Robin Garr wrote:If you don't mind, though, it would be great if you'd post a few reccos here for the public record.
Well sure. My wife and I made Siena our base for a week-long visit to Tuscany during our honeymoon in 2001. So, a caveat: most of my recollections date back to an extremely happy time five years ago. On the other hand, little seemed to have changed when we returned on a day-trip with another couple last June.
For orientation purposes, you might think of Siena as a steep-sided bowl. At the bottom lies the “Campo,” one of the most celebrated public spaces in Italy. It’s a roughly semicircular piazza, with a town hall and bell tower on the flat side and cafes lining the rest of the perimeter. Pedestrian streets and alleys wind up the sides of the bowl. Many of the Renaissance buildings along the way have street-level shops and are connected by enclosed upper-story bridges. Legend has it one can walk around the entire city center and never set foot on the ground. For a pageant known as the “Palio,” the Campo is converted into a racetrack. Marchers and jockeys from the city’s historic neighborhoods compete twice a year for bragging rights.
My wife and I stayed at the local outpost of the Jolly Hotel chain, at the top of one bowl side, right across from the main inter-city bus stop and a 10-minute walk from the Campo. It was perfectly serviceable, 70s moderne in style, with good breakfasts and view into Siena’s soccer stadium. I’d stay there again, primarily for the location. It’s also a short walk from a church with two of the town’s creepier attractions—the preserved head and thumb of St. Catherine of Siena, who died in the 14th Century.
It’s hard but not impossible to get a bad meal in Siena. I highly recommend Ristorante Guido, on small side alley about halfway up the bowl from the Campo to the bus stop. Great food, fine local wine list, very good value. My wife still considers the carpaccio served on arugula with ribbons of shaved parmesan one of her favorite dishes of all time. We ate there twice. Just off the Campo, to the right of the Town Hall, is La Torre, a somewhat rustic, family-style place that can be a lot of fun. When my wife asked for a menu, the chef (who was our waiter that evening), said “I am the menu.” Much of the food is roasted in a wood-burning oven. My roasted pigeon was served with its head on.
Off the Campo to the left of the Town Hall runs a street with several restaurants, the more popular of which are on the left side. On the right, there’s Ristorante Nello, to which I will never return. Truth be told, the food is outstanding, but the chef-owner is a colossal jerk who tried to publicly humiliate one of my companions for putting too much balsamic vinegar on her salad. Even his staff was offended. I’m not surprised that every other place on the street is more crowded. I'll check my notes for other possible restaurant recommendations and add them later if I find any.
Any of the cafes on the Campo are wonderful spots to sip a drink and watch the world go by. Smaller and more local, Caffe del Corso sits halfway up one of the main streets climbing the side of the bowl. In the early evening, they seem to pour their way through a case of prosecco an hour.
For any wine lover, a visit to the justly famous enoteca inside the walls of the old fortress is a must. Wines from all over Italy are featured, with rotating offerings by the flight, IIRC. I didn't eat there, but they're reputed to have lovely small dishes. Siena is also a relatively short drive from several lovely wine towns, including Montalcino (with its own fine enoteca), Montepulciano, San Gimignano, and the various stops along the “Strada di Vino” that winds through Chianti. Of the wineries we visited, Altesino (north of Montalcino) and Castello di Brolio and Badia a Coltibuono (both in Chianti) were most interesting destinations in their own right. Badia has more or less restored an old hillside hamlet, has a superb restaurant, and offers cooking classes.
Rental car is the best means of transport for winery-hopping, but there are probably buses to the larger towns. Also accessible by bus from Siena, I think, is the nearby Monteriggioni, a jewel-box of a little town (I think I'm stealing that phrase, but I can't remember from whom)that would make a great lunch destination.