Monteriggioni Italy: Step Back in Time at This Medieval Fortress Near Siena

Your visit to Monteriggioni Italy will make you feel like you’ve stepped back in time. Here’ you’ll find one of best preserved examples of a medieval village in all of Italy. Better yet, this Tuscan castle is just 12 miles from Siena. Read on to discover everything you need to know and what to do and see in Monteriggioni so you can plan your visit to the “crown of Tuscany.”

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CONTENTS: In this article, you will learn all about Monteriggioni so you can easily plan your visit, including:

Where is Monteriggioni?

Monteriggioni is n the beautiful rolling hills of Tuscany.

You’ll find the ancient village of Monteriggioni in the beautiful rolling hills of Tuscany in Central Italy. The castle, or “castello di Monteriggioni” rises upon the relief of Montemaggio, between the Colle Val D’Elsa and Siena.

Barring traffic, the 35 mile (20 km) drive to Monteriggioni from Siena takes just under an hour. 

Monteriggioni is also just over an hour’s drive from Florence, making it an excellent Tuscan day trip from either location. So, if you wanted to, you could easily do a day trip to Monteriggioni from Florence.

This fantastic day trip is a great option since it is well priced and includes stops at some of the most popular destinations in Tuscany – Siena, Monteriggioni, San Gimignano, and the wine-growing region of Chianti.

So, throughout the course of your 9-hour day trip from Florence, you’ll visit historic Siena and admire the exquisite architecture of the Cathedral and the Palazzo Communal in Piazza del Campo.

From here, you’ll then explore the medieval walled town of Tuscany before making your way to Monteriggioni, where you can see various filming locations from the Gladiator film.

Finally, end your day with a picturesque drive through Chianti, where you’ll do a bit of olive oil and wine tasting before heading back to Florence in the evening.

Brief History of Monteriggioni

Monteriggioni Italy represents one of the best preserved examples of a medieval village in Italy. In the 13th Century, the Sienese built this walled fortress during the territorial wars against Florence. 

Ultimately, the territory was lost to Florence in 1554 and taken over with all of Seina by the Medici’s the following year.

Aside from some minor work done in the 16th century and tower reconstruction in the early twentieth century, it remains largely the same is it was in 1214.

This incredible walled village featured both Dante Alighieri’s famed three-part narrative poem, Divine Comedy (1320) and the popular cult classic video games, Assassin’s Creed II and Assassin’s Creed: Brotherhood.

Given the castle’s majesty, it’s easy to understand why Monteriggioni continues to be a modern day wonder in popular culture and tourism alike.

Important Architecture

The two massive doors equipped with shutters were once operated by a pulley system.

When you approach the Monteriggioni fortress ensconced by massive walls, it’s like something out of a fairytale. 1870 feet (570 metres) of circular walls follow the natural contours of the hill, accentuated by 14 evenly spaced towers. 

The walls are over 65-feet (20 metres) high and about 6.5-feet (2 metres) thick.

Two portals serve as the only ways in or out:

  • Franco (or Romea) Gate – facing the north toward Rome
  • Florentine Gate – facing the south toward Florence

Via 1 Maggio is the main street that connects these portals. The two massive doors equipped with shutters once operated by a pulley system. 

Piazza Roma is the main square of Monteriggioni, surrounded by villas and mansions once owned by wealthy locals, and the Monteriggioni church. A little exploration will reveal the narrow lanes and picturesque gardens of the residential area.

Rather than a moat of water, Monteriggioni was surrounded by ditches and charcoal pits protectively set on fire in an attack. 

Imagine the guards patrolling the walls, overlooking panoramic views of the surrounding lands!

The Legend of Monteriggioni

Captain Giovannino Zeti was the commander of the Montereggioni Army and also an ex-Florentine. 

He commanded the final battle between the Monteriggioni castello and the army of Florence. After the castle’s central well was severely damaged by cannon fire, their water supplies were in jeapardy. Yet he and his men vowed to fight to the death. 

Zeti fell short of his promise when it came time to meet his fate. Instead, he disguised himself and slipped out at night to negotiate with the Florentine army camped outside the walls of the fortress. 

