I truly believe if you Google the word charm, pictures of Tallinn, Estonia will appear. The jewel of a city on the Baltic Sea is a delight, with a fairy-tale castle, sidewalk musicians and some of the most delicious chocolate anywhere.

It was a bright, sunny morning as we sailed into the Tallinn harbor. After three intensive days touring Russia, we were looking forward to the chance to wander without an itinerary. The ship’s shuttle dropped us off near the entrance to Old Town, and as we stepped inside the medieval city, we were instantly smitten.

Arriving at the Tallinn Harbor.
Old Town2
First view of Old Town.
Flower Market
Old Town Flower Market.

We started our walk in Lower Town and slowly made our way toward Toompea Hill and Upper Town.

Sidewalks with handrails could be found beside many of the narrow cobblestone streets and steep hills.

We took a quick walk through the grand Alexander Nevsky Cathedral, with domes modeled after St. Basil’s in Moscow. The cathedral was built in the late 1800s when Estonia was part of the Russian Empire.



At the top of Toompea Hill is Toompea Castle, a ninth century fortress that houses the Parliament of Estonia and is the city’s top viewing destination.

Castle Herb
Herb in front of the entrance to Toompea Castle.
Castle Me1
From the top of the Castle, Old Town stretches out to the sea in one direction…
View New
…and the new part of the city stretches out in the other direction.

We headed back to Lower Town in search of a restaurant I had wanted to try for lunch. After all the Russian fare, we were craving a little taste of Italy! The charming Pulcinella was started by a family from Naples and is tucked away on a street called Suur-Karja. Inside are cozy tables in several wine cellar-like rooms.


After lunch, we walked back through the town square and looked for our next food destination, coffee and dessert at The Pierre Chocolaterie, a small café nestled in a courtyard called Meistrite Hoov.  (Tea & Coffee Shops Around the World.) The charming Meistrite Hoov – Masters’ Courtyard – is worth a look even if you don’t stop for a coffee.

Meistrite Hoov

The Pierre Chocolaterie’s  lovely courtyard is a wonderful spot for a coffee break.

The sounds of street musicians could be heard as we made our way through Tallinn’s Old Town. The music was happy and gave a festive air to the day. None, however, captured the crowds and won us over as much as these four very earnest “Beatles.”

Before heading back to the shuttle, we tracked down the Kalev Chocolate Factory Store. Tucked away in a corner of the Rotermann Quarter Courtyard, it’s about a 15 minute walk from Old Town. Kalev’s gorgeous gift boxes are as fabulous as the chocolates inside, and the prices at the factory are substantially lower than we found at other shops in town and at the port. Our only regret was not picking up a gift box for ourselves!

Candy Factory


  • I’m so impressed that you took the time to blog your day while on the cruise. I’d like to do the same on the cruise, because if I don’t I know it probably won’t get done. What program or app did you use? Did you record your thoughts and pictures on iPhone or iPad?
    I look forward to reading the rest of your postcards and to hearing from you.

    Susan Fryrear
    Louisville, Ky

  • Susan, thank you so much for your kind comments! I actually wrote the blog when we returned from the trip. I keep a notebook when traveling and then pull everything together, edit photos and organize my thoughts once I’m back home. I take most of my photos with a Nikon D5500 camera/18-140mm lens and use my iPhone as a back-up and for quick shots in places like cafés. The website is set up through WordPress and hosted by Bluehost. Many thanks for reading, and best of luck in your blogging endeavors! Have a wonderful time on your cruise!

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