This Underrated European City Is One Rick Steves Calls A 'Rewarding Detour'

Rick Steves spends months each year in Europe exploring the entire continent to create itineraries and discover hidden gems to share with the world. Travelers who venture to the happiest region on Earth can venture off the beaten path for what Steves calls on his website a "rewarding detour" by visiting Tallinn, the capital of Estonia. If you're looking for a place that proudly wears its past and identity on its sleeve and where history comes alive during the summer nights, you'll be glad you ventured off the tourist track to visit one of Europe's smallest and most unique countries. In 2023, only 1.86 million international tourists visited the country; however, that figure is larger than Estonia's population.

Estonia's history and identity are deeply intertwined. The small country was repeatedly invaded by foreign armies since the Crusaders arrived in the 1200s, including the Danes, Teutons, Swedes, and the Russian empires. Later, during the Second World War, Estonia was occupied by the USSR and Nazi Germany and became a Soviet State afterward. Remarkably, in one generation after Estonia freed itself from the Soviet Union, it joined the European Union. All the while, Estonia deeply held on to its identity, including its unique culture and language, with both being sources of tremendous pride for locals and gateways into experiencing the country. You'll notice these walking around Tallinn, where medieval and Nordic roots meet innovation in the digital age. 

Steves notes that Tallinn is linked to Finland and Sweden by ferry and makes an easy side trip from Helsinki. Ferries take just over two hours from the Finnish capital, run multiple times a day, and start at €19 each way (about $22, as of this writing). If you'll be flying in, you'll arrive at Tallinn International Airport (TLL), with direct flights from all over Europe.

Whether you're visiting Tallinn during the famously long summer nights or strolling through the city's large Christmas market around the holiday season, you'll be fully immersed in the city's culture and charm in Old Town. Traditionally, Old Town was split into two different areas: Toompea, where the ruling class lived, and the Lower Old Town area below the hill. Up on the hill, you'll find Toompea Castle (and the Parliament building, the Riigikogu), both of which are open for free tours, though you should register beforehand. You'll also find two of the best areas to get a beautiful view of the city from the Piiskopi and Kohtuotsa overlooks — don't forget your cameras!

Down below in Vanalinn, the locals' name for the Old Town, spires and steeples sprout. Here, you'll find the city's picturesque Town Hall Square and rewarding hidden gems tucked in quiet alleyways, which Rick Steves recommends visiting during the morning or evening, when it's quieter. The Town Hall Square has stood at the heart of the city since the 1200s and has been the city's focal point since roughly 1400. Within a few years, the square also became home to what is now Europe's oldest continuously operating pharmacy. Venture inside and you'll find modern medicine, Klaret (a spiced wine), marzipan, and a Medieval medicine collection that features ingredients fit for a stereotypical witch's brew.

For a real trip back in time, visit the Kiek in de Kök Fortifications Museum. At the center, you'll find a former fortifications watchtower originally built in 1483 that survived being attacked by Ivan the Terrible. The museum complex brings together four different towers and historical exhibits about Tallinn during the late Middle Ages. While you're there, don't miss exploring the Bastion passages, a Tripadvisor Travelers' Choice attraction built and dug in the 1600s and 1700s.

Estonia's traditional food is as unique as its culture and history. If you're looking to mix all three together, consider one of the many medieval-themed restaurants around Old Town. Be transported back centuries as you dine on elk soup and ox sausages for less than €5 at Ill Draakon, or enjoy a full feast fit for a king at Olde Hansa. The restaurant uses ancient recipes to cook food as it would have been prepared in the Middle Ages, and you'll eat the same way. Prices start at €68 per person (there is a minimum of two people for the Grand Chef's Feast) for the dining experience. Both restaurants are highly regarded by visitors on Google Maps and Tripadvisor, who have praised the full experiences, from the food to the service. Rick Steves notes that you will likely be able to use English while dining out and exploring Tallinn, but locals will appreciate the effort to speak a few words of Estonian. He shares two key words you can use to win over locals' hearts: tänan (TAH-nahn), meaning "thank you," and terviseks (TEHR-vee-sehks), meaning "cheers!"

While Tallinn isn't as well known for its coffee culture as Vienna (or Paris or Rome), watching passersby while dining, enjoying a beer, or sipping a coffee al fresco on historic streets and soaking up the vibe are major draws. However, Tallinn's dark winter days average single digits of daylight. For warmer weather and longer days (bring an eye mask; summer days are 18-plus hours long), plan a visit in the late spring to early fall, between May and August. During this time, locals flock to the forests, the Baltic coast, and the breathtaking Estonian island of Saaremaa boasting uncrowded beaches.

If you're taking a quick detour to Tallinn, and you plan to visit major museums in Old Town or across the city, consider purchasing a Tallinn Card. The card provides unlimited access to over 50 museums and public transportation, including the Kiek in de Kök Fortifications Museum and the Bastion Passages; free public transportation and bicycle rentals; and discounts at certain cafes or restaurants during a 24-, 48-, or 72-hour period for a set price. Cards start at €43 for adults when bought online. Travelers who would rather not take a bus or public transportation can hop on Bolt e-scooters and are allowed to ride on sidewalks and bike lanes.

While Old Town Tallinn may look like a fairyland, hidden just outside of plain view are dark reminders of the past for many Estonians. If you're traveling to broaden your horizons, visit the Vabamu Museum of Occupations and Freedom, where Rick Steves notes you'll find insight into Estonia's past as part of the Russian Empire, under Nazi Germany, and as a Soviet Republic. Similarly, in the basement of an apartment on Pagari Street, you'll find a former KGB-run prison for political prisoners, now a museum. For a look into the KGB, don't miss visiting the former KGB listening post with a hotel facade, the Sokos Hotel Viru on the outskirts of Old Town. On the 23rd floor of the hotel, you'll find the base of operations, left half-trashed but fully preserved in the state it was in since the last KGB officer closed the door. If you'd rather leave the Iron Curtain in the past, you'll find plenty of charming and cute boutique hotels and hostels in the heart of Old Town to match your budget. Many start at less than $150 per night during the summer, with major discounts in the spring and fall months.