Please also see this page for tips on Florence.

Siena (pictures)

Siena is my favorite city in Tuscany. There are really two main sights here – the cathedral and the Piazza del Campo, or central piazza.

The cathedral is quite different from the one in Florence – instead of a great red dome, there’s a black and white stone tower. The inside is amazingly opulent, some might say overdone (the parade of pope’s heads on top of the columns in the central nave are over the top). But the real glory of the cathedral is the floors, which feature about 60 stone tile paintings. Also not to be missed is the Piccolomini Library, which is reached from inside the cathedral (small admission charge). Piccolomini is the family name of the Sienese family of Pope Pius II, whose life is depicted in murals inside the library. The murals were done by the famous painter Pinturicchio, and his even more famous pupil, the young Raphael. Raphael paints himself in one of the frames – he’s the guy with the tight pants, one hands on his hips and attitude (some things never change).

The Piazza del Campo is the site of a famous horse race held twice each summer called the Palio. The race features 10 horses, each representing a contrade, or district, of Siena. (Each district has its own animal symbol – dragon, turtle, snail – which you can see on street lamps and buildings in each district as you walk through the town.) Since the race has no rules, betting is heavy, and the Piazza is canted inward, the horse race must be something. The Palazzo Publico (city hall), at the far side of the Piazza, has a small museum featuring the Allegory of Good Government, a painting you’ll recognize as soon as you see it.

The bell tower features a she-wolf suckling Romulus and Remus (Remus is the legendary founder of Siena, as Romulus was of Rome).

Sit in one of the cafes in the Piazza and order a slice of panforte (richer than bread, lighter than fruitcake).

Orvieto (pictures)

Technically, Orvieto is in Umbria, not Tuscany, but go anyway.

Unlike Florence or Siena, Orvieto is a hill town, with the cathedral on top of the hill. The cathedral in Orvieto you will immediately recognize as the model for the one in Siena. It is somewhat less opulent, and more beautiful for it. Visit the chapel of San Brizio inside (separate admission, and you have to buy a ticket at the tourist bureau across the street). The mural of the last judgment, by Luca Signorelli, is believed to be the model for Michelangelo’s famous mural in the Sistine Chapel. (Signorelli is one of the greatest artists you’ve never heard of, by virtue of the fact that most of his stuff is splashed on Italian walls.) The screaming woman being flown down to hell on the backs of a demon is Signorelli’s girlfriend, who left him while he was doing the painting. Particularly interesting are the skeletons popping up out of the ground on Judgment Day, waiting for their new bodies. Some young skeletons are just relaxing against a fence, handbones on hipbones, looking like they were lifted right off a Grateful Dead album cover. Some things never change.

If you’re driving, there is a parking garage with an elevator about half way up the hill. If you’re feeling lucky, there’s a small parking lot on the top of the hill, right next to the cathedral.

Orvieto is famous for its white wine, called, oddly enough, Orvieto. Most of the wine being made today is very dry, to suit modern tastes, but see if you can find the older version, amabile, which is ever so slightly sweet.

Pisa (pictures)

Pisa was heavily bombed (by us) during the war, and as a result most of the city is not very interesting. Fortunately, the Campo dei Miracoli (cathedral square), unusually located in a corner of the city rather than in the center, was spared. The Leaning Tower was recently reopened after some major work to shore it up. Climbing it is well worth the experience, but watch that vertigo. There are places where your eyes will tell you that you are going up, while the gravitational pull is strictly down. If you’re prone to motion sickness, be careful.

The baptistery and cathedral are also well worth a visit. The Pisans had a style all their own, which has obvious Moorish influences, and the pulpit of Nicola Pisano is a wonder.

Lucca (pictures)

Another city with a unique architectural style, and a high school named for Niccolo Machiavelli. Famous for its olive oil.

Val D’Orcia (pictures)

The Val D’Orcia is not a city, but an area with a number of small towns worth a visit.

Montalcino is famous for its red wine, Brunello. The town is wall-to-wall wine stores, offering tastings at various prices; the best values are probably at the town-run cooperatives, rather than at the private wine shops.

Sant’Antimo is an abbey church with a small group of monks who sing Gregorian chant at intervals throughout the day. The décor is very Spartan, which will probably come as a bit of a shock if you go there after a series of opulent Italian churches.

San Quirico D’Orcia is a pretty small town famous for once being the base of Frederick Barbarossa, the red-bearded German who conquered Italy in the 11th C. The town center has a small northern style church, whose façade is decorated with Celtic Loops stonework hundreds of miles from their normal habitat. If the church is open, behind the altar is a small room with some beautifully inlaid wood panels.

Pienza, one of the first planned towns, was designed by the same Pope Pius who sponsored the Piccolomini Library in Siena Cathedral (Popes were Renaissance men in those days). The main square in Pienza was the one used for the small Italian town depicted in The English Patient (although the statue that blew up in the movie was the moviemaker’s invention). Pienza is famous for its fresh Pecorino cheese, which is totally different from the aged, dry Pecorino usually sold here, and well worth sampling. (If you like it, fresh Pecorino is usually available at Ferrari’s delis located throughout the Bay Area.)

Monte Oliveto Maggiore

This is a monastery where rich old Sienese men who were tired and jaded went to reclaim their spirituality before they died. They were willing to give up their creature comforts to live the monastic life, but not their art. The cloister is decorated with elaborate murals of the life of Saint Benedict, done mostly by another great artist you’ve never heard of, Il Sodoma, and partly by Luca Signorelli. The monastic library, which is not always open, has some wonderful examples of inlaid wood furniture, including some decorated with a greenish-colored wood they still haven’t been able to identify. The monastery is not far from Siena, but hard to find – get a good map. If you find yourself in Aquaviva, you’re hopelessly lost.

Cortona/Montepulciano (pictures, more pictures)

Cortona was the home of Luca Signorelli (in the 15th C) and Frances Mayes, author of A Villa in Tuscany, today. There is a small museum, hard to find, but with some wonderful paintings by Signorelli and by Fra Angelico. But Cortona is a wonderful small town to just be in, and to walk around. Not far away is Montepulciano, another famous wine town with a truly impressive hill. Check out the Etruscan funeral urns that are used for building blocks. There is a town-run cooperative at the top of the hill where you can taste the local wines, for a small charge.

San Gimignano (pictures)

Interesting because most of its towers are still standing; most of the others in Tuscan towns have long since fallen down. A small town, it tends to be overwhelmed by tourists.

Assisi (pictures)

Again we are venturing into Umbria.  The recently restored cathedral is indeed a wonder, but the church is a pilgrimage site and all those shops selling ticky-tacky religious articles can be off-putting if you’re not prepared for it. This cathedral is run directly by the Vatican, and there is a dress code (see below).  If you go, you might want to visit San Damiano and the Eremo (hermitage) of St. Francis.  Both are a bit out of the town center.  They exude a bit more of the ascetic character one usually associates with St. Francis.

Perugia (pictures)

Interesting old town at the top of another Umbrian hill. Nice art museum with many Peruginos.

Spello, Montefalco, and Spoleto (pictures and more pictures)

If you are venturing further into Umbria, you might want to visit these towns.  Spello is one of Ted’s favorite places even though there are few special sites there.  Montefalco is a lovely town with top notch wine and very special frescoes by Gozzoli.  And, Spoleto is home to a beautiful church with frescoes by Lippi, a well-known music festival, and some gorgeous countryside.