Short of time? You're in luck. Tallinn is a compact city, in which you can cover multiple sights without the need to travel far.
There are many historic and fun sights in the Old Town, which are very easy to access on foot and that you cannot miss. Still, Tallinn has a lot more to be discovered beside the Old Town. You should definitely spare some time to visit one of the other cool areas of Tallinn, like the green and beautiful or the trendy up-and-coming hipster suburb Kalamaja. Plan which you'd like to see, as you probably won't be able to make it to both in six hours.
Scale the City Wall
Many visitors of Tallinn arrive by ship. One of the first things you see coming from the sea are the towers of Tallinn’s Old Town - seeming like little red spikes lining the town. These landmarks are the remaining defensive towers and the city wall. They're also some of the coolest things in our town.
So, like any visitor to Tallinn's Old Town, you need to get past this wall first. There's no need to state your business these days, but it is easy to imagine armed guards up on the walls, looking down at you. The wall, originally almost 2.4 km in length and made of limestone, came with 8 gates, 46 towers, and an impressive moat. Now what is left of the moat camouflages as a pond in a park, but amazingly 1.9 km of the wall is still there, along with half of the towers.
Tallinn's City Wall is one of the best preserved in the whole northern European region and thus a must-see. So get up on it! Walk up on the wall and imagine all the wars that have involved Tallinn. There are several sections of the wall where you can climb up, for example at Hellemann Tower on Müürivahe street, or you can also visit three towers in quick succession: Nunna, Sauna and Kuldjala are all connected. However, the most famous section of the wall is in the Danish King's Garden and leads to the Maiden's Tower (part of the Kiek in de Kök Fortifications Museum). Be sure not to miss it! And following the narrow streets running behind the walls will bring a truly medieval feel to your walk.
Aside from the city wall's towers, there are tall, imposing church spires. Tallinn's skyline is so beautiful that no skyscraper is allowed ever to ruin it, there is even a law making sure of this, and ensuring nothing can be built higher than the highest church spire. St. Olav gets this honour, at 123.7 metres in height. Estonians are in general very private about their religion, though we do like to show off our old churches, and the Old Town has many to choose from.
Start with St. Olav's Church, the highest tower you can climb to get an unparalleled view of Tallinn that takes the breath away. Not far from St. Olav Church lies the Holy Spirit Church that housed the poor in medieval times and led the way to writing books in Estonian. A must-see is St. Nicholas' (Niguliste) Church, a building that was almost completely destroyed in the Second World War and now houses the Niguliste Museum, one of the branches of the Art Museum of Estonia.
The oldest church of all is to be found up on the hill: the Dome Church (also called as Cathedral of Saint Mary the Virgin) from the early 13th century; this church has seen its share of fighting and fire in the region but still nothing really compares to the beautiful coats of arms decorating the walls, never mind the view from the top of the tower. And finally, do not miss St. Alexander Nevsky Cathedral that stands imposingly over the old town, especially because admission is free.
Town Hall Square (Raekoja plats) is the heart and soul of the medieval Old Town. Frequently a sight for markets and concerts, if it's happening in the Old Town it's happening here. Summertime is filled with various events like Tallinn Old Town Days at the beginning of June, or Tallinn Medieval Days in early July. Every Wednesday from May to September there is a handicraft market to capture the imagination, so don't worry if you miss any of the special events.
Step into Europe's oldest continuously-working pharmacy (open since 1422) – Town Hall Pharmacy (Raeapteek), right on the square's corner. If you don't need any actual modern medicine, then take a look at the historic section, where they have recipes with burned hedgehog and human skull salt. They also sell traditional liquor that would certainly have been considered medicinal back in the day.
The main feature of the square is the Town Hall itself. Built in 1404, it's the only Gothic town hall in northern Europe. Now, look up! On top of the spire is the symbol of Tallinn - Old Thomas (Vana Toomas in Estonian). In summer you can also climb up the narrow steps of the tower to enjoy the view from the heart of the Old Town.
The true challenge, should you accept it, is to find a big round stone with arrows, somewhere on the square. If you stand on it and crane your neck you can find the five remaining medieval towers of the Old Town. Finding and naming them all is really fun!
The Old Town is perfect for getting lost in; even the locals end up having to turn round every now and again. The small alleys, courtyards, and winding side streets all make for a confusing but pretty mess, so enjoy it.
