The rows and rows of sunflowers and grapevines, punctuated by ochre-colored farmhouses and ruins, make a tour through this large Italian region one of life’s thrills. The ancient villages rising from the landscape remind you that this sleepy Italian region is also a cradle for art, architecture, and of course, food and wine. If you are able to stroll the medieval stone roads and sunny town squares and not feel like you’ve stepped into a time machine, have another glass of Chianti, and try again.
We’ve compiled a list of five of the most pristine and picturesque hill towns to visit, whether it is your first or fiftieth trip to Tuscany. All of them can be seen on day trips from Florence or Siena, but each is also worthy of an overnight stay. Keep in mind that they do require that you have your own transportation; whether that is a car, motorcycle, or bicycle, is up to you.
San Gimignano is one of Tuscany’s more famous villages, nicknamed the “Manhattan of the Middle Ages” for its impressively tall towers, fifteen of which survive. The town dates to at least 929 A.D., and looks about the same except for the souvenir shops and gelaterias everywhere. If you’re planning on buying some typical, colorful Tuscan pottery, this is the town for it. Make sure to walk through Piazza Duomo and Piazza della Cisterna, and don’t dare leave without a lunch of mixed meats and cheeses and a giant cone of gelato. Work off the calories by climbing the winding stairs to the top of the Bell Tower, taking in the bird’s eye view of the town, and 360 degrees of Tuscan countryside.
Close to San Gimignano (both can be visited in the same day), Monteriggioni doesn’t look like a town from the outside. All you can see from the road is a thick stone wall with one arched, gated entrance, making it look more like a castle or fortress. But if you park the car and pass through the gate, you’ll find a perfectly preserved and enclosed medieval village on the other side. During the endless conflicts between Florence and Siena in the Middle Ages, the Sienese built Monteriggioni as a defensive fortification. But the walls that once kept enemies out now welcome visitors in, and the little alleys and squares inside are so cute you’ll have to force yourself to stop taking pictures for a moment, and soak in the atmosphere.
If the name Montalcino sounds familiar, it might because of its namesake Brunello wine. In 1980, Brunello di Montalcino was awarded Italy’s first Denominazione di Origine Controllata e Garantita (DOCG) distinction, and today is one of the country’s most justifiably famous wines. Both in the town and in countless farms and wineries in the area, you can taste and buy it by the glass or bottle. If you can resist taking some home, you’ve got a lot more willpower than we do. In case you need another reason to visit, Montalcino itself is small and lovely, with sweeping vistas of the countryside, and featuring a 14th-century pentagonal fortress. Want one more reason? The nearby Abbey of Sant’Antimo is a thousand-year-old Benedictine monastery still in use today by a small group of monks, whom you might bump into during your visit.
The food and wine in Montepulciano are so exquisite that you might forget to enjoy the views and Renaissance architecture as well. Archeological discoveries indicate that the town existed three or four centuries before Christ, and presumably its honey, cheese, liver pâté and pork productions haven’t changed much since then. This is the place to get gifts for the gourmets back home. And don’t forget the wine, as Montepulciano’s Vino Nobile is widely recognized as one of Italy’s most delicious, and oldest, varietals. You can stop into just about any shop and sample the goods before purchasing a few bottles to take with you.
Between Montalcino and Montepulciano sits Pienza, a UNESCO World Heritage Site, used as the set for the films Romeo and Juliet and The English Patient. Important for art historians and architects, Pienza is a pristine representation of typical Renaissance architecture and egomania: Pope Pius’s plan to turn his birthplace into a perfectly planned city was begun but never finished. What remains is an oversized town square with a photo-op wishing well, flanked by the town’s cathedral and city hall. Behind the square, Pienza’s altitude and position on the side of a hill give it a natural balcony from which to take in the panorama of the serene Val d’Orcia below.