Once a year, Chișinău changes its schedule. On the first weekend of October the main square of the city turns into one long tasting: winemakers from all over the country set up tables, the people standing behind them are the winemakers themselves rather than promoters, and you can ask any of them what exactly is in your glass. This is Wine Day. I live in this city, and every autumn I watch guests arrive for the festival who, until then, knew exactly one thing about Moldova: the wine is good.
Plenty of people will tell you about the square. What interests me is the rest of your days. Because the wine you'll taste at the festival wasn't born on the square. It was born in limestone tunnels ten kilometres from the centre, in cellars in the south, in villages where plăcinte are baked while you watch. That's where I drive.
The main thing to know about the date: it moves. Wine Day is always held on the first Saturday and Sunday of October, so the exact dates shift every year. In 2026 that means 3 and 4 October. Plan it like this: arrive on Friday, give Saturday to the square in full, and after that the country begins.
The festival takes place on the Great National Assembly Square, right in front of the Government building. Entry is free, tastings are paid on the spot. It has been held since 2002, and over the years it has become an event people book flights to Chișinău for.
What to expect: winery tables, big and very small, music, food, and a crowd that gets very friendly by the evening. A local's advice: don't try to taste everything. Pick three or four producers you've never heard of and talk to the people at the table. It's the one day of the year when a winemaker from a distant village stands in the centre of the capital and is glad of every question.
Moldova is small, and for a visitor that is its great convenience. Almost everything worth seeing lies within a day of Chișinău: Cricova at 10 km, Old Orhei at 60, Tiraspol at 70, Comrat at 100. Half the main places fit into a single day of daylight; the rest deserve two.
My format is simple. In the morning I pick you up at your hotel or apartment, I drive, and I do the talking, in English, German, Russian or Romanian. Only your own party in the car, no strangers and no rigid timetable. Want to sit on a rock at Old Orhei a while longer? We sit. Tired? We head back early. Lunch in a village house is a proper part of the day, not a pause: the food is cooked in front of you, the wine comes from the vineyard across the road.
My most frequent route, and not by accident. We start at Cricova: ten minutes from the city, and the car drives straight underground. Under the limestone there are 120 kilometres of streets named after grape varieties, and part of the tour happens on wheels. Then the tasting room, usually three wines, and back up into the light. Next, Curchi monastery in a pine forest: white walls, green domes, forty minutes is enough, and the coach tours somehow drive right past it. Lunch in Butuceni, in a stone farmhouse with a wood-fired oven, run by the third generation of the same family. And to finish, Old Orhei: a 13th-century cave monastery above a bend of the Reut, still active, with monks living in it. Fifteen minutes uphill over rough stone from the car park, but between two and four in the afternoon the limestone glows. I've written a separate article about this day, and here is the route itself: Curchi, Old Orhei, Cricova.
If you only have half a day free, say Sunday morning before going back to the square, take this one. The Manuc Bey Palace in Hîncești, then Milestii Mici, the country's second underground wine city and the largest cellar in the world: a million bottles in its galleries. Six hours, and by mid-afternoon you're back in town: A palace, then the largest cellar in the world.
You'll hear about Purcari on the square for sure: it's the red that was once served at royal tables. But I'd suggest going there yourselves, because on the way stands the church in Căușeni, sunk halfway into the ground, with frescoes inside. Lunch that day is not in a restaurant but at a family's home in the village of Carahasani, at the Cobza farmstead: village cooking you won't find in the city, and I take care of that myself. Two places rarely combined in one day, and that's a shame: Frescoes below ground, a red above royal tables.
There's an option for those who want to stay close to the city. In the morning we walk the centre of Chișinău, stop at an old wooden church on the way, and by lunchtime we reach Castel MIMI in Bulboaca, a winery that looks like an estate off a postcard. By evening you're back on the square. It is, I'll admit, the laziest wine day I can offer: The capital first, the castle after.
This is where the real Moldova begins. Guests who fly in for Wine Day for a week ask me the same question every time: what else? Here it is, by direction.
Half an hour to an hour from Chișinău and you're in a territory that isn't on most maps. Bender fortress on the Dniester, a bridge beyond which the number plates change, Tiraspol with its House of Soviets and Lenin out front, the Kvint brandy distillery that has been working since 1897, and a tasting of four or five ages that usually changes the mind of anyone who "doesn't drink brandy". Passport only, the border usually takes three to five minutes, and I handle it. One day is enough to see everything that matters: A day on the other bank.
Tipova and Saharna, two monasteries above the Dniester cliffs, waterfalls, and a road you want to stop on every ten minutes: Two monasteries above the Dniester. If you'd rather keep the wine theme going, swap Saharna for a winery: The cave monastery and the winery. And the longest northern day leads to Soroca: the fortress with five towers, Gypsy Hill with its mansions, and the Candle of Gratitude above the river: North to the fortress with five towers.
Gagauzia: a hundred kilometres south and a different language outside the window. The Gagauz speak a Turkic language, live in the steppe, and feed you so well that after lunch with a family the tour continues at a noticeably slower pace. Comrat, the capital of the autonomy, Besalma, and the wine estates of the Bugeac steppe along the way: South, to a people with its own capital.
Yes, you can go to Odesa from here and be back by night: 200 kilometres, the border at Palanca, the whole day from start to finish. It's a story of its own, and I'll be honest: we check the situation on the morning of departure, and if we have any doubts we switch to a route inside Moldova at no extra cost. Details here: One day in Odesa.
If you'd like a piece of everything on this list, that works too. You tell me what interests you, wine, monasteries, the Soviet layer across the Dniester or simply the road, and I fit a day into the daylight hours and send you the price for the car before you book anything: One day in Moldova, built around you. And for those who've come for longer there is The full journey: seven to ten days, one to three hours of driving a day, nights in village guesthouses, the dawn service at Old Orhei and an evening on the Dniester. In a week like that, Wine Day turns out to be only the first evening.
I'm a licensed guide, I've been driving guests around Moldova since 2019, and I do it all year round. I drive, I tell the story, in four languages, and I switch between them without pausing if your party speaks more than one. One person answers for the day: me. On busy dates a guide from my CarPoint team may drive it instead, same route, same car, but I organise the trip and I'm responsible for how it turns out.
Pick-up anywhere in Chișinău, water in the car, child seats on request. Entry tickets to monasteries, winery tours and tastings, and lunch you pay on the spot, separately from the trip. Festival weekends in Chișinău are busy, so if you already know your dates, write early: we'll arrange the days around the square so that the mornings are underground and the evenings are at the festival.
Come for Wine Day. Then give me one day, and I'll show you where that wine comes from.
Tell me your dates in Chișinău and I'll build the days around the festival: a morning underground in Cricova, an evening on the square, and after that anywhere up to the Dniester.
In the morning we walk down to cells cut into the limestone above the Dniester and climb back up, then a village lunch with a family in Lalova and a winery in Orhei. Here is how the day works and who it suits.
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Ten hours, roughly 320 kilometres and one town on the Dniester at the end of the road. Here is how my longest day out works and who it suits.
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An hour and a half under oaks and hornbeams in the morning, then a wine tasting with lunch overlooking the vineyards. How the day works and who it suits best.
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