Some of the best of these establishments can be found on the winding road between Arezzo and Siena, in a slice of the Chianti region that has been turning out fine wine and olive oil for centuries. Local property owners have realized they can take advantage of tax breaks for farms while also profiting from well-heeled tourists. Though individual rooms for couples are available, accommodations are geared more toward families or groups of friends. Apartments are available to sleep four to 20 people.
Tenuta di Lupinari, a restored 18th century village amid 470 acres of sloping vineyards and olive groves, is a resort run by the Pellegrino family to accommodate as many as 37 guests. Strolling down a private dirt road on a recent sunny Sunday, family patriarch Antonio Pellegrino, 77, pointed out a small lake where visitors fish for trout and carp that can later be sauteed in oil made on site from locally harvested olives. Pellegrino showed off the cool confines of his 18th century stone olive press, which sees action only in November. During that harvest month, visitors can help pick the crop. He has noticed that American visitors are particularly keen on pruning the olive trees, though "they quickly realize it's serious work." For more relaxing activity, one can walk amid the vineyards and forests and explore the ruins of a medieval village.
Pellegrino's daughter Marianna provided a tour of the resort's amenities, at once comfortably modern and appropriate to the surroundings. Intimate indoor and scenic outdoor dining areas and a plush lounge with a fireplace were carved from what used to be the village horse stalls. Nearby, a large swimming pool overlooks a pasture dotted with sheep. The guest apartments, converted from peasant barracks, feature exposed bricks and crossbeams, private terraces, antique brass beds and modern kitchens. Individual rooms range from $59 to $86 a night, while a six-person apartment costs $1,076 to $1,921 a week, depending on the season. For more information, check lupinari.com or call 011-39-055-992533.
Just three miles south is another fine resort, Villa La Selva, situated on land held until the 15th century by the famed Medici family. Owner Sergio Carpini, 71, spends every spare moment hunting for antique furniture and fine Italian marble and textiles with which to furnish his guest rooms. Carpini is putting the final touches on a hilltop villa that sleeps 20. Initial restorations uncovered a Madonna and the wooden bearings of a house from the early 16th century. "Like the masterpieces in the museums," says Carpini, "this is our patrimony that must be preserved." Here too are some 200 acres of vineyards, olive groves and small lakes. Mountain bikes are available gratis. Nearby, there are also horse stables, a polo field and a championship golf course. For information, call 011-39-055-998203.
The museums and cathedrals of Siena, Arezzo and Florence are only about a 40-minute drive from Villa La Selva and Tenuta di Lupinari. A walk through the wine cellars at La Selva can be supplemented with wine tours throughout the Chianti region. Other samplings of Italian taste are nearby, including shops in Leccio that offer discounts on Gucci and Armani. The restaurants at Tenuta di Lupinari and Villa La Selva are highly regarded, as are others in the area. L'Enoteca Bengodi in Castelnuovo Berardenga specializes in homemade pappardelle pasta in rabbit sauce. Located in the central piazza, the place has a country atmosphere and exposed wooden beams. If you're in the mood for lamb-filled ravioli with cream sauce, go to Le Antiche Sere in Ambra, which is housed in a restored 15th century stone building. Buon appetito!