4-Day Moldova and Transnistria Tour with Underground Wine Cities

Chișinău rewards lowered expectations. The capital was largely destroyed in World War II and rebuilt in Soviet style, with wide boulevards, monumental public buildings, and a central park, but the result is less oppressive than the description suggests, with a warmth the guidebooks often underplay. The Cathedral of Christ's Nativity and its triumphal arch anchor the main square, while the National History Museum holds one of the better archaeological collections in the region.

In the evening, visit Mileștii Mici, the underground wine city of illuminated limestone tunnels, navigated by car, with each intersection signed with a vintage. The cellar holds over two million bottles, and the tasting includes the estate's best Fetească Neagră and Rară Neagră, indigenous varieties most wine drinkers have never encountered.

The crossing from Moldova into Transnistria is one of the most disorienting border experiences in Europe. There is a checkpoint, border guards in uniforms bearing insignia no other country recognises, a form, a fee, a registration slip surrendered on exit, and then nothing changes visibly, except that the currency in your pocket is now worthless and the state that has just admitted you does not, by international law, exist.

Tiraspol is a Soviet city largely unchanged since the late 1980s. The main boulevard runs from the Lenin monument to the House of Soviets, with tanks from the 1992 war on plinths outside parliament. The Bendery Fortress, a sixteenth-century Ottoman citadel on the Dniester, closes the day on the way back to Chișinău.

A day for the two sides of Moldova that most visitors miss entirely. The morning drive north to Orheiul Vechi (Old Orhei) passes through the Moldovan countryside: rolling vineyards and sunflower fields, white-walled villages, and beehives in every garden. The archaeological and monastic complex is set into a cliff face in a bend of the Răut River, carved through successive civilisations, and a cave monastery dug into the limestone is still occupied by a small community of monks.

In the afternoon, continue to the Cricova cellars outside Chișinău, a second underground wine city, architecturally more elaborate and home to a private cellar once maintained by Soviet leaders. The tasting here focuses on Cricova's classical-method sparkling wine, considered among the finest in Eastern Europe.

Current operational version: enjoy a free morning in Chișinău followed by an extension to Soroca, a northern Moldovan city with a medieval fortress on the Dniester and the most significant Roma community in the country. Its hilltop neighbourhood of baroque and eclectic palaces overlooking the river is one of the more unexpected architectural experiences in the region, before an onward connection to Bucharest.

When conditions permit, Day 4 is instead a full day in Odessa, the Black Sea's great cosmopolitan port, with the Potemkin Steps, the catacombs, and the nineteenth-century Old Town. Guests booking now will have the Odessa day added at no extra cost when it can be operated safely.