The capital Chişinău is by far Moldova’s largest and liveliest city and its main transport hub. While the city’s origins date back six centuries to 1420, much of Chişinău (pronounced kish-i-now) was levelled in WWII and by a tragic earthquake that struck in 1940. The city was rebuilt in Soviet style from the 1950s onwards, and both the centre and outskirts are dominated by utilitarian high-rise buildings. That said, the centre is surprisingly green and peaceful. There are two large parks, and main avenues cut through groves of old-growth trees that lend a serene element.

Of Moldova's many vineyards, Cricova is arguably the best known. Its underground wine kingdom, 15km north of Chişinău, is one of Europe's biggest. Some 60km of the 120km-long underground limestone tunnels – dating from the 15th century – are lined wall-to-wall with bottles. Legend has it that in 1966 Soviet cosmonaut Yury Gagarin entered the cellars, re-emerging two days later. Russian president Vladimir Putin even celebrated his 50th birthday here.

Similar to Cricova but bigger and possibly more impressive, the wine cellars at Mileştii Mici (20km south of Chişinău near the town of Ialoveni), stretch for 200km. The cellars here hold more than 2 million bottles, which makes this the world's largest wine collection, according to the Guinness World Records.

Occupying a remote, rocky ridge over the Răut River, the open-air Orheiul Vechi Monastery complex includes ruins, fortifications, baths, caves and monasteries, ranging from the earliest days of the Dacian tribes more than 2000 years ago through the Mongol and Tatar invasions of the early Middle Ages and the time of Ştefan cel Mare, and all the way to the modern period. he most impressive sight is arguably the Cave Monastery built inside a cliff overlooking the gently meandering river.

The northern city of Soroca occupies a prominent position on the Dniestr River and as such has played an outsized role in the defence of the Moldavian principality through the ages. The main attraction is the Soroca Fortress, part of a chain of medieval military bastions built by Moldavian princes from the 14th to the 16th centuries to defend the principality's boundaries.

TRANSDNIESTR

The self-declared republic of Transdniestr (sometimes called Transnistria), a narrow strip of land on the eastern bank of the Dniestr River, might just be one of the strangest places in Eastern Europe. It's a ministate that doesn't officially exist in anyone's eyes but its own. It maintains its functional autonomy with military and economic support from Russia and is recognized only by the three UN non-member states of South Ossetia, Abkhazia and Republic of Artsakh.

From the Moldovan perspective, Transdniestr is still officially part of its sovereign territory that was illegally grabbed in the early 1990s - with Russian support. Officials in Transdniestr see it differently and proudly point to the territory having won its 'independence' in a bloody civil war in 1992. A bitter truce has ensued ever since.

These days, a trip to Transdniestr from Moldova is relatively easy and completely safe. Visitors will be stunned by this idiosyncratic region that still fully embraces the iconography of the Soviet period (lots of photo-worthy busts of Lenin are scattered about) as well as having its own currency, police force, army and borders.

Tiraspol is the 'capital' of Transdniestr and also, officially at least, the second-largest city in Moldova. Just don't expect it to be anything like the chaotic Moldovan capital: here time seems to have stood still since the end of the Soviet Union. Eerily quiet streets, flower beds tended with military precision and old-school Soviet everything from street signs to litter-free parks named after communist grandees.