Is Monteriggioni Real or but a dream?
If you're driving northwest of Siena on the Via Cassia (SS2) Monteriggioni will appear like an apparition on the hills overlooking the superstrada. It is indeed real. But the fact it's one of Europe's most well-preserved walled city may convince you what you are seeing is undoubtably fake--especially if you've never heard of the medieval village. In this case you will likely turn your attention to the GPS, struggling to find the name of this amazing place. Expect honking horns as you wallow along the roadway.
Montereggioni is "cute" but you won't catch me using this terminology. It's a defensive structure that's held off Florentine attacks of the 11th century. Its 10 meter wall fortified by 14 watchtowers can be seen for miles around.
Thus preserved, it has served as a background for movies requiring a typical medieval city as background.
Monteriggioni is located in the province of Siena, 14km to the northwest of the city of Siena (54km from Florence). While it can be done as a day trip from Siena, you might be better off staying the night--Monteriggioni is much more evocative when the tourists leave late in the afternoon and you can sit in a courtyard sipping a glass of Chianti. Monteriggioni is surrounded by vineyards, and is known for its wine production.
The village is slightly elliptical in shape with two gates (a third has been plugged). The major gate tourists will use when coming from the parking lot, Porta Franca, owes its name to the Via Francigena--Monteriggione was a major stop on the pilgrimage trail from Cantebury to Rome. The Romanesque Church of Santa Maria Assunta will offer assistance with housing for modern pilgrims traveling the Francigena pilgrimage route.
Monteriggioni was a sleepy village of farmers and sheep herders as late as the 1960's. Today it exists entirely for tourists and pilgrims. You'll find wine shops, a tasting room, restaurants and hotels in the small village, mostly around the piazza Roma. The darth of real inhabitents is not neccessarily a disadvantage, although it's nice to see some locals puttering about once in a while.
The village's relative calm is broken by the big summer festival celebrated in Monterigioni called Festa Medievale, the Medieval Festival held in mid July. It is one of the most renowned of its type in Italy, featuring characters in medieval costume, ancient musical instruments, minstrels, and shows.
You can visit the little museum, dance a bit on the walls, and see the church. After that, it's all about sitting in the shade in the piazza and relaxing, or tasting some wine in the tasting room. If you're traveling with someone who just has to rush around for 18 hours a day seeing everything, Monteriggioni is the place to take them for a day of chilling out.
If you want to get out of town, the Abbadia Isola is 4km away, accessible by car or by foot. It's a Benedictine Abbey located at the foot of Montemaggio Mountain, founded in 1001 and fortified in 1376 against those Florentine assaults.
What to See & do in Monteriggioni
If there is a place of assembly of the masses where one might find a restaurant and shops, it's around the Piazza Roma across from the church.
The late Romanesque church of Santa Maria Assunta faces the piazza Roma. It was consecrated sometime between the building of the defensive walls (which can be seen in the background of the picture above) (1213) and 1235, when the peace treaty between Siena, Florence, and Poggibonsi was signed here. Santa Maria Assunta's association with pilgrims tracing the Via Francigena route continues to this day. A notice on the door offers lodging assistance to pilgrims. To the left of the church as you face it is the tourist information office, where you can obtain lodging and other information on Monteriggioni.
If you're curious about the armor that the big boys in the watchtower might wear in times of attack, there's the little Museo Delle Armature to enlighten you. If you're good, they might let you touch or even wear samples of period armour and weaponry.
And if you've had a big meal in the Piazza Roma it might be good for you to talk a walk around the walls. It's not all that big of a belt around the little village--and you'll have great views of the Val di Elsa.
Map Showing Monteriggioni
Finally, here is how the site looks like from above on a Google map.