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La Rignana
A long way from the main roads in Chianti wine country, the refined retreat of Cosimo Gericke and Sveva Rocco di Torrepadula has two old guesthouses. The Fattoria, enlarged in the 18th century, is based on a structure more than 1,000 years old. It contains seven rooms with rustic furnishings and sloping brick ceilings laced with wooden beams. The rooms lack TVs, telephones, and A/C, though there is a common area with a stone fireplace that has satellite television and a modem hookup. The other guest building is the two-floor Villa Stella: eight rooms with plank floors and frescoes that are available on a nightly basis only in April, May, September, and October. (At other times of year, you must rent an entire floor by the week as a single unit--four rooms, each with its own bathroom, with a common kitchen and fireplace.) The Villa is open year-round, the Fattoria from late March to mid-November. There is a horizon pool amid the olive trees, with views of the rolling hills. The restaurant, in another cluster of farm buildings and under separate management, has tables on a patio and serves traditional Tuscan fare, including wide papardelle pasta with wild boar sauce, and delectable involtini (thin veal slices wrapped around cheese and prosciutto) stewed with zucchini disks. Doubles in the Fattoria $109--$122, with breakfast; Villa doubles $154, with breakfast; four-room apartment $3,846 per week. Near Greve in Chianti, 011-39/055-852-065, rignana.it.
Podere Terreno
Roberto Melosi left a promising hotel career at London's Savoy to become chef and host of an agriturismo--an inn on a working farm in Italy. His Paris-born wife, Marie-Sylvie Haniez, who had owned a modern art gallery in Florence, decided the only proper way to run an agriturismo was to share communal dinners with their guests in the French table d'hôte style. Together, they manage a restored 16th-century farmhouse, which has seven country-comfy rooms furnished with a hodgepodge of painted metal bedsteads, carved wood vanities, and worn terra-cotta floors. Credit for the vineyard's light, organic Chianti Classico goes to Marie-Sylvie's adult son, Pier Francesco, who gave up dirt bike racing to study viticulture and enology at the University of Florence. Wine obviously means a lot to the family: Vineyards encircle the house, and each guest room is named for a local grape. Malvasia, Trebbiano, Vernaccia, and Ciliegiolo are all on the east side of the house, which has the best vineyard views. In summer, guests enjoy that same view from the patio during three-hour family-style dinners that may include lasagne, steaks, and stuffed tomatoes. Roberto and Marie-Sylvie sit at either end of the long wooden table and do their best to keep the conversation lively, in multiple languages if necessary. On cooler days, dinner moves inside to a common room, where copper pots dangle from thick wood beams and the stone walls are decorated with oil paintings, ceramics, and Marie-Sylvie's collection of sun icons. The room's seven-foot fireplace, which dates back to the 14th century, is surrounded by armchairs and a sofa that Athena (Roberto and Marie-Sylvie's miniature schnauzer) is happy to share. In the spring of 2004, Podere Terreno's simple operation got a bit swankier, inaugurating a wine-tasting cantina and a tiny spa with a Jacuzzi and massage table. Doubles $231, with breakfast and dinner. Near Radda in Chianti, 011-39/0577-738-312, podereterreno.it.
Castello Ripa d'Orcia
Once you settle into a cavernous room in this medieval castle village three miles down a curving, bumpy dirt lane, the only contact with the outside world is the pay phone in the restaurant. Accommodations are gorgeous in an antique, minimalist sort of way: very rustic, with massive ceiling beams, thrilling countryside views, and no TVs to disturb the calm--just birdsong in the mornings and the chirping of cicadas on hot summer afternoons. There's a long, narrow garden with a fountain and sunning chairs, battlements once patrolled by soldiers (now guarded by flowerpots) that make for a nice stroll, and an old granary lined with books, gaming tables, and a fireplace for guests. The owner, Countess Laura Aluffi Pentini, is part of the Piccolomini family. They're a well-known clan in these parts: Several Renaissance popes came from the family, and the Piccolominis have owned the property since 1483 (the castle itself dates back to 1218). The Countess lives in the castle, but is only guaranteed to be around during check-in time (2:30 p.m. to 6 p.m.), which adds to the feeling that, in passing through the tower gate, you've stepped out of the modern world and its frenetic pace. Doubles $147--$180, with breakfast, two-night minimum, open mid-March--October. About five miles south of San Quírico d'Orcia, 011-39/0577-897-376, castelloripadorcia.com.
