Fly Alitalia to Milan and change planes for the hop to Florence. The airport there is small and relatively uncrowded; renting a car and finding the autostradais much less of a hassle than it is at Fiumicino in Rome. On the other hand, flights from the United States to Rome are nonstop. Either way, it's less than two hours by car to the southern part of Tuscany.
Fabrizio Caffarelli has two luxurious farmhouses for rent outside San Casciano dei Bagni. He can be contacted via e-mail at email@example.com or by phone (39-0578/245-001, fax 39-0578-245-600; from $7,350 per week). (He speaks English.) For a larger selection, consult www.holiday-rentals.com (from $1,000 per week). Another reliable and well-priced source for renting a restored casa colonica in the area of Montalcino and the Sienese crete is TuscanHouse (www.tuscanhouse.com). Spacious, fully equipped villas with a pool and maid service start at about $2,500 per week.
A less expensive but delightful family alternative is to stay at an agriturismo in rural Tuscany. Some are mini-resorts, all are part of working vineyards or farms that rent individual rooms or apartments. Most serve breakfast, and some have excellent dining.
Il Poggio, near San Casciano, is set on a spectacular hillside in the medieval village of Celle sul Rigo. The facilities include archery, tennis, soccer, two pools, a first-rate riding stable, and two restaurants, one serving excellent Tuscan cuisine, the other pizzas—and the only hamburgers we found in Italy(39-0578/53748, fax 39-0578/53587; e-mail firstname.lastname@example.org; from $776 per week).
Le Ragnaie, outside Montalcino, is a serene and low-key vineyard inn that produces its own Brunello. It has pleasant rooms and apartments, a pool, and a good restaurant. In season you can participate in archaeological digs on a nearby Etruscan site. (phone and fax 39-0577/848-639; apartment for four $630 per week).
Ristorante Daniela 7 Piazza Matteotti, San Casciano dei Bagni; 39-0578/58041; dinner for four $75. This family-run restaurant became our own "mess hall."
Ristorante La Torre Monte Oliveto Maggiore; 39-0577/707-022; dinner for four $50. If you plan to visit Monte Oliveto Maggiore, reserve a table for lunch here.
Ristorante Tonino 1 Piazza Garibaldi, Cortona; 39-0575/603-500; dinner for four $90. A venerable institution, with a panoramic terrace bar that looks out over the Val di Chiana.
Locanda Sant'Antimo Castelnuovo dell'Abate; 39-0577/835-546; dinner for four $40. Good Tuscan fare.