I did a lot of research on restaurants in Montepulciano before going and ended up going to "Osteria Del Conte" which was fabulous. Great comfort food!
Homemade pici pasta with tomato, ravioli with mushroom sauce and lamb/pork chops with grilled veg very nice..I would recommend this place... it's nothing fancy but a great example of good Tuscan comfort food. All the locals seemed to go there.
this info from the Restaurant pages might give you a start
A search should pull up some other info too; there have been discussion in the past of wine tasting excursions in this area
Osteria Acquacheta (Osteria dell'Acquacheta
)Via del Teatro, 22, Montepulciano, Tuscany , IT
localita San Biagio,15, Montepulciano, Tuscany , IT
Le Logge del Vignola
Via dell'Erbe,6, Montepulciano, Tuscany , IT