Zeto hoped to save his life, reclaim lost property in Florence, and earn the graces of Cosimo I de’ Medici.

So, the captain betrayed his own men, breaching Monteriggioni’s security by leading some of the army into the castle to attack from the inside. After the siege of Monteriggioni, the inhabitants became slaves in Florence, and the fortress of Monterrigioni was claimed by the Medici’s, after resisting over three centuries of ferocious attacks.

Zeti was disowned and hated by the people of Siena, and tormented by his own regrets of betrayal. So much so that it’s said that Captain Ziti’s ghost roams the Monteriggioni castle walls, haunting the city in search of improbable forgiveness. 

Some believe the captain’s spirit haunts an alleged secret passage from the well of Piazza Roma leading directly to Siena. Others in Monteriggioni say they hear trotting horses and Zeti’s laments when the moon is full.

This legend of Captain Zeti is among one of the most popular ghost stories of Tuscany!

How to Get to Monteriggioni

There are a few ways you can get to Monteriggioni.

You can take the Florence-Siena dual-carriageway and take the “Monteriggioni” exit, which is about 6 mi. or 10 km from Siena. From there, follow the signs and then park in the lot at the bottom of the hill. The parking fee at the time of publication is less than 4 euro.

You can take one of the several public busses from Florence, Pisa, Siena, and Voltera, which depart daily at regular intervals.

Or, you can do as I did and take a full-day English-speaking tour by bus, which leaves from Florence and includes not only Monteriggioni, but San Gimignano, Siena, and Chianti.

In all instances, be prepared for some traffic delays. Also, it may be hard to get tickets for tourist buses during high tourist season, so book in advance.

You can also take the train but the nearest railway station (Castellina in Chianti-Monteriggio) is just under 2 miles or 3 km away from the castle.

When to Visit Monteriggioni

The high season in Italy and therefore, Monteriggioni, is June, July, August, and September. You’ll find plenty of “Tuscan Sun“-shine, summer weather, and lots of tourists. 

If you are visiting in July, you might want to take in the festival at the castle! At the Medieval Festival of Monteriggioni, (Monteriggioni Festa Medievale) you’ll find a great celebration at the fortress, which includes:

  • Re-enactments of the battle of 1269 between Siena and Florence
  • Craftsman, cavaliers, and period costume
  • Dances and live performances of music, theatre, duels, acrobats, storytellers
  • Wine and food from the Medieval Period, as well as a variety of food stalls
  • Falconry displays
  • A fireworks finale
  • The Grand Parade along the streets of Monteriggioni

Also in July is the Palio in nearby Siena. This incredible horse race that happens twice a year (July and August) and the event draws great crowds.

The low season in Italy is from late November to February, in all regions except those with winter sports such as skiing and snowboarding. 

If you’re open to cooler weather, you might opt to visit Italy during the shoulder season—that sweet spot between high and low season where the crowds are at a minimum, and hotel and air fares tend to be lower, too.

In that regard, March and April are lovely times to visit Monteriggioni and Italy as a whole. Late October and Novermber are, too.

Be aware that Easter tends to be crowded in Rome and Florence, and Carnevale, which takes place in Venice in February, is another localized high season in Italy.

Getting Around Monteriggio

Once you step through the gate of Monteriggioni, you can easily explore the fortress and its surrounding on foot in a couple of hours. It’s typically not crowded, except during the Monteriggioni festival.

Things to Do in Monteriggioni Italy

As you meander the walled-city, take your time to appreciate:

  • The medieval architecture
  • Tightly woven cobbled streets and tunnels
  • Soaring city gates
  • Ancient buildings that surround the square
  • The well in the middle of Monteriggioni Piazza Roma
  • Magnificent city walls that protect the Commune di Monterrigioni!
  • Exterior pathways flanked with cypress trees that give way to incredible views of Tuscany

Self-Guided Walking Tour

Monteriggioni: Cosa Veder (“What to See?”)

