A Pit Stop In Monteriggioni: From Florence to Siena

Getting there

The best way to reach Monteriggioni is to drive. While the signs to Monteriggioni are well marked, upon arrival, parking is a little difficult.

There is no parking inside the castle walls. At the bottom of the hill from Monteriggioni is a clear road sign showing you the dirt parking lot just off of the Strada Comunale di Monteriggioni. To enter the parking lot, you must first take a ticket that stamps the date and time of your arrival. Keep the ticket in your car, you validate it at the end of your visit at the validation machine that is located near the exit. You cannot validate the ticket while in your car (it is not a drive up validation booth), so collect the ticket from your car and bring the ticket to the validation booth to be validated. Then you can get in your car to leave. However, this may be temporary, as it seemed there was some work being done on this system.

The validation machines are located to the right of the exit in a small wooden stand. On the validation machine, you will find step by step directions in picture form that can help you validate your parking ticket. There was a credit card option to pay; however, having cash on hand will make the process easier.

From this parking lot, it is a short uphill walk to the gate (Porta Roma) that leads into the city. You will not get lost as the path is well labeled. The charm of Monteriggioni lies in how easy it is to explore the whole town in just a short time. There are only three main streets that run north south through the town and a handful of cross streets. But remember to wear comfortable shoes, you would be surprised at how tired your feet can get after an hour or two.

Within the walls of Monteriggioni

There are two gates that lead into the walled city of Monteriggioni. The southern facing gate is called the Porta Romana, as it faces Rome. This is the gate that most people enter through, as the paths from the parking lot lead here. The other gate is located at the other end of the town. It is a northern facing gate and is called the Porta Fiorentina, because it faces the city of Florence.

Be sure to stop and take pictures before you enter the city. There is something about Monteriggioni; it is as if you can smell the history in the air. Over the years, there has been subtle restoration done, but this fortress that was built to keep people safe from invaders in the 13th century, still stands strong.

A few feet inside the main gate, you’ll come across a courtyard on your right. Inside, you’ll find an old covered wagon that doubles as a ticket booth. This is where you can purchase tickets to climb to the top of the walls of the castle. At the time of writing this article, the cost for one adult ticket to walk the walls was 3 EUR, 3.37 USD. Two sections of the wall, one at either end of the town, have patricians built in so you can walk along the walls. From up here, you’ll be able to see the countryside just as the guards who paced this area hundreds of years ago might have.

Remember to bring your camera. Once at the top of the walls, you can see for quite a distance. And you will find the dreamy Tuscan countryside stretched out before you.

Shopping and eating

If you’ve climbed the walls of the city and viewed the stunning Tuscan countryside, then it’s time to sit in the Piazza Roma and let your imagination run wild with what life must have been like 600 years ago. Cars are not allowed within the castle walls as the original medieval streets are too narrow for them. But this only adds to the historic atmosphere and allows travellers to be transported back in time without disruptions of modern life.

Pull up a chair in the outside seating area of Cafe Antico Travaglio and order a cappuccino. From this vantage point you will have a perfect view of the Church of Santa Maria Assunta, which was built in the 13th century, at the same time as the city walls.

You will feel like time has slowed down in this small town. Tourists meander, taking their time to explore. You will find picturesque scenes around every corner. Because the town is so small, it is easy to explore it in its entirety. You will discover a handful of shops. Most of them sell goods made by local artists. On the Via I Maggio, you will find Artes, where they sell hand-woven fabrics and knitwear made on the premises. On the same street is Rosso Ramina, where darling handmade ceramics are crafted and sold.

If you are looking for a great souvenir from this medieval castle town, stop by Fattoria Castello di Monteriggioni for a bottle of wine made from grapes grown in nearby vineyards. If you don’t have room to take a whole bottle home, you can always do a wine tasting there.

La Biottega dei Sapori Francigena, is a darling store tucked at the end of Via Matteotti, to the left of the northern facing gate. They have locally made honey, dried mushrooms, pasta and balsamic vinegar for sale.

If you arrive at Monteriggioni in time for lunch, there are several restaurants for the choosing. The Osteria Gelateria Antico Travavaglio in the Piazza Roma offers a wonderful baked lasagna that pairs deliciously with their red house wine. At the end of the PIazza Roma, is the Ristorante il Pozzo. The restaurant has outdoor seating, indoor and garden seating and a friendly service.

The handful of restaurants in Monteriggioni all have their menus and prices posted outside so you can compare; however, do note that it might not be worth meandering around for too long as they are all very similar to each other.

While there is no need to make reservations for lunch, if you plan on being in town for dinner, it might be a good idea to reserve a table. This scenic town is often a destination during peak season for an evening meal.