Mileștii Mici wine cellars. The Guinness-record holder for the world's largest wine collection — around 1.5 million bottles stored in 55 km of underground tunnels carved into limestone. Tours run in electric vehicles (or, if you book in advance, in your own car) past "streets" named after grape varieties. The tasting at the end is generous. About 18 km south of Chisinau.
Orheiul Vechi. A limestone promontory looping around a bend of the Raut river, with cave churches and medieval fortifications carved into the rock. The views over the valley are extraordinary, and the resident Orthodox monk will let you inside if he is there. This is the one site in Moldova that genuinely stops people in their tracks. Take a marshrutka from Chisinau (about an hour) or hire a car.
Cricova winery. Another underground city of wine, this one more polished and tourist-oriented than Mileștii Mici. The cellars extend for over 120 km and include tasting rooms, a cinema, and a vast private collection that belonged to Hermann Goering and was seized after the war. Just north of Chisinau.
Tiraspol and Transnistria. Crossing into this unrecognized breakaway republic is an experience like stepping into a parallel present. Lenin statues line the main boulevard, Cyrillic script is everywhere, soldiers guard the parliament building, and the money (Transnistrian roubles, worthless outside) features Che Guevara. It is theatrical and also real. Day trips from Chisinau are easy and the crossing is not difficult for most Western travelers.
Soroca fortress. A beautifully preserved circular Genoese-era fortress on the Dniester, in a town that also happens to have a remarkable Roma hilltop quarter known as "Gypsy Hill" — an improbable cluster of palatial houses with turrets, columns, and gold-painted facades. The contrast is striking.
Chisinau's parks and food scene. The capital is often dismissed as a transit point, but it rewards a day or two. The central park, the Stefan cel Mare boulevard, the covered market, and a growing number of good restaurants and wine bars make it more pleasant than its reputation suggests.