, built by Finnish architect Pekka Vapaavuori.

Twisting cobblestone lanes and iron street lamps. Gothic spires and medieval markets. Cappuccino and Wi-Fi. This is the city's famous Old Town. If you're looking for that mix of historic ambience and cutting-edge culture that defines Tallinn, you'll find it here. Built up from the 13th to 16th centuries, when Tallinn – or Reval as it was known then – was a thriving member of the Hanseatic trade league, this enclosed neighbourhood of colourful, gabled houses, half-hidden courtyards and grandiose churches is, quite rightly, the city's biggest tourist draw. And the fact that it's all neatly packaged within a mostly-intact city wall and dotted with guard towers gives it an extra dose of fairytale charm. It’s small, compact, and very easily explored on foot.

The Regatta of Moscow 1980th Olympics was organized in Tallinn. A special Regatta complex was built on Pirita Beach to accommodate participants. The colors of the complex reflect the natural landscape of the area, mixing it with the environment.

The Estonian Parliament building is located next to the walls of Toompea Castle. This is an active government building, open for tourists to observe the work of Parliament from a special balcony. The Tall Hermann Tower (Pikk Herman) is part of the Parliament building. This is the highest tower of the Tallinn city walls.

For a few years during Estonia's first period of independence (1918 - 1940), the Estonian head of state worked out of the Kadriorg Palace, but in 1938, this purpose-built presidential palace was opened next to it, just up the hill. The Presidential Palace's style echoes the Kadriorg, albeit without quite so much flourish. Since the building once again serves as the President's office and residence, it's closed to visitors.

St. Olaf's 124m spire is a Tallinn landmark, and was the tallest building in Europe between 1549 and 1625. An old legend claims that the church was built to attract more merchant ships to the town by a mysterious craftsman who promised to work for free if the townspeople discovered his name (Olev). In reality, the church took its name from the canonised Norwegian king, Olav Havaldsson. The first mention of the church dates to 1267, but the interior dates to 1840 and reflects that era's Historicist bent.

Completed in 1960, Tallinn's Song Festival Grounds were the first modern post-war construction to be built in the city. Unique in Europe, they were designed by Alar Kotli, Henno Sepmann and Uno Tölpus. Their design took into account the nature of the land they were to be built on: audiences would be seated on the slope of the hill, so the song arch would need to echo sound to them. A copy of the song stage was later erected in Vilnius.

Lower Town, the larger part of medieval Tallinn (or Reval as it was called back then), became a member of the Hanseatic League at the end of the 13th century. Goods from around the world came in through the port and were traded on the market on Town Hall Square. Reval operated autonomously from the rest of the Estonian territories right up until Tsarist Russian times. As in the rest of the country, the real movers and shakers in Reval society were the Baltic Germans, with Ethnic Estonians for most part second-class citizens. However, Estonian peasants from surrounding areas often escaped to the city, where they could eventually be considered free.

Built on the spot where the ancient Estonians' wooden fortress stood before the 1219 Danish invasion, Tallinn's castle served for seven centuries as the seat of power for the nation's foreign masters. Now it houses the Riigikogu, Estonia’s parliament. On one corner of the castle you can see Pikk Hermann tower with the blue, black and white tricolour flag waving above it. It’s commonly recognised that whoever’s flag flies on top of this tower is the ruler of Estonia. The pink section you see in front is actually a baroque structure added in the 18th Century.