Begin in front of Chisinau’s main railway station, one of the city’s most recognisable gateways. Meet your local guide, receive your first serving of Moldovan wine, and learn how the station and its surrounding district developed during the Soviet period.

Continue towards the Palace of Railway Workers, an imposing cultural building once connected to the professional and social lives of railway employees and their families. From there, pass through the Alley of Bikers, where historical architecture and contemporary urban culture come together.

As you walk, enjoy additional servings of local wine at selected stops. The wine complements the relaxed atmosphere of the experience and creates opportunities to pause, talk, and hear stories about Chisinau beyond the usual historical facts.

Continue past Hotel Chisinau and the abandoned Hotel National. Once symbols of modern hospitality and urban prestige, these buildings now tell very different stories about Chisinau’s development before and after the collapse of the Soviet Union.

See the Liberation Monument and discuss how the events of the Second World War were represented in Soviet Moldova, as well as how historical memory continues to be interpreted today. Continue towards Hotel Cosmos, one of Chisinau’s most recognisable examples of late-Soviet architecture, and stop near the monument to Grigory Kotovsky, a controversial historical figure whose presence reflects the complexity of Moldova’s twentieth-century history.

Throughout the walking tour, your guide will serve Moldovan wine while sharing historical context, local perspectives, and stories about everyday life during the Soviet period. The experience does not glorify the Soviet system. Instead, it uses buildings, monuments, and public spaces to examine how this period shaped Chisinau and how its legacy remains visible today.

The second part of the experience takes place at Chisinau’s “Soviet Flea Market.” Continue enjoying the wine while browsing stalls filled with Soviet-era objects and other vintage items. Depending on the day, you may find medals, badges, coins, watches, cameras, vinyl records, books, postcards, household objects, and unexpected curiosities.

Your guide will explain the original uses and historical context of selected objects, help you communicate with local vendors, and offer practical advice on bargaining respectfully. You will also learn how to recognise some differences between genuinely older objects and modern reproductions. Purchases are optional and are not included in the activity price.

The experience concludes at the flea market with a final serving of wine and an informal conversation about what you have seen. Leave with a better understanding of Chisinau’s complicated twentieth-century history, its contemporary local culture, and, perhaps, a distinctive souvenir with its own storey.