“As with circling round Of turrets, Monteriggioni crowns his walls; E’en thus the shore, encompassing the abyss, Was turreted with giants, half their length Uprearing, horrible, whom Jove from heaven Yet threatens, when his muttering thunder rolls.”
Dante Alighieri, Inferno canto XXXI
Castello Monteriggioni is a small walled town from the 13th century, located in the province of Siena in the Italian region of Tuscany. This town is both architecturally and culturally significant, featuring several piazzas and being mentioned in Dante’s Divine Comedy. Surrounded by the stunning Tuscan countryside, Monteriggioni stands out like a needle in a haystack, as the rolling hills, adorned with olive groves and vineyards, seem to stretch endlessly around this hidden gem.
When you view the town from a distance for the first time, it is pretty astonishing. It is one of the most recognizable walled villages in all of Italy. Inside, there is almost no traffic, making Monteriggioni an excellent place for families with children to play and wander.
Castello Monteriggioni is a charming and tranquil gem that embodies old-world appeal, an experience not to be missed. Life there is simple, offering a level of peace that few places can match. One of the most remarkable features is that the buildings within the walls of Monteriggioni are largely original and well-preserved. So, pull in, stretch your legs, and grab your camera; you’re about to be enchanted.
A Bit of History
Monteriggioni is situated on a natural hillock and was constructed by the Sienese between 1214 and 1219. It was part of the front line in their wars against Florence, as they assumed command of the Via Cassia, which ran through the Val d’Elsa and Val Staggia to the west. The town wouldn’t seem like much of a threat, but considering its location, the towering wall surrounding it, and the addition of other regional defenses, it should be clear why it still stands to this day.
The city was strategically placed as a defensive fortification in the Middle Ages due to conflicts between Siena and Florence. It is hard to believe this postcard town withstood many attacks from both the Florentines and the forces of the Bishop of Volterra. Later, in 1554, the Sienese were able to place control of the town’s garrison on Giovannino Zeti, who had been exiled from Florence. In the same year, Zeti handed the town’s keys over to the Medicean forces in an act of reconciliation with the Medicis. This was considered a “great betrayal” by the town’s people.
The Outside Wall
Castello Monteriggioni still preserves most of its thirteenth-century structures and is a unique place in the medieval Tuscan village landscape. The Monteriggioni walls were under construction between 1213 and 1219. The walls, spanning approximately 570 meters (1,870 feet) in length and standing 10 meters (30 feet) tall, encircle the town and follow the natural contours of the hill. To defend the walls, 14 towers stand on square bases set at equidistance. There are two small portals/gates at either end of the town. The main street within the walls connects the two gates, allowing for easy travel in and out of the town.
The Porta’s
The primary access to the village, the Porta Romana, faces Rome to the south and opens at the base of a tower with a large, pointed arch. It may have had a drawbridge, which had to lower itself into an external moat. To the left of the arch is an inscription commemorating the foundation of Castello Monteriggioni in the second decade of the thirteenth century. On the right is a plaque commemorating the birth of the newborn Italian unitary state in 1860.
The Porta Fiorentina opens toward Florence to the north. It is situated next to a tower and features a simple semicircular arch. Some battlements are incorporated into the masonry. There are indications that the defensive wall was initially to be lower. Similar battlements are also in the elevation of the walls on the east side. To the right of the entrance, a plaque shows the Dante verses to which Castello Monteriggioni is referred.
The Main Square of Castello Monteriggioni
The Piazza Roma is the main town square and is dominated by the Romanesque Parish Church of Santa Maria Assunta in Monteriggioni (Church of Saint Mary). This building best preserves the village’s medieval character. It was built between 1213 and the year of the foundation of Castello Monteriggioni. On June 10, 1235, within the church, the delegates of the municipalities of Siena and Poggibonsi accepted the conditions of peace with the Florentines. It became a parish church at the end of the thirteenth century. It was used for religious and civil services until the early fourteenth century.
The church has a single rectangular room. The façade is simple, featuring a beautiful portal with a stone arch surmounted by a circular opening. The interior was renovated in modern times and has plastered walls and vaulted ceilings. The church houses a bell from 1299 and a seventeenth-century painting of the Madonna del Rosario.
The Houses of Castello Monteriggioni
Local nobles, gentry, and wealthy merchants once owned several houses in Castello Monteriggioni. Some face into the piazza, and some are in the Renaissance style. The other houses and small businesses of the town face them.
Off the main piazza, smaller streets give way to the public garden. These gardens provided vital food supplies during battles and sieges when enemies attacked or surrounded the walls. Its military function ceased in the mid-sixteenth century, when the entire Sienese State, of which the village was part, was annexed to the Florentine one.
What to Do and See
A few steps into the gates, you’re already in the heart of the village, the Piazza Roma. Although it is a small town, you will immediately notice that it is full of charm and character.
The Church of Santa Maria Assunta overlooks the large square. Though small, it is impressive and one of the best-preserved traces of the town’s medieval origins. The interior is simple yet moving. The effigy of Christ, when the sun shines on it, is powerful.
The Monteriggioni in the Arme Museum features medieval and Renaissance weapons and armor reproductions. There are illustrations of accurate models of siege weapons. Each room is dedicated to a specific moment in Monteriggioni’s history, within which the pieces on display are contextualized. You can also handle and wear some weapons and armor in particular museum areas. The informational panels offer visitors a concise yet comprehensive immersion in history. The museum has placards in both Italian and English. There is a fee to enter, which includes entry to the outer walls.
Check out the Two Portes: the Porta Franca (also known as Porta Romea), which faces Rome, and the Porta San Giovanni (also known as the Florentine Gate), which faces Florence.
A tower is also available for a small fee to visit. It is a tight space and has limited visibility. In hindsight, we would have skipped it.
