Tallinn, Estonia’s capital city, welcomes visitors to experience its medieval charm and modern high-tech energy. More than a third of Estonia’s population of 1.3 million call Tallinn “home”.
Immersing ourselves in this city’s charm was a true joy for my husband and me. With so much variety and so many things to do, we managed to fill three days with unforgettable experiences.
Tallinn Highlights:
- Visiting Tallinn for the first time? I highly recommend beginning with a walking tour to familiarize yourself with Tallinn’s Old Town, its compact layout and historic city walls.
- Having explored both the haunting KGB prison cells and the interactive Seaplane Harbour Museum, I provide a balanced look at Tallinn’s somber past and maritime future.
- Using a Tallinn Card (compliments of Visit Tallinn), we took in a number of the city’s best attractions and freely availed ourselves of its reliable public transit system.
Editor’s note: The writer was hosted.
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Delve Into Tallinn’s Fascinating History in Old Town

Old Town, a compact area of Tallinn, is a UNESCO World Heritage Site that surprises and captivates visitors with its historical structures, colorful architecture, intriguing shops and quaint eateries.
- Enjoy panoramic views. Climb and walk along the city wall for sweeping views of church spires and red-tiled roofs.
- Visit Medieval Town Hall Square. This is where (according to popular belief) the world’s first public Christmas tree made its appearance.
- Spend some time at Tallinn Town Hall. This remarkable 13th-century building is the only intact Gothic town hall in Northern Europe. We toured the building, then made our way up the tower, where the view of the city and the Baltic beyond made us forget all the stairs we climbed.
- Drop into the World’s Oldest Operating Pharmacy, which has occupied the same yellow building since 1422. It smelled like a pharmacy, but felt like a piece of history. If you’re looking for something a little different, try the ‘love potion’, consisting of a piece of marzipan with an almond on top. It was smile-worthy, but after nearly fifty years of marriage, we didn’t need the magic or the calories.
- Ascend Toompea. This is flat-as-a-pancake Estonia’s only mountain. The views of lower Old Town definitely made the stairs we had to climb worth the effort.

SheBuysTravel Tip: Before descending the mountain, be sure to visit Toompea Castle, Estonia’s parliament and Alexander Nevsky Cathedral
Experience the Tragedy of Occupation Through the Voices of Those Who Survived

- Vabamu Museum of Occupations and Freedom: Delving into Estonia’s tragic stories of occupation was sobering and difficult. The heart-wrenching personal accounts of Estonians who survived the horrors were stark, unpolished reminders of evil in its rawest form. Despite our prior knowledge of Estonia’s history under occupation, the experience shook us to the core.
- KGB prison cells: Located in the basement of a luxury apartment building, the KGB prison cells tell the story of one of the darkest chapters in Estonia’s history. In this Soviet pre-trial detention center, authorities held Estonian citizens of all ages, genders and walks of life under deplorable conditions. Their cruel captors tortured them and sentenced them to prison, deportation or death. Once again, we were deeply moved by the decades-long suffering of the Estonian People.
- The Memorial to the Victims of Communism is not in the Old Town but provides a compelling record of the names of thousands of Estonians who disappeared without any knowledge of their ultimate fate.

SheBuysTravel Tip: I won’t sugarcoat it: the experiences are heavy on the heart. But you can’t truly understand Estonia without seeing this side of its history.
On the Lighter Side

- Seaplane Harbour Museum: An enormous hangar houses the unique, interactive Seaplane Harbour Museum, which presents Estonia’s maritime history. The impressive collection includes seaplanes, ships, artifacts and a 1930s submarine that visitors can tour. We went for an hour and ended up staying for more than two hours.
- Tallinn TV Tower Observation Deck: When you stand on the observation deck of Tallinn’s TV Tower at 557 feet, you will be treated to a breathtaking panoramic view of Estonia’s capital city and beyond.
- Estonian History Museum: This museum is scattered over several locations in Tallinn. The variety and scope of exhibits can keep a history buff busy for an entire day or more. Part of the Estonian History Museum is the 15th-century Great Guild Hall, a Gothic-style building where you never know what you’ll find inside on any given day. During our visit, we had the opportunity to browse a captivating exhibit of international bookbinding art.
Discover Tallinn’s Vibrant and Varied Food Scene
The food of Tallinn is homey and full of flavor. Estonians throughout the country make excellent use of the foods available from land and sea. Here are some ideas to tempt your taste buds:
- Olde Hansa: Step into the past and dine with wealthy merchants during the Hanseatic era in a medieval-style dining room. Savor dishes from 700-year-old recipes as you listen to roving troubadours
- Põhjala: Raise a glass at the first and largest craft brewery in the Baltic states. Enjoy traditional and creative sips to wash down some of the brewery’s savory bites.
- The Market in Old Town: This spacious market is the place to go if you want to find something special at a reasonable price. Along with stalls of produce, meat, fish and baked goods, you’ll find street food from a variety of nationalities. The aromas from the food stalls were intoxicating, and the possibilities were endless. We settled on an Uzbekistan stall and enjoyed every mouthful of our savory soup and shared savory pastry.
Where to Find Some Relaxing Downtime

Tallinn has accommodations to fit every need and budget. We stayed at Hestia Hotel Barons in Old Town. Clean, comfortable and reasonably priced, this charming boutique hotel was the perfect retreat after a day of sightseeing.
Estonia’s capital is a safe and walkable city with excellent public transportation, but our location puts everything within walking distance. Wherever you decide to lay your head at the end of the day, I recommend considering your activities and adding a convenient location to your list of must-haves.
FAQ: Planning Your Trip to Tallinn
Absolutely. Tallinn is consistently ranked as one of Europe’s safest capitals. The Old Town is well-lit and frequently patrolled. However, the medieval cobblestones can be uneven and slippery when wet, so sturdy, slip-resistant walking shoes are a must. Even with my sensible shoes, I came close to twisting an ankle more than once. So step carefully.
Yes, it provides free access to over 50 museums (including the TV Tower and Seaplane Harbour) and unlimited public transport. The Tallinn Card is particularly valuable if you plan to visit more than three major attractions in 48 hours. Between the places we visited and all the buses and trams we rode, we could see that the card was well worth the $73 price for 48 hours.
Steep streets connect the Upper Town (Toompea) and Lower Town. While beautiful, the incline and cobblestones can be challenging. If you have mobility concerns, consider taking a taxi from the main square to the top of Toompea.
Not at all. While the older generation may speak more Russian or German, younger Estonians and almost everyone in the tourism industry speak excellent English. We found that learning a few simple words, such as Tere (Hello) and Aitäh (Thank you), will often earn you a smile.
Estonia is a highly digital society. Credit and debit cards (Visa/Mastercard) are accepted almost everywhere, including cafes and the market. We didn’t feel the need to carry a lot of cash, but we made sure we had a few Euros for small purchases.


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