Not to miss

Chisinau

Chisinau is a surprisingly green city on the banks of the Bac (Byk) River. It's the transport hub of the country, but its tree-lined streets resemble a provincial town in Romania rather than a capital city. Though severely damaged during WWII, a wealth of stately buildings and cathedrals survive.

Mixed in with these are the stark, grey boxy buildings from the Stalinist era, offset by a number of bars and cafes sprouting up around the city and trying hard to swim against the prevailing economic current. Once in the surrounding rural areas, however, the extent of the poverty becomes obvious.

With the exception of the statues of the famous writers Alexander Pushkin (who spent his exiled years in Chisinau) and Mihai Eminescu, nearly every other piece of upright masonry in the city is a war monument of some sort. Inside the Stefan cel Mare Park, which dominates the western flank of Blvd Stefan cel Mare, is the statue of Stefan cel Mare. Needless to say, the medieval warrior-prince is still something of a hero in Moldova.

Transdniestr

Transdniestr has been a thorn in the side of the Moldovan government since the predominately Russian republic was first formed in 1991. It is a self-declared republic with Tiraspol as its capital city and its own currency, army, media and police force.

Transdniestr really started looking like it had slipped down a rabbit hole when it began drawing imaginary borders and protecting them with (unofficial) border guards holding (real) guns.

Rampant inflation, a shaky currency, low wages, and soaring debts have put Transdniestr behind the economic eight ball. Nevertheless it's worth a visit. It's a walking, talking, breathing mausoleum of Stalinist-style government. There are no golden arches, Coca-Cola signs or cafes selling double decaf-cafs here. It's all peasant pragmatism and Stalinist utilitarianism. And they don't go much for US travellers either.

Orheiul Vechi

Orheiul Vechi ('Old Orhei', marked on maps as the village of Trebujeni) is arguably Moldova's most fantastic sight. It's certainly among its most haunting places. The Orheiul Vechi Monastery Complex, carved into a massive limestone cliff in this wild, rocky, remote spot, draws visitors from around the globe.

The Cave Monastery (Mănăstire în Peşteră), inside a cliff overlooking the gently meandering Răut River, was dug by Orthodox monks in the 13th century. It remained inhabited until the 18th century, and in 1996 a handful of monks returned to this secluded place of worship and are slowly restoring it. You can enter the cave via an entrance on the cliff's plateau.

Cricova

Cricova is the Grand Duke of Moldovan wineries. Its underground wine kingdom is one of Europe's biggest, with 120km (74mi) of labyrinthine roadways, 60 of which are used for wine storage. Up to 100m (328ft) under ground, the 'cellars' hold 1.25 million bottles of rare wine. You must be in private transport and have advance reservations to get into Cricova.

Capriana Monastery

You may be a little tired and emotional after your visit to the vineyards and ready for something restful and spiritual. There's an old monastery conveniently located 7km (4.5mi) southwest of Straseni in the isolated village of Capriana where you can repent of your drinking ways and give your liver a rest. It's a 14th-century monastery that miraculously survived the militant atheism of the Soviet era and its obligatory looting and pillaging. Sitting serenely at the edge of a lake, it's comprised of three sections, each built in a different era. The oldest is the church of the Virgin's Assumption, built in classic 14th-century baroque style. Saint Nicholas' Church was built in the 1800s and Saint George's church (abutting the abbot's house, refectory and cells) was built at the turn of the 20th century. Forty-two Orthodox monks still use the monastery today.

Three buses leave daily from Chisinau to Capriani, but they begin their 30km (19mi) trip back to Chisinau almost immediately. This makes a day trip difficult.