Turning your back on Monteriggioni with its towers and walls, take the gravel roads of the Montagnola Senese in the direction of the abandoned ancient village of Cerbaia. The path continues through woods and countryside, intercepting the Chiocciola and Villa Castles, whose towers pierce the history of the place. You then descend to the reclaimed plain of Pian del Lago, once marshy, drained thanks to structures such as the Grand Duke Canal, still appreciable today along your way, to continue to Via dell’Osteriaccia. A short detour is recommended here, leading to the Hermitage of San Leonardo al Lago, which can be visited by ringing the bell from 9:30 a.m. to 3:30 p.m. every day except Monday.

Finally, cross the Renai forest to Porta Camollia, the Via Francigena entrance to Siena. Arriving in the historic center is a feast for the eyes: pietra serena, medieval symbols, the majestic Piazza del Campo, the Duomo (Cathedral) and Santa Maria della Scala gather evidence of centuries of history.

This stage is short but challenging due to the scarcity of water and refreshments so refuel at La Villa Rest Point.

Nestled in the quiet woods among the Sienese hills, the Hermitage of San Leonardo al Lago stands in Santa Colomba, very close to the route of the Via Francigena, in an area once occupied by a lake that dried up in the 18ᵗʰ century. Its origins date back to before the 12ᵗʰ century. It was then entrusted to the Augustinians in 1239. Fortified in 1366 to protect the local population, it was an important place of spirituality, also frequented by Blessed Agostino Novello. The hermitage experienced a period of splendor with the extension of the Romanesque Church in Gothic style and the creation of frescoes, including a Marian cycle by Lippo Vanni and a Crucifixion attributed to Giovanni di Paolo. 

Siena emerges as a significant hub along the Via Francigena, where its historical, artistic and social richness is deeply intertwined with its hospitality and intrinsic magnificence.

A work preserved in the Biccherne Museum of the Siena State Archives illustrates the arrival of an ambuscade in 1498, with horsemen and foot soldiers entering the city from the northern stretch of the Via Francigena, between the Antiporto and the Torrazzo di Camollia. This scene, attributed to a painter close to Girolamo di Benvenuto, captures the amazement of the ambassadors upon spying the beauty and elegance of Siena. The episode is set in the context of Pandolfo Petrucci’s policies and may represent the arrival of the Venetian ambassador Alvise Sagundino. The presence of xenodochia and lodging facilities, such as the small hospital of Sant’Antonio and that of the Santo Sepolcro on that stretch of the Via Francigena underscores Siena’s importance as a stopping point for pilgrims and wayfarers. Today’s visitors can still identify with the awe of those who reached Siena in the late 15ᵗʰ century.

The city’s artistic heritage is further evidenced by the Siena Cathedral, erected in the 12ᵗʰ century right across from a Spedale (an old term in Tuscan dialect for “hospital”) that would welcome pilgrims. The Santa Maria della Scala Museum Complex represents the main hospital built on the Sienese section of the Via Francigena. Cited as early as 1090 as “xenodochium et hospitalis,” its mission was to welcome pilgrims, assist the poor and care for abandoned children. Almost all the great Sienese artists contributed to this complex, including the great pilgrim track, built in the 14ᵗʰ century and frescoed in the mid-15ᵗʰ century. The frescoes, painted by artists such as Lorenzo Vecchietta, Domenico di Bartolo and Priamo della Quercia based on an iconographic program by Rector Giovanni di Francesco Buzzichelli, celebrate the history of the hospital and its many activities of hospitality, care and assistance. Siena thus emerges as a city that not only marveled in magnificence but also embodied a deep sense of charitable work and welcoming, pillars of its identity along the ancient Via Francigena.

A symbol of Siena, Piazza del Campo is one of the most recognizable and visited medieval squares in Europe. With its unmistakable shell shape, it hosts the famous Palio twice a year, transforming this place into a vibrant theater of tradition and popular passion. This Piazza is overlooked by historic monuments such as the Palazzo Pubblico, seat of civic power, with the Loggia dei Nove and the Civic Museum housing extraordinary frescoes by Ambrogio Lorenzetti and Simone Martini. On the opposite side is the Fonte Gaia, a 19ᵗʰ-century copy of Jacopo della Quercia’s original, fed by the Bottini, the ancient underground water system. The 335-feet (102-meter) Torre del Mangia dominates the square, offering a breathtaking view of the entire city from above. Ultimately, Piazza del Campo embodies the history, art and collective soul of Siena.

Slanting skyward beside the Palazzo Pubblico, the Torre del Mangia is one of the absolute symbols of Siena and communal freedoms. Built between 1338 and 1348 in brick topped with travertine, it reaches 335 feet or 102 meters, including the lightning rod, to be the third tallest tower in Italy. It was named after the first bell ringer, nicknamed “Mangia” for his reputation as a spendthrift. The belfry, built by Agostino di Giovanni to a design by Lippo Memmi, has housed the “Campanone” (“Big Bell”), dedicated to Our Lady of the Assumption, since 1666. Those who climb its more than 300 steps are rewarded with an extraordinary view of Siena and the hills beyond. Access is from the Cortile del Podestà, next to the Civic Museum. 

Inside the Gothic Palazzo Pubblico, the Siena Civic Museum holds a treasure trove of art and local memory, telling the story and identity of the city through extraordinary artworks. The Sala del Mappamondo (World Map Room) displays masterpieces by Simone Martini, including the Maestà and Guidoriccio da Fogliano. The famous Sala dei Nove houses Ambrogio Lorenzetti’s cycle on Good and Bad Government, a powerful political allegory. The Sala di Balia houses frescoes by Spinello Aretino dedicated to Pope Alexander III, while the Anticappella displays Famous Men by Taddeo di Bartolo. In the Sala del Concistoro, Beccafumi’s Mannerist cycle of Public Virtues stands out. The tour ends in the scenic Loggia dei Nove, overlooking the Orto de’ Pecci. 

With its white, black and red marble façade, the Siena Cathedral is a breathtaking Romanesque-Gothic masterpiece. Dedicated to Saint Mary of the Assumption, it was consecrated in 1179 then enlarged in the following centuries, yet the ambitious expansion project was interrupted by the plague of 1348. The façade, also created by Giovanni Pisano, combines red, white and green marble in a refined and symbolic style. Inside, black and white—the symbolic colors of Siena—dominate. There are masterpieces such as the pulpit by Nicola Pisano, youthful statues by Michelangelo, the Piccolomini Library frescoed by Pinturicchio, along with works by Donatello, Beccafumi and Duccio di Buoninsegna. The marble floor, composed of 56 figured panels, is one of the most extraordinary works of Italian art. Also not to be missed is the “Gate of Heaven,” a scenic route between the roofs of the cathedral and the frescoed crypt which resurfaced in 1999.

Once one of the oldest hospitals in Europe, Santa Maria della Scala is now a museum complex that chronicles centuries of care, welcoming and art. Founded to welcome pilgrims along the Via Francigena, it offered treatment, hospitality and support to the frail. The tour begins in the Sala del Pellegrinaio, with 15ᵗʰ-century frescoes depicting daily life in the hospital. The tour continues through chapels, sacristies and the Corticella, the heart of the complex, where the original Fonte Gaia statues and the Treasure of Santa Maria are located. On the lower levels, the tunnels house the Archaeological Museum and the history of Siena from its origins to the Middle Ages.