The “Crowned Castle”
Monteriggioni is instantly recognisable, a perfect stone crown resting on a low hill, with a complete ring of medieval walls that still encircles the village. Built by the Republic of Siena in the early 13th century as a strategic outpost against Florence, Monteriggioni remains one of Italy’s most iconic fortified hilltowns. Its nearly intact curtain wall runs for about 570 metres and is punctuated by 14 towers and two main gates, creating a skyline so memorable that Dante himself used it as an image in the Inferno, “Monteriggioni di torri si corona”.
What to see in Monteriggioni
A visit to Monteriggioni doesn’t end with the classic photo from outside the walls. Step through one of the historic entrances, Porta Franca or Porta San Giovanni, and you are immediately inside a compact medieval world of stone lanes and quiet corners. At its heart lies Piazza Roma, the village’s main square, dominated by the Church of Santa Maria Assunta, a small but historically central building that links the life of the castle to the political and religious history of the territory.
The Church of Santa Maria Assunta is not simply picturesque, it was built in 1213, in the same year as the foundation of Monteriggioni, and it witnessed key public events, among them the moment, 10 June 1235, when delegates from Siena and Poggibonsi accepted peace conditions with the Florentines within its walls. Overlooking the square, its sober Romanesque-Gothic character fits the village perfectly, offering an interior that feels more like a living fragment of the Middle Ages than a museum piece.
One of Monteriggioni’s great experiences is the walk along the walls. Two walkways open to visitors allow you to see the village from above and, just as importantly, to understand why this fortress mattered. The panorama sweeps from the Chianti hills to the woods of the Montagnola Senese, and on clear days you can even make out the distant towers of San Gimignano. It is an easy, powerful way to turn beautiful scenery into a tangible sense of medieval surveillance, defence, and territory.
To go beyond atmosphere and views, visit the “Monteriggioni in Arms” Museum, located in the castle area, entry at Piazza Dante Alighieri 23. The exhibition is designed as a clear historical route through four rooms and several centuries, focusing on the period in which Monteriggioni served as a military outpost of Siena. You’ll find high-quality reproductions of weapons and armour from the Middle Ages and Renaissance, with explanations that make the techniques of siege and defence immediately understandable, even for visitors who are not history specialists.
If you want the village at its most vivid, plan around its medieval festival, “Monteriggioni di torri si corona”, when the castle comes alive with shows, combat demonstrations, costumed re-enactments, ancient crafts, and themed taverns that extend the visit well into the evening.
Nearby - Abbadia a Isola
Monteriggioni is deeply tied to the Via Francigena, and it makes an excellent base for short, meaningful excursions rather than long drives. A fitting nearby stop is Abbadia a Isola, a small medieval hamlet and former Benedictine monastery founded in 1001, historically positioned to control and serve travellers along the Francigena. Today, it remains one of the most evocative quiet places in the area, stone, fields, and a sense of time slowing down. There is also a beautiful walking stretch that links Abbadia a Isola to Monteriggioni along the Francigena, offering open countryside views of the castle as you approach it on foot.
