Moldova

Pretty much all roads in Moldova lead to its wine-and-food loving capital. While the city’s origins date back six centuries to 1420, much of Chişinău was levelled in WWII and a tragic earthquake that struck in 1940. The Soviets rebuilt it into what you see today: grandiose Stalinist architecture mixed with gloriously brutal modernism from the later Soviet period and a smattering of pre-WWII edifices.

Chişinău is a city of parks where retirees play chess in the shade of old-growth trees, of street festivals, and of sidewalk cafes where you can have a beverage and watch the world go by. A dozen superb wineries are within a 90-minute drive of Chişinău, and the super-central location puts the entire country within a day trip. Throw in a hip and happening nightlife, and Chisinau ticks off all the boxes for an effective weekend break.

Cricova's underground wine kingdom, 15km north of Chişinău, is one of Europe's biggest cellars. Some 60km of the 120km-long underground limestone tunnels – dating from the 15th century – are lined wall-to-wall with bottles.

Email well in advance to book a tour package. Options include the basic 90-minute tour with tastings of four wines (490 lei); the 'professional' (650 lei with cheese and tastings of seven wines); and the 'traditional' (1500 lei with tastings of eight wines and a big lunch).

The archaeological and ecclesiastical complex at Orheiul Vechi (Old Orhei), about 50km north of Chişinău, is an important historical site and a place of stark natural beauty. Occupying a remote, rocky ridge over the Răut River, the complex is known for its Cave Monastery, but also includes ruins 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.

The self-declared republic of Transdniestr, a narrow strip of land on the eastern bank of the Dniestr River, is one of the strangest places in Eastern Europe. It's a ministate that doesn't officially exist in anyone's eyes but its own.

From the Moldovan perspective, Transdniestr (also spelled Transnistria; in Russian: Prednestrove) 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 easier than ever thanks to relaxed registration rules. Visitors will be stunned by this idiosyncratic region that still fully embraces the iconography of the Soviet period as well as having its own currency, police force, army and borders.

The northern city of Soroca occupies a prominent position on the Dniestr River and as such it 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. This fortress was founded by Ştefan cel Mare and rebuilt by his son, Petru Rareş, in 1543–45.

In addition to the town's historical role, Soroca is home to a sizable Roma community and is commonly regarded as Moldova's unofficial 'Roma capital'. The incredibly gaudy, fantastical mansions of the Roma 'kings' that line the streets up on the hill above the centre are a sight to behold.

The fantastic Tipova Cave Monastery is built into cliffs that tower some 200m above the Dniestr River's right (west) bank, in the tiny village of Tipova some 95km northeast of Chişinău. The monastery consists of three religious chambers and monastic cells linked by precarious steps built into the rock face. The oldest of the three chambers, the Elevation of the Holy Cross cave church, is thought to date from the 11th century. Dress appropriately to enter any religious areas.