You can park your car in either of the two parking lots, Then you walk into the village via a very large gate between two towers in the city wall. If you continue straight ahead, you will walk through the entire village (very quickly; it's small) and there is another gate on the opposite side of town. This is a great starting point for a walk or hike in the lovely Tuscan countryside. Generally, you enter the eastern gate and leave the western gate. You can walk around the entire walled village . . . or simply back to parking if you turn right leaving the western gate.
The first and second week of July is "The Monteriggioni Medieval Festival" and you can get all the info from the Office of Tourism in Monteriggioni at the web site listed below.
We were there a month early so didn't see it, but they have characters in costume, dancers accompanied by old instruments, minstrels, shows and torchlight parades. It sounds like great fun and might be fun to spend the Saturday night at the local hotel within the walls. I suspect you would have to book well ahead of time.
The views from the city gates are spectacular and the views outside the wall are too. However, climbing the ramparts gives you more height so more view. The fun part is that you can look both ways. You can look at Chianti outside the walls . . . just like all those photos you've seen . . . or you can look down inside the walled city and see ladies hanging out their laundry, people and activity in the piazza, gardens and back yards.
It is great fun to look out and see all those yummy Chianti grapes growing in the fields.
If you look at the third photo, you will see a lot of cars in the Piazza. This was a touring group of vintage cars, including a Model A Ford and several vintage Mercedes and Jaguars. They drove through the city gate and parked in the piazza despite the "Pedestrian Only" signs. Within 10 minutes, the police arrived and escorted them back out the gate. There is pay parking immediately outside the gate so I don't know why they didn't use it. There is also free parking at the foot of the hill. We watched it all from the ramparts.
This church located in Piazza Roma, was built in the 13th century. It has Romanesque-gothic features and is composed of a single nave with apse. The facade is made with travertine, is dominated by a portal which is surmounted by an archivolt with a slightly gothic arch. On high there is a small round window framed in brickwork.
The town of Monteriggioni is very simple: there is a main road that connected the two gateways of the wall: Porta Romea which connected the town to Siena and Porta San Giovanni which connected the town to Florence.
The wonderful and interesting fortified wall of the town was built between 1213-1219 to protect the town of Siena from Florence. The wall was rebuilt in 1260 after the smashup made by Florence in 1244. The wall is all around the town and it is 570 meters long. Along the wall there are 14 towers.
If you bother to hover around the side streets of Monteriggioni, you'll notice this house (it's built of bricks of different colour). It happens to be the oldest in Monteriggioni, dating back still from the 1200s.
If you observe well you can recognize some typical medieval architectural themes, such as the clay stone arches above the main door and some windows, and the large stones holding the door shape.
Porta romea was built in the year 1213, as the rest of the walls. It is the gateway to Siena along the old Via Francigena, or the road to France, along which the village was built already in Roman times.
It was the Sienese, however, who transformed the village into a fortified castle, due to its strategic position on the way to Florence. No wonder that the gate towards Siena looks much more majestic that its northern counterpart.
The gate carries a stone inscription commemorating the building of the walls between 1213 and 1219 (see my other tip), and is likely to be your gateway to the castle nowadays since the parking places are located just outside.
From inside, the view is excellent over the smooth landscape of the Sienese hills.
The walls were built for the first time between 1213 and 1219, and re-inforced several times thereafter until 1545.
The walls are 570 metres long and boast 14 well-kept towers, seven of which were heightened after the original construction project took place.
A stone inscription over the main gate (Porta Romea, see my tip) commemorates the building of the original walls.
The castle lost its strategic importance once Florence won their 300-year war with Siena, and it wasn't touched anymore, thus preserving its original face until today.
The walls completely encircle the town and have 14 heavily fortified towers which were built to keep out invasion from Florentine armies. It looks like you can walk along some parts of the walls as some wooden walkways are positioned along the top but when I was there it didn't look like this was possible.
The main square of Monteriggioni is called Piazza Roma. Here you can see some buildings made in the 13th century and the nice church.
This charming square is the only square in the town. Most of the town's shops and restaurants surround the square as well as the town's only church.
Porta Romea is the main gateway (well there's only one other!) in the encircling wall. The gate is the first thing you'll come too when you walk up from the main car park.