One of the most picturesque city centers I have ever had the pleasure of visiting wasn’t in one of Europe’s most popular destinations, but it certainly is catching the eye of history lovers and photographers alike. On my recent trip to Helsinki, I was presented with an opportunity to do a day trip to Tallin, Estonia – a medieval mecca where the city center boasts some of the most beautifully preserved architecture from the 13th to 16th centuries. The plan is that we would journey there by boat, have the day to explore, and be back in Helsinki in time for a late dinner. Not a bad gig!
So, I expected the ferry to be something similar to what we have here in the states – some semi-comfortable indoor seating, one or two bars/snack shops and that’s about it. Holy crap was I totally off-base!! The ferries over there are like mega cruise ships with a plethora of food options, comfy seating, shopping, and even a business lounge for those who would like a little more space and seclusion! We ended up taking the Megastar: Tallink Line, which got us from Helsinki to Tallin in 2 hours flat, first thing in the morning. By the time we hopped in an Uber to Old Town, we were ready to explore the windy historic streets!



One of the charms of Old Town is that many of the restaurants play to the old-timey feel you get walking through the streets. Initially, I was a little turned off by this because it felt super touristy, but when we sat down to lunch at Olde Hansa and grabbed a refreshing cinnamon beer (the most heavenly beverage of all time), our minds were quickly changed. Walking through the threshold of the restaurant is meant to transport you back to the 15th century; they served game meet like boar, bear, and elk – all which were super tasty by the way- and servers were dressed in period costumes. The service was also amazingly friendly, and they were quick to refill our chalices when the cinnamon beer was looking low. While this wasn’t initially a restaurant that I was particularly excited about, I walked out of there a convert!


The other cool thing about Old Town is that there are plenty of lookout points (better known there as “viewing platforms”) where you can really take in the entire city. On a bright sunny day, you may be jockeying for a prime spot to take a photo, but the wait for the perfect shot and views were totally worth it! A few of the popular ones are: Patkuli, Piiskopi, and Kohtuotsa – where the first photo in this post was taken.
Outside of the amazing views, if you find yourself in Tallinn, there are a few things that you have to check off the list before you leave; especially in Old Town:
- Make it to the Town Hall Square. The colorful buildings and inevitable live music (if the weather is nice) is worth spending some time. There are also a bunch of restaurants there – perfect for people watching.
- Visit Great Guild Hall. A standard example of medieval European architecture, this massive structure is not to be missed.
- Feel like royalty in the Danish King’s Garden. Lining the garden are the city walls, which are worth climbing up to catch some views when you’re done perusing the perennials.
- Tour the Bastion Passages. From the Danish King’s Garden you can go underground and check out tunnels that were used for all sorts of things, like bomb shelters in WWII, a place to move ammunition in the 17th and 18th centuries, and even where punk rockers found reprieve in the 80s.
If you are planning a day trip and looking to see as much as you can in one day, I highly suggest grabbing yourself a Tallinn Card. It gets you into most of the historical sites as well as a few other cool places worth visiting, like the zoo, Kadriorg Palace, and you can even join on a bicycle welcome tour.

In this post, I hardly scratched the surface of all that Tallinn has to offer, but hopefully this provides a good jumping off point if you’re looking to plan a day trip. Have any other must see spots in Tallinn? Be sure to let me know if the comments below :).
So pretty! So fun to visit somewhere off the beaten path.
Tallin is on my travel wishlist! In combination with Helsinki of course 🙂 Beautiful pictures ❤ It looks so enchanting!