As you explore Monteriggioni on foot, be sure to look for

  • Centro storico di Monteriggioni – the historic center of Monteriggioni
  • Porto Franca – the gate facing Rome
  • Porto Florentina – the gate facing Florence
  • Medieval homes in the Largo Fontebranda
  • Museo Delle Armature – a museum of ancient arms and armor that you can try on!
  • Chiesa di Santa Maria Assunta – the small medieval church where you can light a candle for a loved one
  • The walk along the the fortress walls – you’ll pay a small fee but the views are worth it
  • Fattoria Castello Di Monteriggioni – the Monteriggioni winery in Piazza Roma; their “entoca” (wine library) is the first winery inside the castle. Schedule a tour, wine tasting, or purchase quality wines and oils.

Monteriggioni Restaurants – Where to Eat

Don’t expect a wide selection of restaurants in Monteriggioni, but you will find good pizzerias, gelatarias, and wine. 

Four restaurants located right in Piazza Roma you might consider are:

  • Osteria Antico Travaglio – this is a great place for some house-made pasta and gelato out in the piazza, blacksmith forge, or stable.
  • Il Tagliere Medievale – Enjoy a panini made with fresh bread, charcuterie platter, or caprese salad here.  (Tip: There’s air conditioning upstairs and free wifi.)
  • Ristorante il Pozzo Monteriggioni – authentic Tuscan cuisine with good food and wine and a friendly staff.

Shopping in Monteriggioni

Monteriggioni’s economy is mainly based on agriculture and wine. (You can’t help but swoon over the picturesque vineyards surrounding the castle!).

The artisans in Monteriggioni are known for their pottery, wooden and marble artifacts, so you might pick up a few souvenirs to remember your visit. And of course, did I mention Monteriggioni wine?

Monteriggioni Chianti Wine – Photo by Giulio Nepi – Wikimedia CC

Where to Stay in Monteriggioni

Since Monteriggioni is a sleepy little town in Tuscany, it may be easier for you to book a hotel just outside of town. This way, you can quickly and easily visit multiple Tuscan villages while staying within the region.

Therefore, here are a list of some of the best hotels both in and around the gorgeous of Monteriggioni.

  • Villa Lecchi Hotel Wellness – Located in the nearby region of Poggibonsi, this hotel is a mere 15-minute drive from Monteriggioni and is nestled atop a hill in a former 18th-century villa. Step inside and you’ll enjoy a charming, stone building with two outbuildings and a series of well-appointed rooms that feature canopy beds, fully restored frescoes, and spacious sitting areas. Guests can also take advantage of an upscale restaurant that overlooks a garden terrace, an outdoor pool, and a spa with an indoor pool and a luxurious Turkish bath.
  • Borgo Gallinaio – This charming 3-star hotel sits inside the center of Monteriggioni and is the perfect place for a relaxing getaway amidst the beautiful hills of Tuscany. Not only is there an Italian restaurant on-site that is exclusive to hotel guests, but stately rooms here offer sweeping views of the vast countryside – in addition to elegant decor, free WIFI, luxurious bedding, an in-room safe, a mini-bar, and free WIFI. Some guest suites even feature a working fireplace, making this the perfect place for a cozy stay in Tuscany.
  • Contessa Ava dei Lambardi – This cozy, rustic inn in the heart of Monteriggioni sits inside an old monastery and offers clean, comfortable, minimalist-style rooms that are well-priced – making this the perfect place for a quiet getaway. There’s also a high-end restaurant in town and modern bathroom facilities that guests can use, as well as free WIFI and old-world style decor throughout the entire hotel. So, if you’re looking for a no-frills, reasonably priced stay then this is the hotel for you.

Final Thoughts on Monteriggioni, Tuscany

While this tiny town within fortress walls can be explored in just a few hours, Monteriggioni is the kind of place that will leave an impression on your memory for a lifetime. You might even decide to stay overnight in one of the beautiful Monteriggioni hotels and villas.

No matter how long you spend, if you plan to be in Tuscany and are scouting for medieval charm steeped in a rich history, you will certainly find it in Monteriggioni Italy.

And if you enjoy Tuscan Hill Towns and are looking for another easy day trip from Florence, click here to learn more about Fiesole, Italy. Not only is it rich with Etruscan history, but It’s the perfect place to catch the best sunset of Florence!

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This article is a collaborative post and may contain affiliate links. As always, all opinions expressed are my own. For more information, please see the following Disclosure.

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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.