This is the most complete one-day tour along the historic Via Francigena, the ancient route once traveled by medieval pilgrims, Crusaders, and Templars on their way to Rome. Your experience begins with pickup by an English-speaking private driver from your accommodation. Travel through the rolling Chianti hills, following stretches of the legendary Via Francigena. San Gimignano is the first stop, where you will enjoy a self-guided visit of the iconic medieval town known as the “Town of Fine Towers.” After exploring its historic streets and artisan shops, the tour continues through the heart of Tuscany, combining history, landscapes, wine, and local traditions along one of Europe’s most important medieval routes.

After visiting San Gimignano, the tour continues to a traditional winery farm for a relaxed lunch and tasting experience with a stunning view of the towers of San Gimignano. Enjoy a tasting of 5 Tuscan wines, including Chianti Riserva, Super Tuscan, Sangiovese, and Vernaccia di San Gimignano, paired with 5 extra virgin olive oils, 3 balsamic vinegars, and truffle specialties. Learn about wine and food pairings, Italian culinary traditions, and Tuscan winemaking in an authentic and informal setting. A traditional 3-course Tuscan lunch is included, featuring bruschetta, homemade pasta, Tuscan cured meats, and Pecorino di Pienza cheese. The full experience lasts approximately 2 hours, combining flavors, tradition, and unforgettable scenery.

After lunch at the winery, the tour continues to Monteriggioni Castle, one of the best-preserved and most iconic medieval villages in Tuscany. Built by the Republic of Siena as a strategic stronghold along the Via Francigena, Monteriggioni once controlled the main medieval routes used by pilgrims, merchants, and crusaders. Walk inside the perfectly preserved stone walls and enjoy breathtaking panoramic views over the Chianti countryside. You will have free time to explore the village, stroll along the historic walls, and visit the medieval weapons museum, gaining an authentic insight into life and warfare during the Middle Ages.

In the afternoon, after visiting Monteriggioni, the tour proceeds to Siena for a self-guided visit. Located in the heart of Tuscany, Siena is the capital of its province and a city renowned for its medieval architecture and the stunning Piazza del Campo, one of the most beautiful squares in Italy. Its historic center is a UNESCO World Heritage Site. Explore key landmarks such as the Duomo, the Baptistery, and the charming narrow streets of the historic center, including Via di Città. Siena is also famous for the Palio horse race, held twice a year, which draws visitors from around the world. Wander at your own pace and immerse yourself in the city’s rich history, culture, and atmosphere.

In the late afternoon, the tour continues to a Chianti winery farm for a second wine tasting experience before heading back. Here, you will savor Chianti Classico and Chianti Riserva, produced using traditional methods that preserve the authentic flavors of the region. Enjoy the unique character of these wines in a beautiful setting in the Chianti countryside. After the tasting, the tour concludes with a return to your hotel, B&B, or private accommodation, wrapping up an unforgettable day in the heart of Tuscany.