Montepulciano, Tuscany is one of my favorite towns in Italy, probably because there’s a little of everything, with a heavy focus on wine. Built on a hill and surrounded by picture-perfect countryside, it also does well in the Atmosphere, Art & Architecture categories. And so far, it’s still somewhat off the beaten track.
Wear your walking shoes, and take your time getting to the top. Montepulciano is car-free, built on a hill, and the road is a little long. But the climb is worth it.
Near the top, keep your eye upwards to spot the mechanical Pulcinella – remember Punch and Judy? He’s Punch — you’ll find him atop a small clock tower (photo below), though you may hear him first as he rings his bell to sound the hour.
Find Piazza Grande with its beautiful architecture, and climb the tower of the Palazzo Comunale for more views of the countryside, even out to Lake Trasimeno. Visit the Duomo or cathedral to admire Taddeo di Bartolo’s triptych masterpiece.
On the way up, keep your eye out for wine shops built into the hill so that you can tour one of the authentic-feeling dark and earthy cellars. Sample some of the famous Vino Nobile di Montepulciano, made from the sangiovese grape, or the equally delicious Montepulciano red, made with the Montepulciano d’Abruzzo grape. If you’re planning abundant sampling or if you’ve just finished breakfast, consider hitting these shops on the way down instead. If you want a fabulous wine tasting, put yourself in the capable hands of De’ Ricci.
Near the top, find a restaurant with a patio that overlooks the countryside, sit outside and enjoy the fabulous views. Order pici pasta, local pecorino cheese, and if you haven’t already, try the local wild boar or cinghiale. [Note: It’s easy to know which fruits and vegetables to eat when you’re in Italy: as you’re walking by the fruttivendolo shops, note which ones are plentiful. Those are the ones in season and worth ordering. The cachi, or persimmons are delicious in Tuscany when in season, though eating one may require some instruction from a local.]
Montepulciano is actually one of the few places in Italy that I recommend visiting in mid- or late August. [Usually, I steer clear of Italy in August: the entire country goes on vacation and consequently the big cities are either chock-a-block with tourists (Rome), or semi-deserted (Milan); shops and restaurants can be closed; the beaches are crowded; hotels everywhere are full, everything costs more, and the heat can be oppressive.] But, go to Montepulciano at the end of August for the Bravio delle Botti, a week-long celebration that culminates in a 10-minute race between teams formed from the town’s many Contrade. The teams are made up of two “pushers” who jog while rolling a wine barrel, mostly uphill, through the town.
There is no train station in Montepulciano so I recommend you either rent your own car or book a tour that includes a visit to the town. If you don’t go in August and you enjoy cycling, consider approaching Montepulciano on a bike. Make the marble church of San Biagio (photo above) part of your approach, eliciting a guaranteed wow! from your co-travellers. And if you do have a car, don’t miss the gorgeous nearby town of Pienza, and have an amazing lunch in the town of Montichiello, also known as the balcony of Tuscany.
But you can still get there by public transport: take a train to Chiusi, which is 12 km east of Montepulciano, then take a bus from there.
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