Chianti

There's a reason I choose to take students back to Siena every year . . . even though my heart belongs to Rome. The cities in the Chianti region of Tuscany are THE most charming, beautiful ones anywhere in Italy. I'll talk about a few here, but you really can't miss out, no matter where you choose to go.

West of Florence (not really Chianti territory) is Lucca, a small, walled city, famed for touring by bike. It's a rare spot where people will cancel their travel plans upon arrival, just to get more time in that city. Lucca and Siena are those kind of towns. Of course, west of Florence is also Pisa. Don't have much to say about that city (when the kids ask if, on their off-day, they can go to Pisa, I reply, "Go ahead."). I'm not a fan of tourist traps.

South of Florence is everything else.
San Gimignano is a must-do, even if only for a few hours. Visit the church where Sta. Fina is buried, and spend some time admiring the frescoes. Climb the Torre Grosso, and be sure to stroll up to the Rocca. And you HAVE to have gelato in the Piazza della Cisterna (it's the one on the west side of the piazza, with all the neon, which claims to have the best Gelato in the world - they really do).
Consider staying in Siena. It's absolutely magical, especially from sunset on. There are great museums, great palaces, and great people there. The food is incredible - one of my favorite spots is in the Piazza del Mercato - the one with the brown umbrellas - try any of the roasted meats or sausages on the menu. Also, the Pizzeria Quatro Venti (I think), located just down the street from the Duomo, right at the intersection of Aquila and Pantera, is a personal recommendation. (With this short mention, I'm doing no justice to this amazing city. Just know what kind of love I have for this town, that I return every year - this will be my sixth year to return to Siena for homestays. And my homestay mom is the best - Dina embodies all that is beautiful about Siena - her hospitality, her generosity, her full-hearted-ness, her amazing cooking skills . . .) Siena even has their own special Chianti, which, I argue, is better than the rest. It's grown in the crete Senesi, the clay fields just outside of Siena, which gives it a great flavor. Look for the black rooster on the label.
Smaller towns, like Montalcino, or Montepulciano, are surrounded by vineyards. All of them have their own beautiful charm and personality. One famed town is Cortona (Under the Tuscan Sun), but anywhere else similar is as wonderful.
If you go super-south in Tuscany, you'll love Orvieto. What a cute town!
Out east, consider going to Arrezzo - the Archaeological museum is actually built into the standing amphitheatre. And their art collections are incredible (not to mention, the churches). Really, a beautiful town, which carries many Tuscan qualities, yet has its own personality, too. Ever seen "La Vita e Bella"? Some earlier scenes were shot there.
In Siena, just to the south of Il Campo, is a tourist office, where you can book afternoon-long wine tours (2 - 7 PM), perfect for the wine experience (and with a pro). I'm sending my hugs out to Marco on this.
Never can say enough about the Tuscan wine country. Just be sure to enjoy your time there, and never allow the tourist rush to ruin your peaceful strolls!

Grazie,
Laura :)

P.S. Most of my monthly newsletters for the kids mentions something about Siena or Tuscany in them. Pillage all you'd like from the SPI 2009 group.