Medieval Hilltop Towns of Tuscany

Many great Italian artists, including Michelangelo and Giotto, first tried their hand at capturing the lustrous light that bathes Tuscany’s little-known medieval hilltop towns. Perched high upon hillsides overlooking miles of countryside, these walled villages can make anyone feel as if they have walked back in time, with their narrow winding streets and ancient cobblestone roads. Most tourists bypass these gems of architectural splendor as they head to more commonly visited Tuscan cities such as Florence and Siena. But by bypassing these romantic havens, visitors miss out on some of the country’s best local cuisine, wine and breathtaking scenery.

Thanks to Frances Mayes’ book (and the subsequent movie) “Under the Tuscan Sun,” clients may already be familiar with the elegantly appointed village of Cortona. From any hotel window in Cortona, there is a view that spans across hundreds of miles of countryside. Stunning by day, Cortona glows in the pinks and oranges of sunset each evening as visitors make their way through town to locate dinner. Evening walks are infused with the pungent scent of local wild tartufo, the truffles of this region, which are considered to be some of the finest in the world. Visitors will find their plates liberally dusted with black truffles from October through March, and with white truffles from October to December.

Villages that have attracted less attention — and hence less foot traffic — include Montepulciano, San Gimignana, Montalcino, Pienze, Volterra and Montefioralle. Wine lovers will be delighted by the selection offered at even the smallest of village eateries. Where else in the world is the house wine as good, or even better, than the pricey items listed on the wine menu?

Home to Vino Nobile, Montepulciano’s lofty streets possess views that rival Cortona. Wine connoisseurs should also be sure to stop through Montefioralle, home to some of the best Chianti. For a once in a lifetime wine tasting experience, stay in Montalcino, where you can sample wine inside of the town’s imposing castle and fortress.

Anyone intrigued with medieval architecture should be sure to experience San Gimignano. Known as the best-preserved medieval village, it boasts 15 imposing towers of the type that used to dot every hillside. For architecture and culture older than Rome, spend a day in the walled village of Volterra. Once a thriving Etruscan city before the time of the Romans, Volterra is built upon ancient ruins. Ancient Etruscan city walls can still be seen along the outskirts of town. Just within the medieval walls sits the Museo Guarnacci, where you can walk among the surviving remnants of the colorful Etruscans.

Tuscan hilltop villages cannot be spoken of without mentioning the fresh local cheese. Especially in Pienza, home of the most frequently used cheese in Italy, you can pair your wine with the highest quality pecorino on the planet.

Foodies, romantics and wine lovers will have trouble planning another trip as indulgent as a visit to the medieval villages scattered throughout the hillsides of the Tuscany region.

The Details