Estonia - Tallinn

 Cycle the Baltics 2026 - Estonia (Tallinn)

We left Calgary and flew to Frankfurt for a short layover before arriving in Tallinn, Estonia (country #59).  After what felt like approximately 47 hours in airports and airplane seats designed by medieval torture experts, we were very happy to finally reach our hotel.

Once settled, we had a quick nap before heading to the market for supper — a chicken shawarma salad bowl. Then it was back to the hotel room for cards, relaxing, and trying unsuccessfully to stay awake past 8:30 p.m.

The next morning, we headed out to explore Old Town. We started on foot and climbed up to Upper Town, or Toompea Hill, which has been the centre of political power in Estonia for centuries. From there, we had panoramic views over the red rooftops and church spires of the city below.

We explored Toompea Castle - home to Estonia’s parliament, and admired the striking Alexander Nevsky Cathedral - the Russian Orthodox church built during the Russian Empire’s rule over Estonia in the late 1800s. Its onion domes looked almost too perfect against the skyline.

After regrouping at the hotel, we rented bikes and attempted to navigate the lower town. In theory, this was a charming European cycling experience. In reality, riding bikes over medieval cobblestones felt like participating in a low-budget action movie while trying not to lose dental fillings.

Eventually we made it to Tallinn Town Hall Square, where restaurant patios were filled with people strategically facing outward so they could people-watch while eating. Honestly, it was elite-level lounging.

We passed Raeapteek, one of Europe’s oldest continuously operating pharmacies, dating back to 1422.  The buildings throughout Old Town were incredible, many dating from the 13th to 16th centuries. Tallinn’s Old Town is one of the best-preserved medieval cities in Europe and is designated as a UNESCO World Heritage Site. Walking through it genuinely felt like stepping into another century.

Unfortunately, the emergency dental surgery I had the day before leaving home was beginning to cause problems. I couldn’t even keep water down, so I headed back to the hotel to rest while Cathie went to explore the trendy Telliskivi Creative City market area, known for street art, cafés, shops, and creative spaces built into old industrial buildings.

When she returned, we headed back toward Old Town on foot. But first: ice cream. Priorities.  Cathie tried a chimney cake — dough wrapped into a cone and filled with pistachio cream, fresh fruit, cranberry brittle, and ice cream. With my stomach issues, I bravely attempted to keep down a single scoop of mango ice cream.

On this venture into Old Town, we followed Pikk Street, reportedly Tallinn’s first paved street and once an important route for merchants. The street led us to Fat Margaret tower and the old city walls, reminders that Tallinn was once a heavily fortified medieval port city.

We also visited St. Olaf's Church, which was believed to be the tallest building in the world in the 16th century. At one point its spire reached around 159 metres before repeated lightning strikes and fires forced several rebuilds.

We headed back to the hotel along the old city walls before meeting up with our cycling tour group for the next 11 days. The group then returned to Old Town for dinner — salad, chicken schnitzel, and cake. Unfortunately, I still couldn’t eat or drink anything at that stage, which was particularly cruel considering the cake situation.

Back at the hotel, I spent the night slowly sipping electrolytes and hoping hydration would win the battle.

The next morning, we returned to Old Town for a guided tour. Our guide, Lina, shared fascinating history about Estonia, the Baltic states, and life under Soviet rule. Estonia regained independence from the Soviet Union in 1991 and has since transformed itself into one of the most digitally advanced countries in the world — in fact Skype was invented here.

Off to cycle in the National park.