Walk Italy's Via Francigena: San Miniato, San Gimignano & Siena - 5 Days

Day 1: Arrive in the Tuscan Hill Town of San Miniato

Welcome to Italy! After you arrive by train in San Miniato—which is located halfway between Florence and Pisa—a taxi will take you to the city center. Here, you can explore a typical Tuscan hill town, learn about its history since the Middle Ages, and discover its importance to the Via Francigena.

This historic pilgrimage route once ran from Canterbury to Rome and was first traveled by the Archbishop of Canterbury in 990 CE on his well-documented journey to see the Pope. Today it provides walkers with one of the country's most scenic and varied hiking routes, passing through rolling Tuscan countryside dotted with walled medieval hill towns. Tomorrow you'll set out on a three-day walk along a portion of this historic route, so spend the rest of your evening relaxing and resting up after the day's travels.

Day 2: Walk to Castelfiorentino, Relax in a Traditional Tuscan Farmhouse

Embark on your first day of the Via Francigena pilgrim's route, traveling about three hours or 9 miles (15 km) from San Miniato to the small country town of Castelfiorentino on foot. You'll wind your way through typical Tuscan landscapes, with views of cypress trees, Chianti vineyards, and rolling fields as you get a healthy dose of fresh air. After an active day, you'll spend the night in comfort as you're welcomed into a typical Tuscan country farmhouse for dinner and a good night's sleep.

Day 3: Walk to San Gimignano via the Thermal Baths of Gambassi Terme

Continue on the Via Francigena this morning, making your way 12 miles (20 km) from Castelfiorentino to San Gimignano. Along the way, you'll pass through the hamlet of Gambassi Terme, known since ancient times for its thermal waters. Cool off with a dip to experience the healing properties and rest your tired feet, then get back on the trail toward San Gimignano.

This historic gem epitomizes the perfect Tuscan hill town, with 13th-century walls and 14 stately towers surrounding its UNESCO-listed historic center. While the town is perennially popular with day trippers, the streets quiet down in the evening, so tonight, you'll get the chance to experience its charms like a local as you settle into your accommodation and head out for an early dinner.

Day 4: Walk to Convento Vecchio via Monteriggioni, Transfer to Siena

From San Gimignano, you'll travel by car to Gracciano, 9 miles (16 km) south, to begin the last stage of your journey on the Via Francigena, heading toward Siena. During your walk, you'll cross the boroughs of Strove, Abbadia Isola, and the heights of Monteriggioni—an impressive fortified medieval hill town whose ramparts and towers give stunning views over the Tuscan countryside. Take some time to explore here before getting back on the trail. 

You'll continue your walk to Convento Vecchio, 16 miles (26 km) away, where a car will whisk you on to Siena. Spend the evening discovering this significant medieval city and provincial capital, tasting authentic regional dishes like pappardelle with wild boar ragù and gnudi (gnocchi-like dumplings with spinach and ricotta), toasting your achievements with the excellent local wines, and people-watching in the famous Piazza del Campo.

Day 5: Depart Siena

Say goodbye, or ciao, to Italy for now. Take advantage of any extra time with one last morning stroll around Siena, visiting can't-miss highlights like the magnificent Duomo di Siena, a Romanesque-Gothic cathedral known for its intricate marble floor and works by Bernini, Pisano, and Donatello. When the time comes, a driver will transfer you to the airport, where you'll catch your flight home or continue your European adventure. Safe travels!

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