Go looking for the lovely St. Catherine's Passage (Katariina käik) with artisan shops and the Masters' Courtyard where local romantics go for hot chocolate even in the warm summer nights. Strike out for hidden antiques and design shops for that essential souvenir but avoid the overpriced amber-selling establishments (natural amber is rarely found in Estonia). Explore some interesting museums in the old town like the Estonian History Museum or the quirky NUKU Museum for Puppet Arts, which provides fun for children and adults alike.
When your feet are hurting from the cobblestone streets and museums then sit down for something to eat, away from the main streets and squares. The shortest street in the Old Town, Saiakang, has some cute cafes, while Rataskaevu street is a place where locals often go for a nice meal, and Vene and Müürivahe are two long streets that hide many good places for a bite to eat.
And if you get really lost then just stop someone and ask for directions. You can tell locals by the way they walk (faster than everyone else) and the way they look down or straight ahead, not up at the houses and towers.
Toompea aka the upper town is from where Estonia is ruled: both the parliament and the government are located up there. Toompea Castle houses the Estonian parliament - Riigikogu. Here are several houses wrapped together in history - the medieval crusader castle fuses with the early classical palace and hides the world's only expressionist-style parliament building in the courtyard. You can actually enter the Parliament building if you plan ahead, gain security clearance, and bring a passport.
Across the square, in front of the castle, is the St. Alexander Nevsky Russian Orthodox Cathedral. Step into this impressive sacred building, smell a hint of incense in the air and be dazzled by all the gold. The most historically-important church up there is not actually Nevsky, but the Dome Church, aka the Cathedral of Saint Mary the Virgin (also sometimes called Toomkirik). Don't let the sparse white walls of this Lutheran church put you off; the main interest is on the inside, as the church has seen more history than any other in Tallinn.
Finally, don't forget the viewing platforms! There are three platforms (Kohtuotsa, Patkuli and Piiskopi) overlooking the city with great photo opportunities. At Kohtuotsa you will also find a seagull called Steven walking on the edge of the platform posing for photos like a true supermodel. Those seagulls must be some of the most pictured birds out there... #Tallinnseagull and #Steventheseagull
Walk around beautiful Kadriorg or hipster Kalamaja
The Old Town is not everything in Tallinn; there is so much more to see. Take a small walk or a quick tram ride (hop on no. 3) to Kadriorg, perhaps the most beautiful area in Tallinn. In Kadriorg, you will find Peter the Great's gorgeous summer palace, built for his wife Catherine, that is now Kadriorg Art Museum. Kadriorg Palace, with its surrounding park, is already 300 years old and the park is the biggest one in Tallinn. As this museum is located right next to the President's Palace, you might be lucky enough to see the changing of the guards or the president herself.
There are also many other museums nearby, but most important of them all is Kumu. Kumu Art Museum houses an interesting and varied collection of Estonian art dating from the 18th century to the present day. This art museum is the perfect size in order to see everything in one trip.
If you are not that into art and are more of a nature lover, then just sit down on the grass, have a picnic and enjoy the day. Something delicious for your picnic can be found from local cafes like Katherinenthal, Gourmet Coffee, Dereku Burger or NOP, all of which bake and cook their dishes on the premises. You can easily follow the seaside back towards the port from Kadriorg if need be.
As an alternative, you can visit Kalamaja, the coolest area in Tallinn right now. Kalamaja consists of two sides: the industrial heritage left behind by the 20th century, and quaint wooden buildings that used to house the factory workers. Today many young families have made this area their home, so walking around Kalamaja gives you a good look at what is some of the most desirable housing in Tallinn.
The most popular area is Telliskivi Creative City. Telliskivi has turned an old industrial compound into studio spaces, creative companies' offices, cool restaurants, artsy coffee shops, and fancy beer bars specialising in local and international craft beer. Telliskivi Creative City, once considered a risky investment during the depths of the global recession, has since developed, matured and become a golden opportunity for innovative companies.
Don't miss out on some really cool street art decorating the houses and walls of the former factory. The Telliskivi area is quite big and something new always crops up, be it pop-up shops, galleries, or flea markets. This place is very close to the Old Town, just a short walk away, and gives tourists a view of the modern side of Tallinn, where old buildings become home to new ideas.