Driving in any Italian city is usually madness. But doing so outside of the metropolis is a pleasure given the courteous drivers, impeccably maintained roads, and clear, frequent signage. Even the rural roads that wind through the countryside are smooth and marked often with mileage and directions to nearby destinations.
One of the best road trips in Italy starts southeast of the city of Siena, following route N416 along some of the most scenic vistas in the country. The road is full of swooning landscapes and verdant fields bordered by Cypress trees, not to mention ancient monasteries and farmhouses that dot the road. Also along the N416, a road that runs east-west through the valley, are three Tuscan hill towns most worthy of a visit on this most heavenly road trip. It's easy to hit all three in one day, but for the more leisurely vacationer, you can easily spend a full day in each.
Montepulciano is walled-in and perched along a ridge high above eastern Tuscany. It's reached after a long and winding drive, through various resorts and rustic hamlets, up and over and down and around the grape-lined hillsides. Within the walls is a charming Renaissance town replete with piazzas and churches, narrow streets and more wine shops than you could visit in a year. The prize offering is the town's namesake: Vino Nobile di Montepulciano, a hearty and sophisticated red. Walk the circumference of the city, get back in your car and take the cypress-lined road that leads dead west towards Pienza.
The lofted, tiny village of Pienza, a UNESCO World Heritage Site, has one main corridor of enotecas (wine bars), churches, gifts shops, and purveyors of the local specialty: Pecorino cheese. This is not the salty, grated step-sibling of Parmesan, but fresh sheep's cheese that is soft and sweet, still packing a punch. Along the backside of town is a generous walkway that opens to the Val d'Orcia in dazzling splendor.
The steep drive up into Montalcino is spectacular and a little scary. Driving towards the sky provides a real sense of the elevation, the slant of the hills and the abundance of light which helps this area create such special grapes. Brunello di Montalcino is the granddaddy of Italian wines. It's straight Sangiovese from these remarkable hills and climate, aged four years in oak barrels. It's a hard wine to find and even harder to enjoy at the perfect time. Within the walled-in confines of the town, premium vintages can be had by the glass, including at the old fortress converted into an enoteca or any of the remarkable trattorias tucked along the serpentine streets.