If you’re up for a little more adventure, keep on driving to Arezzo, 25 miles from Montepulciano. You’ll find plenty more fabulous things to experience here, such as Cathedral of Saints Peter and Donato and Basilica of San Francesco. Perugia, 30 miles away, is another road-trip destination that’s worth the journey. Check out Piazza IV Novembre and Rocca Paolina, two top-notch sights in the area.