Traveling to Tuscany to visit the medieval hill towns can make for the perfect trip. It combines rich history, natural beauty, medieval architecture, art and culture, great regional Italian food, and breathtaking and awe-inspiring landscapes.

Whether you take a tour, or drive, or do day trips from a major city–you will become enamored with Tuscany’s magical charm and beauty. On a recent trip with friends, we booked a rental car with built-in navigation, researched and identified the hill towns we wanted to visit for the week and for each day, and stayed in two different Air B&B. We based ourselves in two locations in Tuscany, each for a week. Our first week we stayed in the tiny medieval village of Montegabbro close to San Gimignano and Volterra, and the second week we stayed in the hill town of Montecchiello near Pienza. From there we traveled to between 3 to 5 hill towns per day, and walked anywhere from 6 to 15 miles per day depending on the number of towns we visited. Each week we took a day off for a hike or a visit to a spa town soaking in the beautiful, warm natural spring waters that make the town famous. Even seeing as many hill towns we did, big and small, there are many more to visit on the next trip!