Tallinn, Estonia: A Ferry Ride Into History

Our Helsinki tour guide joked that when you search for tours of Helsinki, one of the first things that pops up is a tour of Tallinn, the capital of nearby Estonia.

So, naturally, off we adventured.

Tourists go to Tallinn for its remarkably preserved medieval Old Town. The Finns, apparently, have another motivation: they go for the booze. Alcohol is considerably cheaper in Estonia than in Finland, and according to our guide, some Finns arrive at Tallinn’s port and immediately board what amounts to a booze cruise, never venturing into the city at all. We thought she might be exaggerating. More on that later.

Tallinn is an easy day trip from Helsinki, and we made the two hour crossing with Eckerö Line. The ferry terminal was about a 15 minute drive from our hotel. Because we were leaving early, we took an Uber and returned by tram that evening. The terminal was a cavernous Nordic design statement: enormous, efficient, spotless and somehow stylish.

Boarding reminded us of ferries in Greece. Crowds gathered and surged forward, but the Finns and Estonians remained largely quiet and respectful, a welcome contrast to some of our more exuberant Mediterranean ferry experiences.

We spent an extra €48 for a private cabin, one of the smartest decisions of the day. Still jet lagged, we had a place to stretch out, nap and watch the Gulf of Finland slide past the window.

The ferry itself was surprisingly entertaining, with restaurants, cafés, shops, a casino and lounges. In one, a gentleman serenaded passengers with Peter, Paul and Mary’s “Blowin’ in the Wind,” which seemed appropriate as we crossed the Baltic. People drank coffee and alcohol and ate enormous breakfasts. Unlike some of the rough Greek ferries we have affectionately, or perhaps not so affectionately, called “vomit comets,” this ship sailed smoothly.

Two hours later, Tallinn appeared. And almost immediately, you understand why people come. Tallinn’s Old Town is one of Europe’s best preserved medieval cities. Much of its street plan and architecture dates from the 13th through 16th centuries, when the city, then known as Reval, prospered as a member of the Hanseatic League. The historic center is now a UNESCO World Heritage Site.

But Tallinn’s history is far more complicated than its towers and cobblestones suggest.

Estonia has been ruled by Danes, Germans, Swedes and Russians. It became part of the Russian Empire in the early 18th century, declared independence in 1918, was occupied by the Soviet Union in 1940, then by Nazi Germany during World War II, and then again by the Soviets. Estonia finally restored its independence in 1991 after the peaceful “Singing Revolution.” It joined NATO and the European Union in 2004.

That history made one of the first things we encountered especially poignant: the Russian Embassy, barricaded and surrounded by anti Russian and pro Ukrainian messages.

For Estonians, Russia’s invasion of Ukraine is not a distant geopolitical abstraction. Russia is next door, and memories of Soviet deportations, repression and forced Russification remain alive. The war has revived fears many Estonians hoped belonged to the past.

From there, we plunged into another occupying force: the tour groups. Two large cruise ships were in port, and their passengers seemed to have been disgorged simultaneously into the waiting arms of dozens of guides. Yet Tallinn absorbed them.

Like Helsinki, the city struck us as extraordinarily clean, particularly after our recent stay in London. Our Tallinn guide had just returned from London and made the same observation. She had been so surprised by the litter that she wanted to leave early.

At the heart of Tallinn is Town Hall Square, or Raekoja plats, the city’s commercial and civic center since the Middle Ages. Pastel colored merchant houses surround a broad cobblestone square dominated by the magnificent Gothic Town Hall. Markets have been held here for centuries, and Tallinn claims a public Christmas tree was erected here as early as 1441.

Rather than join one of the large groups, we hired a guide through GetYourGuide, our usual tour company. Our guide, Alex, was top notch. She pointed out the details that make walking tours worthwhile.

Just off the square is Raeapteek, first mentioned in 1422 and considered Europe’s oldest continuously operating pharmacy in its original premises. It has dispensed remedies for more than 600 years, although today’s prescriptions are considerably less imaginative than the medieval ones.

Alex explained that Tallinn’s architecture is a patchwork of its history: medieval merchant houses and Gothic churches alongside Baroque and Russian imperial buildings, Soviet structures and contemporary Nordic design.

Even the Town Hall offered a glimpse into medieval social control. Alex pointed out the metal rings associated with public punishment and shame, where offenders could be chained for the community to see. Apparently a woman could find herself there for such transgressions as talking too much. Thankfully, times have changed.

We were disappointed to learn that the Town Hall had closed for the season just days before our visit. It is generally open from June through August, and we arrived in early September.

From there, we essentially walked through 800 years of history. Medieval walls and towers recall the wealthy Hanseatic trading city. Russian rule left Orthodox churches and imperial buildings. Estonia’s brief period of independence between the world wars added another layer, while Soviet rule brought apartment blocks, monumental public buildings and modernism.

From the number of magnificent churches, you might assume Estonia remains deeply religious. It doesn’t.

Estonia became predominantly Lutheran after the Reformation, but decades of Soviet atheism transformed religious life. Today it is one of Europe’s more secular societies. Many historic churches survive primarily as cultural landmarks, museums and concert spaces.

When we asked Alex what Estonians think about the Soviet decades, her answer was wonderfully honest: “Ask ten Estonians and you’ll get ten answers.”

Some remember occupation, censorship, deportations and repression with bitterness. Others, particularly those whose memories involve childhood, work or stability, can be surprisingly nostalgic. History becomes more complicated when the people who lived through it are still around to tell the story.

One curious legacy of Soviet rule was the 1980 Moscow Olympics. Tallinn was chosen to host the Olympic sailing regatta, and Moscow suddenly needed this Baltic outpost to look presentable to the world. A construction boom followed, producing the Pirita Olympic Yachting Centre, Hotel Olümpia, Linnahall and the Tallinn TV Tower, along with improvements to the airport, roads and waterfront. The Soviets had inadvertently helped modernize the city that, eleven years later, would celebrate escaping Soviet rule.

Today Estonia faces a very different challenge. There simply aren’t very many Estonians.

The entire country has about 1.36 million people, and the population is shrinking. Births are far below deaths, and more people have recently been leaving than arriving. The government has responded with generous parental benefits, lengthy paid leave and child allowances. But money alone does not solve the problem.

Young Estonians are educated, mobile and European. Some can earn more elsewhere. Others simply want the adventure of living in London, Berlin or Stockholm. At the same time, the economic disruption following Russia’s invasion of Ukraine has made life considerably more expensive.

It is one of modern Estonia’s paradoxes. Since regaining independence, this tiny country has become one of Europe’s most technologically advanced and digitally connected societies, yet it must still persuade its young people to stay, build careers and raise families there.

By late afternoon, our introduction to Tallinn was over.

We headed toward the ferry terminal with the stream of Finns and Estonians returning to Helsinki.

And then we saw them: Young people. Old people. Couples. Groups of friends. All carrying boxes, shopping bags and rolling carts filled with bottles of alcohol. Apparently our Helsinki guide had not been exaggerating.

We boarded, found our cabin and settled in for the two hour ride across the Gulf of Finland.

Tallinn had surprised us. We expected a beautiful medieval city, and it delivered. But what stayed with us was something deeper: a place whose buildings and people have survived centuries of foreign rulers, occupations, wars and political systems.

Today Estonia again finds itself at a geopolitical crossroads, with Russia on its border, war nearby and demographic challenges at home. Yet Tallinn hardly feels like a city looking backward. If history has taught Estonians anything, it is how to adapt.

Our bet is that these lovely people and this lovely city will do what they have done for 800 years: adjust, endure and ultimately thrive.