One of the longest and most impressive stages of the Via Francigena, at some 18.6 miles (30 kilometers) among hills, with ups and downs and breathtaking rural landscapes. From San Gimignano, walk among Romanesque parish churches, castles, medieval villages and forests. The ancient Molino d’Aiano, to this day not pinpointed with precision, marks a historic stop by Sigeric. Pass through Colle Val d’Elsa, a charming medieval village, found about halfway through the stage, perfect for staying overnight and splitting the route. Here you will encounter the “Sentierelsa” River Park, Le Caldane and the Parish Church of Strove.

The path continues to the splendid complex of Abbadia a Isola, which once appeared as an island on a lake. Finally, among the woods, the towers of Monteriggioni can be glimpsed, standing firm in the landscape like Dante’s giants. Water and refreshments can be sourced only in the towns.

A short distance from San Gimignano, nestled among vineyards and olive groves, is the Convent of Monte Oliveto Minore, founded in 1340 and expanded in 1458. Off the tourist trail, the complex houses a 15ᵗʰ-century cloister with a fresco of the Crucifixion attributed to Benozzo Gozzoli and workshop. From here, you can choose to take a looped hike of about 3.7 miles (6 kilometers) that leads through fields, woods and paths to reach an old mill and the village of Montauto, from where there is a splendid view of San Gimignano. Along the trail, you’ll recognize wild plants of folk tradition, traces of wildlife and local geological formations. The return journey is through the vineyards thanks to which the renowned Vernaccia di San Gimignano is made. 

Nestled on the heights separating San Gimignano from Monteriggioni, Colle Val d’Elsa is a splendid medieval village. Famous for its tower houses and for being the birthplace of Arnolfo di Cambio, it is also known as the “Bohemia of Italy” for its historic crystal production. The Crystal Museum, renovated in 2023, chronicles two centuries of glassmaking and the development of lead crystal. In the historic center, museums, convents and glimpses of valleys alternate with contemporary art installations that enliven the urban variant of the Via Francigena. Among the stops: the San Francesco Church, the San Pietro Museum, Piazza Arnolfo and the Teatro del Popolo.

In Colle, the past dialogues with the present in a synergy of craftsmanship, history and contemporary vision. 

In the urban section of Colle Val d’Elsa, the Upper Val d’Elsa River Park protects the course of the Elsa River, which here “comes alive,” giving rise to a lush environment rich in biodiversity. The SentierElsa, a well-equipped trail extending some 2.5 miles or 4 kilometers from Gracciano to the Spugna Bridge and traced by the Via Francigena, allows visitors to explore the landscape among footbridges, bridges and rest stops. Along the way, encounter herons, newts, carp and wrens, encompassed by an intact ecosystem.

The route also bears witness to local history, with restored ancient gore and the Caldane, thermal pools already known in Etruscan times. Finally, Diborrato surprises with its waterfall cascading 49 feet (15 meters) and deep lake below, a favorite destination for a break among nature. 

Abbadia a Isola is a little-known and charming village suspended in time, built around a Benedictine monastery from the year 1000. An abbey was built on a small island in the Cannetto Marsh, along the Via Francigena, in a strategic position that increased its importance in the Middle Ages. Referred to by Sigeric as “Borgonuovo,” it now houses a splendid Romanesque church with a fresco depicting it as emerging from the waters. Hard hit by the Black Death, it still retains traces of its former greatness.

The route from here to Monteriggioni is easy and charming, among fields of wheat and glimpses of the Castle. The Contessa Ava Hostel, housed in the monastic premises, now welcomes pilgrims seeking simple and authentic hospitality. 

A lookout on a hill, Monteriggioni is one of Italy’s most iconic medieval villages, even mentioned by Dante in his Inferno. Founded by the Sienese between 1213 and 1219 as a defensive outpost against Florence, it retains its original structure intact with an 1870-feet or 570-meter wall and 14 towers that stand out against the landscape. The village dominates the Via Cassia, the ancient strategic artery of Valdelsa. In the center, the Piazza houses the Church of Santa Maria Assunta, a symbol of medieval faith and sobriety. The village offers an impressive museum tour, Monteriggioni in Arme, with reproductions of period weapons and armor, ideal for delving into the living history of the place.