The Medici's secret passage on the Ponte Vecchio

An amazing fact about the Ponte Vecchio over the Arno (the only bridge the Nazis did not blow up in WWII), is that there is an amazing collection of paintings and portraits hidden behind the upper walls on the bridge. A corridor, called the Vasari Corridor, after the architect, was constructed for Cosimo Medici to safely commute the half-mile from the Palazzo Vecchio, his office, to the Pitti Palace, across the Arno. It constitutes the longest single passageway of paintings and portraits in the world. And if you wonder why so many gold and silversmith shops are concentrated on the Ponte Vecchio, it's because Cosimo's son Fernando had the butchers and tanners removed from the bridge, because of the stench, and replaced them with gold and silversmith shops. It is possible to see this incredible art treasure/private walkway of the Medicis. Check out this link: http://weekendafirenze.com/exclusive_tours/uffizi_vasariano_eng.php?lang=en

The Palio in Siena

Siena's Palio, the centuries-old horse race run twice each July, because there are too many contradas (neighborhoods, but intensely so) for one race, is a truly amazing event. See http://www.ilpalio.org/index_english.htm ] And the pagentry and festivities go on both days before and after the race. What a party it is! As for the race, the horse wins, not the jockey, and is the hero. The jockey is inconsequential. There are no rules to speak of. Jockies may lash the other jockies with their whips, and the horse can win even if the rider falls off. The horses are blessed inside each contrada's church. Many Siennese couples have their weddings during Palio week. A wonderful film of the Palio can be found on the DVD of "A Summer's Lease", a 1989 BBC miniseries seen in the U.S. on Masterpiece Theater. http://www.tvdvdreviews.com/sumlease.html It is a splendid movie about a family's month in a villa near Siena, and John Gielgud, among others, is hilarious in it, although the plotline is a murder mystery. It really captures the languid and dreamy quality of a month in the Tuscan countryside.

Why Italy?

"Whenever I go anywhere but Italy for a vacation, I always feel as if I have made a mistake. All too often I have changed my plans and left - from a ski resort in the French Alps, a mountain town in Switzerland, a country house in Provence - to get to Italy as soon as possible. Once across the border I can breathe again. Why bother to go anywhere, I think in those first ecstatic moments of reentry, but Italy?
What do we find in Italy that can be found nowhere else? I believe it is a certain permission to be human that other countries lost long ago. Not only is Italy one of the few places left where fantasy runs unfettered as Luigi Barzini said in "The Italians", 'even instruments of precision like speedometers and clocks are made to lie in Italy for your happiness'; it is also one of the few places that tolerate human nature with all its faults. Italy is the past, but it is also the future. It is pagan, but it is also Christian and Jewish. It is grand and tawdry, imperishable and decayed. Italy has seen marauding armies, Fascists and Communists, fashions and fripperies come and go. And it is still, for all its layers of musty history, a place that enhances existence, burnishes the moment...."
---Erica Jong, from "My Italy"

Florence view from San Miniato

For me, the finest view of Florence is not from the Boboli Gardens, or Piazza Michelangelo, but far above the latter, from the church and monastery/cloister of San Miniato al Monte, run by Olivetan monks. You go up the winding road past Piazza Michelangelo to the top of the hill, climbing the last 75 steps or so, to the basilica of San Miniato. (If you saw the Brian de Palma movie, "Obsession", with Cliff Robertson and Genevieve Bujold, inside this church is where key scenes in that movie take place.) The view of Florence from this spot is magnificent. The Romanesque church and monastery are also magnificent, and worth an hour or two of your time. See: http://en.wikipedia.org/wiki/Basilica_di_San_Miniato_al_Monte

And if you are there around 5 o'clock in the afternoon, you can go inside the church and hear the monks wnderfully singing Gregorian chant....just sit on the steps in front of them and listen quietly...they don't mind. These monks make several famous liquors, which you can buy at a shop there.

There is also a fascinating cemetery in front of the church (the creator of Pinocchio is buried there, as well as the poet/author Luigi Ugolini), and the defensive walls around the church were built originally by Michelangelo.

Saint Catherine's head in Siena/the rest is in Rome

The preserved head of Italy's co-patron saint, Catherine of Siena (the other being St. Francis, of course), can be seen in the church of San Domenico, a cavernous and bland building it is too, as you walk toward the center of Siena from the city's tourist parking areas. You can't miss it. You will find Catherine's head behind glass in a tabernacle on the altar in a chapel dedicated to her inside the church. Her head seems so small. See www.italyguides.it/us/siena_italy/san_domenico/basilica_of_san_domenico.htm )
The rest of Catherine is buried in Santa Maria sopra Minerva church, on Piazza della Minerva (which is adjacent to the Pantheon), in Rome. This church was built on top of a Roman temple to Minerva, hence the name. Fra Angelico is also buried in Santa Maria sopra Minerva. There are also 5 Popes buried here. This is where Bocelli's "Sacred Arias" concert was filmed a few years ago, by the way.
( http://en.wikipedia.org/wiki/Santa_Maria_sopra_Minerva )

Rent a car (or a driver)

The best way to travel Tuscany and/or Umbria is to rent a car. This assumes you have several days to devote to touring. There is no better way to see the towns and villages and countryside. AutoEurope ( http://www.autoeurope.com/ ) is a U.S.-based company that has always been the cheapest, easiest and most dependable rental company for me. You book your rental here, and pick it up from Europcar (or sometimes Avis or another agency). They don't try to take advantage of you (once, during a spot of confusion, we dropped off a car in Venice, on the sidewalk in front of a Europcar booking office having no place to park cars, rather than at the Venice airport, where it apparently should have been dropped. We pointed the car out to the Europcar duty person there, quickly handed him the key and our papers, and rushed off to where our wives were holding a boat to take us to our hotel. The fellow kept saying but, but, but... But they never billed my credit card anything additional for dropping at the wrong place).
Be sure to book your car or van before you leave the States...it's much cheaper than doing it after you get there.
I think Italian drivers are terrific (they go by eye contact with you regarding right of way and at intersections, I find), and it is always a pleasure for me to drive there. But don't try to drive in Rome, except to perhaps pick up your car at Fiumicino Airport to drive north.
And of course, always have a good road map with you.
If you are limited in the time you have to see the hilltowns and countryside, you may want to hire a driver/guide to take you on day trips. They can save you a ton of time. Once we hired a driver to take us to Siena for the day, from Florence. He whizzed us down there in his Mercedes, and delivered us to very steps of the incredible cathedral at Siena ( http://en.wikipedia.org/wiki/Duomo_di_Siena ). On our own, we would have had to come in the crowded tourist "front" way, parked, and walked for 30 or 40 minutes to get to the cathedral. But our driver took us in the back gate of Siena, which would have been nearly impossible for us to learn about and find. Plus, he parked where we would not have, and stayed with the car, in case it had to be moved. Most hotels will arrange a driver for you. And a driver will also provide local color and anecdotes you don't find in the guidebooks. They are well worth the money if you don't want to drive, or only want to do one or two day trips. Of course, there are group day trips to the most popular places. Your hotel or travel information office (look for the "i" sign on a building) can help you there too.