Fattoria di Vagli
After two miles of dirt road winding through dense woods, a cypress-lined driveway leads to a 17th-century farmhouse surrounded by fields of corn, sunflowers, wheat, grapevines, and farro. The Vagli farm is a family operation, with Carla Ferri in charge. Her father tends the crops, her uncles shepherd the free-range pigs, cows, rabbits, ducks, chickens, and pigeons, and her mother works in the kitchen curing meats, making marmalades, and cooking for guests and the family ($23 for three courses plus dessert, without wine). Carla, meanwhile, looks after guests and the 10 rooms, furnished in a simple country style with hand-painted headboards and rough wooden beams. The rooms on the ground floor have exposed stone walls and are a bit smaller, but the abundance of light from large windows makes them feel airy. The suite with a fireplace costs $13 more, while the two units that share a bathroom cost $17 less--though those two also interconnect, so they're perfect for families. There are four free bikes for guests, and the dining room walls are lined with topographical maps to help you plan hikes and rides throughout the region--or just within the woodlands that cover most of Vagli's 800 acres. The grounds are so extensive, some guests never realize that there's a pool hidden in the fruit orchard. Once a week, a member of the family takes guests on a tour of the farming operation, which produces figs, olives, dried pork, and more. Carla also arranges guided hikes in the Castelvecchio nature reserve, which overlaps with the farm and includes the ruins of a medieval castle and village. Doubles $94, with breakfast. In Libbiano, north of San Gimignano, 011-39/0577-946-025, naturaesalute.it.
Giovanni da Verrazzano
Saturday is market day in the village of Greve in Chianti, when the main piazza is buzzing with vendors selling fruits, vegetables, porchetta (pork) sandwiches, and everyday necessities. The stalls are arranged around the statue of local sailor Giovanni da Verrazzano, the first European to discover New York Harbor. For the past 800 years, the hotel now named in this hometown hero's honor has watched over daily life on the triangular piazza. The 10 guest rooms are basic--some but not all come with a private bathroom, though modern terrazzo floors and painted metal bedsteads are standard. The location and the views are what set the hotel apart. The front rooms overlook the bustling square, while those in the back (nos. 4--7) have little private terraces with vistas over lichen-spotted roof tiles to the vast hills beyond. A larger room upstairs (no. 10), with its sloping ceilings and Persian rugs, claims similar views over the hills but no balcony. The restaurant, on a terrace atop one of the piazza's arcades, has fed hungry visitors to Greve since 1200. Doubles $127--$135, with breakfast. Piazza Giacomo Matteotti 28, 011-39/055-853-189, verrazzano.it.
Castello di Gargonza
On the crest of a mountain enveloped by forest sits a fairy-tale castle, with a 13th-century hamlet curled around the base of a crenellated tower. The hilltop village is Gargonza, fought over for centuries by the Florentines and Sienese, host to an exiled Dante in the early 1300s--and now entirely for rent. Gargonza's 27 houses, which like the castle are built of pale stone, serve as apartments and come with working fireplaces, kitchenettes, and 17th-century-style furnishings. There are also seven simple doubles (no kitchens or fireplaces) in one of the larger buildings. Converting the place into lodging for tourists was the only way Count Roberto Guicciardini--whose ancestors have been lords of the castle since 1700--could save the decaying village after the last of its farmers and artisans abandoned Gargonza in the 1960s. The central courtyard, with an old well and geraniums spilling from arcaded balconies, is a sort of open-air living room for guests. Likewise, the old olive press building functions these days as a common room with sofas, TV, and the breakfast buffet. Just outside the town's medieval walls is a swimming pool surrounded by fragrant rosemary and olive and cypress trees, and the excellent restaurant. Owner Neri Guicciardini, one of the count's sons, adds innovative flair to Tuscan classics. Doubles $130--$141 in B&B; $147--$232 in apartments. Off the SS73 west of Monte San Savino, 011-39/0575-847-021, gargonza.it.