Though not right in town, there is a two-and-a-half-mile Castle Loop to hike. It takes about 90 minutes, and the views are gorgeous. You can start and finish in Monteriggioni.
The Fortified Walls
The outer walls of the fortified city are accessible to visitors. Today, you can walk on modern metal and glass walkways with two different balconies at the top of the wall circuit. Initially, these would have been wood. The elevation offers breathtaking views of the town and the countryside’s rolling hills, extending towards Chianti and Valdelsa. If you take a moment, it is possible to imagine soldiers guarding here long ago.
There are two sections of the wall you can climb. If you only want to climb one, choose the southern section (near the central town entrance at Porta Franca). It’s larger and has the most scenic views of the two. The ticket price is included in the Monteriggioni admission at the Arme museum entrance.
Shopping
Wander the charming cobblestone streets of Castello Monteriggioni. The shopkeepers and residents decorate the narrow passageways with flowers, greenery, benches, and personal items. There is always laundry out drying, bringing color to the setting. It provides a glimpse of everyday life in this small village.
There are several charming shops featuring local products, including wine, olive oil, honey, jam, jewelry, artisanal crafts, and tourist souvenirs. You will also find a ceramics and leather shop.
Vineyards and olive trees surround Monteriggioni. As you might expect, there are a couple of wine shops in the village where you can taste some of the local wine, Chianti. These full-bodied and intense wines perfectly match the local products grown in the area, such as saffron, cheese, honey, and grappa. Grab a bottle of Colli Senesi Monteriggioni to bring home or enjoy along your travels.
Annual Festival
Every July, a special event leads to a grand celebration. The Medieval Festival of Monteriggioni is one of the most respected medieval festivals in the region.
The city dates back to the Middle Ages; the streets are filled with artisans and cavaliers. People dress up in period costumes, creating an authentic and enchanting atmosphere. Live performances, dancing, music, theatre, children’s entertainment, duels, acrobatics, and storytelling effectively recreate what life in a village was like in the past.
The festival offers guests a chance to savor the ancient food and drink of the time. The restaurants and bars are open all night to enjoy the fare from the Middle Ages.
For more information, click the link. Monteriggioni Festival
*Fun fact: The famous video games “Assassin’s Creed II” and “Assassin’s Creed: Brotherhood” are set in Monteriggioni.*
How to Get to Castello Monteriggioni, Italy
Monteriggioni is 9 miles from the stunning city of Siena and 34 miles from Florence.
You can get there by car, which is the ideal way to visit. You will find a free parking lot at the bottom of the hill. Do the short climb to the village through the Franca or Romea Gate. To avoid the walk, continue toward the town to find a pay parking lot.
The nearest train station is at Castellina Scalo, a couple of miles from Monteriggioni on the Empoli-Siena train line.
Planning a trip to Italy? Check out our Italy Travel Guide
Where to Stay
This may be a tiny town with a population of about 50 residents. Though we did not stay overnight, it would undoubtedly be beautiful and peaceful once the day tourists all left.
Most people who visit the area pass through on a day trip from Florence. If you can stay in the area, Siena is another excellent option, located nearby. We have provided links to accommodations in both cities below. Expedia and Booking.com are provided for price comparisons.
It is essential to compare prices for accommodations across various websites. Expedia is a US-based company, whereas Booking.com is a European-based company. Not all properties appear on both, so it is ideal to check both out. Our personal first choice is Booking.com. If the establishment has a website, check the price there as well. Click the link below to check out hotels and vacation homes in the area. It may be just the motivation you need to start planning that next grand adventure.
Where to Eat in Castello Monteriggioni
This is a small town, but there are some lovely restaurants where you can enjoy local fare paired with some of the region’s Chianti wine. The top-rated restaurants include Ristorante le Torri Monteriggioni, Antico Travaglio—Osteria Gelateria, and Casalta Ristorante.
When to Visit
There is no wrong time of year to visit Monteriggioni. The walls, Monteriggioni in Arme museum, restaurants, and cafes are open year-round. The peak season is from May to September. The busiest time is during the Medieval Festival in July. It can get busy, but it is quite the event!
| Average Temps | |
| January | 40°F (4°C) |
| February | 41°F (5°C) |
| March | 47°F (8°C) |
| April | 53°F (11.5°C) |
| May | 61°F (16°C) |
| June | 69°F (20.5°C) |
| July | 74°F (23°C) |
| August | 73°F (22.5°C) |
| September | 66°F (19°C) |
| October | 58°F (14°C) |
| November | 48°F (9°C) |
| December | 41°F (5°C) |
While in the area…
Like much of Italy, Monteriggioni boasts many lovely churches, including the historic Santa Maria Castello Parish Church. There are many impressive homes and small villages in the Tuscany countryside, such as Abbadia Isola, a delightful ancient village that is well worth a visit.
It is expected that if you are visiting Monteriggioni, you will either be visiting Siena or coming from there. If Siena is not yet on your schedule, you must add it. It is one of the most striking and fascinating of the walled cities of Tuscany. The Siena that welcomes you today is essentially the same as it would have appeared back in 1300. Preserving its unique medieval architecture draws so many to this magnificent city.
Final Thoughts
When looking for more well-known towns like Siena, Monteriggioni can easily be missed. It’s a perfect quick stop when traveling the region between the larger city of Florence and the more famous hill towns scattered throughout Tuscany. You can slow down, take in the beautiful scenery, sip local wines, and let the old-world charm wash over you. There are not many places like this, and it would be a shame to miss out on something so genuine that is on your path. We have no doubt you will be as captivated as we were.
© 2025 Wanderers Compass All Rights Reserved
Check out the Official Tourism site for Monteriggioni, Italy
Our Castello Monteriggioni Italy Photo Gallery
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