However, on a sunny winter day skip bar Orso and drive up to Monteriggioni itself. The medieval stronghold is visible already from the highway and similar to San Gimignano has been a landmark along the former pilgrim route since medieval times (and hence also got its mention in Dante's Divine Comedy).
The fourteen towers have been cut back and rebuilt through the centuries but the intact town wall is the real deal. The small town has several bars and restaurants. On a warm winter day a glass of Chianti Classico and a sandwich and platter with Tuscan cold cuts or cheeses from bar del Cerchio in piazza Roma will be perfect. Service isn't too welcoming and the selection of ingredients not as good as in bar Orso, but the outside sitting area in the beautiful square is perfect to soak up the winter sun and the beautiful outset of the square.
WHAT TO DO IN MONTERIGGIONI
If you explore Monteriggioni during high-season (from Easter to October) you may want to adapt the same tactics that I recommend for other small but overly popular tourist destinations like San Gimignano or Pienza. The car parking area close to the walls is bigger than the town itself, and Monteriggioni's vicinity to the highway turns it into a perfect stop-over for big tour groups. So come in the early morning for coffee in piazza or the late afternoon for an aperitif and stay for dinner. Like this you should be able to avoid most of the crowd.
Two different sections of the the town walls can be climbed, but be warned the grating leading up to the walls is totally safe but totally doesn't feel like it. However, the views make up for the wobbly experience. Just don't wear your highest heels and hold on to that skirt. I'm sure the local youth spends long summer afternoons lazing underneath in hope of a Marilyn Monroe moment.
A combined ticket grants you access to Monteriggioni's museum too. Its a small sight but families will enjoy it since kids can try on some knights' gear or fiddle around with a sword. The chain mail has been especially popular with mine.
Reproductions of medieval armors will make your 21st century teenagers yawn? Remind them of Monteriggioni's role in the Assasin's Creed videogames. I tried to look it up and don't understand any of it, but they'll probably know.
Combined tickets cost 4 € (children up to twelve years for free). We were rather surprised by the low ticket prices (especially of the town's fancy car park - 2 € for the day), which makes of Monteriggioni an easy to reach and surprisingly low cost stop if you travel by car.
Obviously if you travel on a budget avoid the retail opportunities in town. The ceramic shop on the main road (Via Maggio near piazza Roma, not that one really needs a map in Monteriggioni) sells a beautiful selection of Italian artisan pottery. Most of the hand made plates, cups and bowls are produced in Tuscany or close by. They are not cheap but make for beautiful souvenirs.
A few doors further on in via Maggio is the Tuscan shoemaker Pratesi. The leatherwear producer can be found in Siena, Pienza and Montepulciano too. The shops are often filled to the brim and not every model will convince. However, with a bit of patience you may be able to find a nice pair of shoes without having to spend a fortune.
WHEN TO COME: FESTIVALS
Monteriggioni is home to one of Italy's most famous medieval festivals. Each summer the town is taken over by jugglers, jesters, fighting knights and dancing maids. Markets are hold, games are played and street musicians entertain the crowd. Kids will love it! MONTERIGGIONI MEDIEVALE.
The 25th edition of the festival will take place on the first two weekends in July 2015: Friday, Saturday and Sunday July 3/4/5 and July 10/11/12. Tickets from 6 to 12 €.
If medieval festivals aren't your thing you'll know by now, that winter is my favorite time of the year for a lunch in Monteriggioni; the huge car park will be almost empty and you'll have the town to yourself apart of a few Italian tourists on the weekend.
WHAT ELSE TO SEE AND DO
Most travelers may head to Siena or nearby Colle Val d'Elsa from here. But church lovers should drive (or walk like the pilgrims would have) to Abbadia Isola. The former monastery with its church dating back to the 13th century were yet another stop on the Via Francigena, the famous medieval road that connected Rome to France and Canterbury.
Monteriggioni's tourist office website has maps for self guided hikes in the area. Rather walk with a guide? If you are looking for half- or full day walking tours around Monteriggioni, send me an email and I'll put you in touch with a certified nature and walking guide for the province of Siena.
The tourist office website also offers information on accommodation and last but not least an itinerary leading your youngsters to the sites featured in the Assasin's Creed game.