Explore Tallinn in 24 hours
Tallinn is an easy day trip via ferry from Helsinki, Finland. The Tallink Group runs a ferry about every 2 hours throughout the day, and a roundtrip ticket will cost you roughly 50 Euros depending on which ferry time and if it is a same day ticket versus two seperate travel days. While Tallinn could easily be seen on a day trip, I believe it deserves, at the very least, an overnight exploration.
Tallinn is a dichotomy of time periods, and each is well represented by various neighborhoods, all of which are worth a visit. I visited in the winter and completely fell in love with the city. I stayed in Old Town at one of the nicest hotels in the country, and I was treated like royalty. The quality of service I received was excellent, and despite the 5 star hotel rating, the prices for accomodation and food were very affordable compared to what I would have paid in Western Europe or the USA for the same. The Christmas lights were still up around the city, and snow was lightly falling throughout my stay. It was uncrowded, quiet, cozy, a bit mysterious, and definitely romantic.
Old Town dates back to the 13th Century, and it is a well preserved representation of Medieval and Hanseatic Estonia. Besides historic structures, you'll find an endless supply of interesting, quirky, and charming cafes and restaurants tucked away in random cellars. Seriously, if you don't climb down a steep staircase into a cellar at some point, I doubt you explored the city to its full. If you can stay in Old Town, you should. The area is extremely walkable, and the other neighborhoods are easily accessible by a cheap Uber ride. I did not try out the public transit while I was there, but you'll have to walk to the edge of Old Town to catch a bus as they don't drive through the Medieval heart of the city.
The areas around Old Town tend to be a combination of pre-Soviet Estonia, especially just south and east of Old Town, Soviet Estonia, and Modern Estonia. Balti Jaama Turg ("Baltic Station Market") and Telliskivi Loomelinnak ("Telliskivi Creative City") are neighborhoods just northwest of Old Town, and are a great example of post-Soviet, modern (and slightly hipster) Estonia.
The list below is comprised of historic and tourist sites, a variety of cafes, restaurants, and bars, as well as a couple of parks, all in various neighborhoods of the city. Extensive research, local recommendations, and first hand experience helped me formulate my recommendations.
I hope you enjoy your visit to Tallinn as much as I did mine. Personally, I can't wait to visit again in the spring or summer when the city is really alive.
