Spend the morning getting familiar with some of Tallinn’s less conventional landmarks. We’ll see the looming Patarei Prison—a seaside penitentiary disused since 2002, and now featuring a museum about the victims of Communism—as well as Linnahall, a sprawling Brutalist building complex and one of Tallinn’s most imposing Soviet souvenirs. We’ll eat lunch in Kalamaja, a picturesque district of old-style wooden houses, before heading out of town in the afternoon to see Rummu Quarry, the flooded remains of a former forced labour camp.

Today we’ll leave Tallinn, driving east—but not without first stopping at the striking Maarjamäe Memorial Complex, built to remember the victims of World War II. From there, we’ll drive to Sillamäe. A former secret city during the Soviet period, when the chief local industry was uranium extraction, Sillamäe is now open to visitors and makes for a fascinating (and surprisingly quaint) stop along our journey. Finally we’ll arrive in Narva, a border town where Russia and Estonia are divided by a single river. Here we can see the local Lenin monument, the last in Estonia and one of the last still standing in the EU, before having dinner at the waterfront.

Leaving Narva behind, we’ll follow the border south along Lake Peipsi, the fifth-largest lake in Europe—first to Mustvee, where we’ll learn about the local community of Russian Old Believers, a splinter sect of Orthodox Christians who have been settled in this region for many generations. We’ll spend the night a little further south, in Tartu. Tartu is a lively place, a college town with a delightfully bohemian vibe. After getting settled into our hotel, we’ll take a short walking tour followed by some free time to explore. In the evening, we’ll meet back up for dinner at an iconic local restaurant situated inside a former gunpowder vault.

As we cross from Estonia into Latvia today, we’ll visit a number of this region’s Soviet-era memorial sites. We’ll stop at a waterside World War II memorial park in Tartu, then visit a memorial to the socialist revolutionaries of Valga. We’ll drive on to Līgatne, in Latvia—a stunning little village built around the local paper mill. Here we’ll take a tour of an extensive fallout shelter built during the Cold War period, before settling for dinner, then later retiring to our accommodation in some of Līgatne’s picturesque wooden cottages.

From Līgatne, it’s just an hour to the Latvian capital of Riga. Stopping first to see the powerful sculptures at the Salaspils Memorial Park en route, we’ll spend the rest of the day exploring Riga. From modern architecture to historic German mausoleums, and from picturesque church spires to colorful, chaotic, open-air markets, get ready to explore the Latvian capital and all its unique charm. To cap off the day, we’ll visit one of Riga’s best up-and-coming breweries for a gastronomic tour through the menu. 

Crossing to the west coast of Latvia, we’ll visit the abandoned Northern Forts—the dramatic, sea-blasted ruins of an imperial naval defense system. From there we’ll drive into Karosta, once a closed, high-security naval district, where Khrushchev-era housing blocks rub shoulders with the sublime domes of the St. Nicholas Naval Cathedral. Just south along the coast, Liepāja is a charming Latvian port city where maritime history meets with quirky modern culture. You’ll have a chance to wander on your own before we settle down for dinner and an overnight stay in Liepāja.

Once upon a time, Karosta Prison was one of the most notorious high-security prisons in the Baltics. Nowadays it offers an immersive museum experience, and we’ll pay it a visit this morning. If you prefer, you can also explore Liepāja some more and we’ll pick you up later. Later today, entering Lithuania, our first stop is the Plokštinė Missile Base, a Cold War nuclear missile silo complex that’s now a museum. Finally, we’ll explore the famous Hill of Crosses, a deeply moving site of Catholic pilgrimage where more than 100,000 individual crosses form an extraordinary shrine to those who died in the struggle for self-determination. We’ll wind down at the end of the day at our accommodations in the small city of Šiauliai.

Today we’ll visit Kaunas, recently announced as the 2022 European Capital of Culture. Before we hit the city, we’ll stop at the Ninth Fort and its Memorial to the Victims of Nazism, a massive monument raised in memory of the many political prisoners who perished here during World War II. We’ll find our hotel in Kaunas, then relax over lunch. In the afternoon, we’ll learn from a local guide about the city’s long and complex history, its eclectic architecture, fortress, and rich Jewish heritage. After exploring Kaunas on foot for the afternoon, we’ll rest our feet and enjoy a dinner of traditional Lithuanian cuisine.

Take the morning in Kaunas at your leisure. You can explore more of the city’s many hidden gems, or sleep in and relax. We’ll meet around midday for lunch, followed by a drive south to visit Grūtas Park. Since opening in 2001, this lush, wooded park has collected the Soviet-era monuments that were torn down in the restoration of Lithuania's independence. We’ll stroll the forest tracks looking at stone mementos of Lithuania’s recent history, then stop for the night in nearby Druskininkai. Since the Tsarist era, Druskininkai has been a popular spa destination, and you’ll have the option of trying some traditional treatments this evening before dinner.

Last but not least, we’ll head northeast to Vilnius, the Lithuanian capital. Our last Baltic capital is a smorgasbord of medieval baroque and neoclassical architecture. We’ll take a tour through the city’s Old Town and learn about Užupis, a self-declared independent republic—complete with its own bill of rights—nestled in a bohemian district of Vilnius. Later we’ll go for a final dinner at a superb local restaurant, where we’ll eat, drink, and reminisce on all we’ve seen together.