Montepulciano 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 (see photo, below), it also does well in the Atmosphere, Art & Architecture categories. And so far, it's still somewhat off the beaten track.
My recommendations when visiting this fabulous town:
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.
Wine
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.
Food
Near the top, find a restaurant with a patio that overlooks the countryside, sit outside and enjoy the fabulous views.
Order pici pasta (if you don't know what this is, here's a photo), local pecorino cheese, and if you haven't already, try the local wild boar or cinghiale. 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.
Art & Architecture
Near the top, keep your eye upwards to spot the mechanical Pulcinella: you'll find him atop a small clock tower, 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.
Festivals
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 (convinced yet?).
However: 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. Check out the video of the race on YouTube.
The town also hosts Il Bruscello, a mid-August festival during which actors recreate scenes from the town's vibrant history.
Getting There
If you don't go in August, I highly recommend approaching Montepulciano on a bike. Make the marble church of San Biagio part of your approach and a stop on your itinerary.
By public transport: take a train to Chiusi, which is 12 km east of Montepulciano, then take a bus from there.
Photo of Tuscan countryside by Sanjay
Photo of Pulcinella by Sanjay
Photo of Montepulciano with San Biagio from www.istockphoto.com
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