Tallinn has been on my radar for over a decade, ever since I first read about this beautifully preserved medieval city. Founded in the mid-13th century, and located on the Gulf of Finland, it is a great place to spend a weekend if you happen to be in the neighborhood on a tour of the Baltic States, or on your way to or from Russia (our case).  Fun fact: Skype was founded here which is one example of how this medieval city is most modern as well!

We stayed at the charming Three Sisters Hotel located on Pikk Street, the merchants’ main thoroughfare,  just inside city walls near Fat Margaret’s Tower (no relation) and the harbor.  Three 14th century merchants’ homes were combined and renovated before opening as a hotel in 2003. The rooms retain a medieval feel while providing all the modern conveniences.  It is a great base for exploring the city, which is easily and best explored on foot.

There are an impressive number of elegant churches including St. Olav’s Church whose history dates to the 12th century with written records existing from 1267. There is an observation deck that can be accessed via a winding rickety staircase (not for the faint of heart and not to worry – there are other great vista points on Cathedral Hill).

The Town Hall recently celebrated its 600th birthday, although it was built on the foundations of a mid-13th century predecessor.  As a Hanseatic city, Tallinn controlled eastern trade and became quite prosperous with its golden age extending into the 16th century. The wealth of buildings still remaining from that era attest to the skill of the craftsman and the durability of the local limestone.

Way atop the Town Hall spire, Old Thomas  the weathervane serves as protector and symbol of Tallinn, as well as providing weather info!

Until the late 19th century, Tallinn was divided feuding towns:  Toompea or “Cathedral Hill” — seat of central authority and  where the nobility lived — and lower town that was the center of trade and “city of the citizens.” The two areas remain distinct today and are connected by  Short Leg and Long Leg lanes. Ascending the hill, there are excellent views across the old town including the one above featuring St. Nicholas, formerly a church and now a branch of the Art Museum of Estonia.

At the center of Toompea stands the 13th century  St. Mary’s Cathedral , the oldest church in Tallinn and mainland Estonia and the only building to survive the devastating 17th century fire that destroyed the rest of Toompea. Also in the neighborhood, the Estonian Parliament, many coffee shops and galleries, and several embassies.

Be sure to check out the terraces on Toompea Hill that providing wonderful panoramic  views! On a clear day you can see Finland across the gulf.

Much of the old town’s original fortifications remain and the main gates continue to function as entrances.  You can access the ramparts and imagine what life might have been back in the day.

If you are Tallinn bound,  I highly recommend A Walking Tour of Tallinn by Rick Steves. (Too late for me–I only just came across it while working on this post.) He covers all the highlights and does an excellent job pointing out the sites and their history.  See also FoodieFriday | Tallinn, Estonia for some advice on what and where to eat.  Lastly, we enjoyed the services of Estonian native Aare Neerut, whose local Tour Service Agency  arranges transport and guides as well for those who want to go further afield.