Map: Hill Towns of Central Italy
Map: Hill Towns: Public Transportation
Map: Driving in Tuscany: Distance & Time
The sun-soaked hill towns of central Italy offer what to many is the quintessential Italian experience: sun-dried tomatoes, homemade pasta, wispy cypress-lined driveways following desolate ridges to fortified 16th-century farmhouses, atmospheric enoteche serving famously tasty wines, and dusty old-timers warming the same bench day after day while soccer balls buzz around them like innocuous flies.
Hill towns are best enjoyed by adapting to the pace of the countryside. So, slow...down...and savor the delights that this region offers. Spend the night if you can, as many hill towns are mobbed by day-trippers.
How in Dante’s name does a traveler choose from Italy’s hundreds of hill towns? I’ve listed some of my favorites in the next five chapters. The one(s) you visit will depend on your interests, time, and mode of transportation.
For me, Volterra—with its rustic vitality—is a clear winner, and its out-of-the-way location keeps it from being trampled by tourist crowds. Multitowered San Gimignano is a classic, but because it’s such an easy hill town to visit (about 1.5 hours by bus from Florence), peak-season crowds can overwhelm its charms.
Wine aficionados head for Montalcino and Montepulciano (my favorite of the two towns)—each a happy gauntlet of wine shops and art galleries. Fans of architecture and urban design appreciate Pienza’s well-planned streets and squares. All three towns are covered in the Heart of Tuscany chapter, which also includes driving routes tying together the sights, villages, agriturismi, and wineries in the countryside.
And Assisi, Siena, and Orvieto—while technically hill towns—are in a category by themselves: Bigger and with more major artistic and historic sights, they each get their own chapter. (The Orvieto chapter also includes my all-around favorite hill town, the stranded-on-a-hilltop Civita di Bagnoregio.)
While you can reach just about any place with public buses, taxis, and loads of patience, most hill towns are easier and more efficient to visit by car.
Traveling by public transportation is cheap and connects you with the locals. While trains link some of the towns, hill towns—being on hills—don’t quite fit the railroad plan. Stations are likely to be in the valley a couple of miles from the town center, usually connected efficiently by a local bus. Buses are often the only public-transportation choice to get between small hill towns. But, as with trains, they don’t always drive up into the town itself. Fortunately, bus stations are sometimes connected to the town by escalator or elevator. (For more on traveling by train and bus in Italy, see the appendix.) If you’re pinched for time, it makes sense to narrow your focus to one or two hill towns, or rent a car to see more.
Exploring the hill towns by car can be a great experience. But since a car is an expensive, worthless headache in cities like Florence and Rome, wait to pick up your car until the last sizable town you visit (or pick it up at the nearest airport to avoid big-city traffic). Then use the car for lacing together the hill towns and exploring the countryside. For more on car rentals and driving in Italy, see the appendix.
A big, detailed regional road map (buy one at a newsstand or gas station) and a semiskilled navigator are essential. Freeways (such as the toll autostrada and the non-toll superstrada) provide the fastest way to connect two points, but the smaller roads, including the super-scenic S-222, which runs through the heart of the Chianti region (connecting Florence and Siena), are more rewarding. For more joyrides, see The Heart of Tuscany chapter.
Parking throughout this region can be challenging. Some towns don’t allow visitors to park in the city center, so you’ll need to leave your car outside the walls and walk into town. Signs reading ZTL (Zona Traffico Limitato)—often above a red circle—mark areas where no driving or parking is allowed. Parking lots, indicated by big blue P signs, are usually free and plentiful outside city walls (and in some cases are linked to the town center by elevators or escalators). In some towns, you can park on the street; nearby kiosks sell “pay and display” tickets. In general, white lines indicate free parking, blue lines mean you have to pay, and yellow lines are spaces reserved for local residents. To reduce the threat of theft (no guarantees, though), choose a parking lot instead of street parking when possible. Your hotelier can also recommend safe parking options.
For a relaxing break from big-city Italy, settle down in an agriturismo—a farmhouse that rents out rooms to travelers (usually for a minimum of a week in high season). These rural B&Bs—almost by definition in the middle of nowhere—provide a good home base from which to find the magic of Italy’s hill towns. I’ve listed several good options throughout these chapters. For more information, see “Agritourismo” on here.