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In the increasingly fashionable Maremma region is überchef Alain Ducasse's new (2004) 1,250-acre estate—the former residence of Leopold II, Duke of Tuscany. Of the 33 rooms, those in the Villa are grander than the fattoria (farmhouse) ones, but all have exquisite decor with heavy silk drapes, Louis loveseats, chandeliers, pillars, gilt-framed mirrors and fireplaces—even the bathrooms have posh TVs and chaise lounges. Another highlight is, of course, Trattoria Toscana, Ducasse's restaurant in the granary, where you can also sample the estate's wines and olive oils.
61, Strada della Vittoria. 53042 Chianciano Terme, Siena
The late writer Iris Origo's estate, now run by her daughters, is a working farm, a cultural center and a collection of idyllic rental apartments and houses in various 15th- to 17th-century farmhouses around the estate and the medieval castle, Castelluccio (site of the annual Incontri in Terra di Siena chamber music festival). Each residence has a private garden, a pool, antiques and a kitchen (with someone to cook for a modest charge). To top it all, this is a great touring base, and the geometrical gardens are not just gorgeous—they're famous.
GRAND HOTEL CONTINENTAL
Via Banchi di Sopra 85, Siena
Its pedestrian name gives no clue as to the ridiculous splendor of the 17th-century Palazzo Gori, right by Piazza del Campo. The place is lousy with frescoes, museum-quality art, massive crystal chandeliers and valuable antiques in the 51 rooms. Do splash out for a special one—the four-poster-bedded octagonal room or the two-level Tower Suite with its beamed aerie in the campanile. There's a winter garden courtyard restaurant and a huge brick vaulted medieval wine cellar where you can taste special vintages.