Destinations / Italy

Castello Monteriggioni, Tuscany: A Visitor Guide

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

“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, Castello Monteriggioni, Tuscany: A Visitor Guide
Picture from Adobe Stock Images

Castello Monteriggioni is a 13th-century tiny walled town, a commune in the province of Siena in the Italian region of Tuscany. The town is architecturally and culturally significant; it hosts several piazzas and is referenced in Dante’s Divine Comedy. Surrounded by the beautiful countryside of Tuscany, it seems to be a needle in a haystack as the rolling hills covered with olive groves and vineyards appear to stretch forever around this mini treasure.

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 quaint and quiet gem with old-world charm. One not to be passed over. It is a simple life there with a peacefulness few places can match. What is even more remarkable is the buildings inside the walls of Monteriggioni are, for the most part, original and intact. Pull in, stretch your legs, and grab your camera. You are about to be charmed.

A bit of history

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

Monteriggioni is located on a natural hillock, and was built by the Sienese in 1214–1219. It was part of the front line in their wars against Florence by assuming command of the Via Cassia running through the Val d’Elsa and Val Staggia to the west. The town wouldn’t seem much of a threat, but looking at its location, the towering wall surrounding it, and adding other regional defenses should tell you why it still stands.

The city was strategically placed as a defensive fortification in the Middle Ages due to conflicts between Siena and Florence. 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, Castello Monteriggioni, Tuscany: A Visitor Guide

Castello Monteriggioni still preserves most of the thirteenth-century structures and is a unique place in the panorama of medieval Tuscan villages. Monteriggioni walls were built between 1213 and 1219. The walls, totaling a length of about 570 meters (1,870 ft) and ten meters tall, encompass 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 portas/gates at either end of the town. The main street within the walls connects the two gates for easy traveling in and out of the town.

The Porta’s

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

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 been equipped with a drawbridge, which had to lower itself on an external moat. To the left of the arch is the inscription commemorating Castello Monteriggioni’s foundation in the second decade of the thirteenth century. On the right is a plaque of the newborn Italian unitary State celebrated in 1860.

The Porta Fiorentina opens toward Florence to the north. It is located next to a tower and consists of a simple semicircular arch. Incorporated in the masonry are some battlements. 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

Castello Monteriggioni
Image from Adobe Stock Photos

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 and has 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 painting of the seventeenth century with the Madonna del Rosario.

The houses of Castello Monteriggioni

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

A few of the houses in Castello Monteriggioni were once owned by local nobles, gentry, and wealthy merchants facing into the piazza; some are in the Renaissance style. They are fronted by the other houses and small businesses of the town.

Off the main piazza, smaller streets give way to the public garden. These gardens provided vital food during battles and sieges when enemies attacked or gathered around 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. Though a small village, you will immediately note it is full of charm and character.

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

The Church of Santa Maria Assunta overlooks the large square. Though small, it is impressive. It is 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 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 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 the visitor a short but thorough 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.

Castello Monteriggioni

Check out the Two Portes; the Porta Franca (or Porta Romea), which looks toward Rome, and the Porta San Giovanni (or Florentine gate), which looks toward Florence.

A tower is available to visit as well for a small fee. 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

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

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 provides breathtaking views of the town and the countryside’s rolling hills towards Chianti and Valdelsa. If you take a moment, it is possible to imagine soldiers guarding here long ago.

There are two sections of walls you can climb. If you only want to climb one, choose the southern section (near the main town entrance at Porta Franca). It’s larger and has the most scenic views of the two. The ticket price is part of the Monteriggioni at the Arme museum entrance.


Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

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 get a glimpse of everyday life in this small village.

There are several cute shops with local products, including wine and olive oils, honey, jam, jewelry, artisan 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 to 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

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

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 goes back to the Middle Ages; the streets fill up with artisans, cavaliers. People dress up in period costumes, creating an authentic and enchanting atmosphere. Live performances, dancing, music, theatre, children’s entertainment, duels, acrobats, and storytellers succeed in recreating what life in a village was like then.

The festival offers guests a chance to savor the ancient food and drink of the time. The restaurants and bars are open all night long to partake in the fare from the middle ages.

You can find more information by clicking the link. Monteriggioni Festival

*Fun fact: The famous video games “Assassins Creed II” and “Assassins Creed Brotherhood” are set in Monteriggioni.*

How to get to Castello Monteriggioni Italy

Monteriggioni is 9 miles from stunning 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

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

This may be a tiny town; the population is about 50 residents, but there is no shortage of places to eat and accommodations to stay in if you choose. Though we did not stay overnight, there was no doubt it was beautiful and peaceful at night.

Most people who visit the area pass through on a day trip from Florence. If you can stay in the area, another great choice and close by is Siena. We have provided links to accommodations in both cities below. Both Expedia and Booking.com are provided for price comparisons.

Accomodations in Monteriggioni Italy



Accommodations for Siena



If you use these links to book something, we may earn a small commission at no additional cost to you. Thank you!

Where to eat in Castello Monteriggioni

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

This is a tiny town, but there are some lovely restaurants to enjoy local fare with some of the regional Chianti wine. The top-rated restaurants include Ristorante le Torri Monteriggioni, Antico Travaglio – Osteria Gelateria, and Casalta Ristorante.

When to Visit

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

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 crowded, but it is quite the event!

Average Temps
January40°F (4°C)
February41°F (5°C)
March47°F (8°C)
April53°F (11.5°C)
May61°F (16°C)
June69°F (20.5°C)
July74°F (23°C)
August73°F (22.5°C)
September66°F (19°C)
October58°F (14°C)
November48°F (9°C)
December41°F (5°C)

While in the area…

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide
Siena, Italy

Like much of Italy, Monteriggioni has many lovely churches, such as the historic Santa Maria Castello Parish Church. There are many impressive homes and small villages in this Tuscany countryside, such as Abbadia Isola, a delightful ancient village that is well worth a visit.

It would be expected if visiting Monteriggioni, you will be visiting Siena or coming from there. If Siena is not yet on your schedule, you must ensure you 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

Castello Monteriggioni, Castello Monteriggioni, Tuscany: A Visitor Guide

When looking for more well-known towns like Siena, Monteriggioni can easily be missed. It is a perfect quick stop when traveling the region between the bigger city of Florence and the more famous hill towns scattered throughout Tuscany. You can slow down, take beautiful pictures, 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.

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