I felt a little sheepish going to Tuscany...again. But it's where I wanted to be. Anyway, no one, no matter how well traveled, admonishes, "Oh, forget Tuscany, it's so over." This time, I was in search of rural retreats I could pretend to call home—family-run places, often converted from estates or farms. I wanted something a step below a villa, a rung above a casa—in other words, in Italian words, a hotel borgo. Hard as many of them were to find, all the U-turns paid off. In Tuscany, the rougher the road, the softer the bed at the end of it.

Relais Il Falconiere

I'll admit the name gave me pause. Here I was, seeking out authentic Italian places and bumping straightaway into a hybrid. Many travelers, I know, rely on the Relais & Châteaux group (of which Il Falconiere is a relatively new member) as the source for exclusive places to stay. But in this case, the word relais, with its fine French associations, was a red flag; I feared mutton dressed as lamb.

I was wrong. In the care of Silvia and Riccardo Baracchi, the family estate has flowered. A hedge of clipped boxwood leads to an upright villa, once the residence of poet Antonio Guadagnoli, now a hotel with 12 guest rooms, including a tower aerie whose panoramic view compensates for its compact size. Tucked behind another hedge, this one of rosemary, is the pool, where maids in pink were laying out stacks of yellow towels. Beyond an apricot tree, two suites fashioned out of former barns flank the family chapel, the doors to which are opened in the evening.

The grounds are well tended without being too formal; service is attentive, never brusque. It's at the restaurant, occupying the limonaia (a greenhouse where lemon trees were wintered) and its adjacent covered terrace, that a French veneer emerges. The menu is elaborate, the tableware refined, the waitstaff more mannered than usual for Italy. This all seemed fine to me—but not the piped-in music and the far-too-cold light from mercury-vapor lamps. Then the power went out, leaving us diners to sense more than see our dinners. Where once the scent of lemon drifted, now the air was perfumed by black olives and thyme, honey and fennel. In the dark, Italy prevailed.
Relais Il Falconiere, 370 LocalitÀ San Martino, Cortona; 39-0575/612-679, fax 39-0575/612-927; doubles from $212, including breakfast.

Hotel Borgo Pretale

Arriving at Borgo Pretale, buried deep in the woods, I passed half a dozen mountain bikes sheltered by a thatched awning, and then an equal number of bows (the sporting kind) next to a bag of golf clubs by the front door. The hotel's main structure dates to the 13th century—its magnificent tower is even older—but the temporary life lived here by guests is of the active late-20th-century sort. Unlike many of the places I visited, where the favored activities are sipping coffee or Campari, sleeping late, and retiring early, 35-room Borgo Pretale energizes guests by virtue of the "on-campus" offerings. Carved into its 50-acre oak, chestnut, and laurel forest are tennis courts, a pool, a putting green and driving range, an archery field, a bocce court, and six miles of bike trails. This is an ideal hotel for the museum-weary-and for kids.

The ground-floor rooms of the restored farm buildings are popular with families. Young StairMaster couples claim the tower. Rooms here exhibit just the right degree of rustic elegance: plain white walls, heavy dark beams, bedspreads and canopies done up in a noble stripe. Ceilings are high, the windows smallish (the inoperable slit in my bathroom began life as a loophole, a slot for arrow-aiming). At the top of the tower, in place of what could have been a honeymoon suite, is an open-to-all living room with a fireplace and windows on three sides: a democratic gesture that signals the management's thoughtfulness.

The front-desk staff keeps busy providing suggestions for guests in search of local wine and olive oil, and, for me, the right point of entry into walled Siena, 15 miles away. Though I was headed for a meal at a friend's house, it was comforting to know I could have done as well staying in. The prix fixe dinner menu serves up three choices per course: everything from funghi del bosco, translated on the menu as "mushrooms with wood flavor," to "stuffed rabbit Etruscan-style." Breakfast offered a wide selection, too, though its presentation—folding buffet table, plastic packets of jelly—seemed less in the Italian style. What was unmistakably Tuscan was the light filtering through a live oak, the jasmine climbing the tower, the bees cozying up to wild roses. But for the murmur of contented guests, all was quiet.
Hotel Borgo Pretale, Rosia; 39-0577/345-401, fax 39-0577/345-625; doubles from $205. (Along with a confirmation, Borgo Pretale faxes guests directions. Consider them as necessary to remember as your passport.)

Il Borghetto
San Casciano Val di Pesa

Il Borghetto does have a sign, a stone tablet hardly bigger than a large tissue box, so tastefully set into a tall hedge that I assumed it marked a private residence. Only after the third pass did I notice the engraved lettering and the electronic gate buzzer. Everything about Il Borghetto, even its name (which means "little village"), is secretive yet welcoming. I wound my way around a handsomely restored 15th-century building, stepped into the house through a not-so-obvious front door, and meandered from dining room to sitting room. It was the siesta hour but within minutes a trim, smiling woman appeared, knowing exactly who I was. Impressive, I thought, until I discovered that the other six rooms had been booked by participants in a small cooking program that the hotel hopes to continue next year. The proprietors had saved me the suite at the top, with two of everything: two bedrooms, two bathrooms-too much room, really, though somehow still cozy. Best of all was an oval window that swung open above the pedestal sink, admitting sound effects (a tractor and a couple of late-to-work roosters) to match the rural view.

It's hard to believe that Florence is only a half-hour to the north. Even so, the countryside around Il Borghetto holds more than the usual agricultural interest. Down the road is the estate of the Antinoris, one of Italy's best-known wine families and among the largest landholders in Tuscany. Immediately to the south I came across an Etruscan tomb, only to discover later that I need look no farther than my own back yard, with its terraced gardens and orchard, for another, this one belonging to an archer. Following Il Borghetto's mowed path through an olive grove and happening upon the tomb was transporting—I imagined the people who lent Tuscany its name clambering over these very hills with their bows and arrows, let's see, just 25 centuries earlier?

Breakfast was simple and luscious: coffee, crusty rolls, homemade jams. But the hotel serves no other meals, so at dinnertime I went in search of La Cantinetta di Rignana, a country restaurant even more tucked away than Il Borghetto, and equally worth the trouble of finding. My steak, grilled over a wood fire, was perfection. I returned to Il Borghetto via gravel roads, for once regretting that I knew the way.
Il Borghetto, San Casciano Val di Pesa; 39-055/824-4442, fax 39-055/824-4247; doubles from $220. La Cantinetta di Rignana, two miles southeast of Badia a Passignano; 39-055/852-601; dinner for two $55; closed Tuesdays.

Monticchiello di Pienza

A few years back, I thought I had landed at the ideal Tuscan retreat: a small hotel sequestered in a 15th-century monastery set in an architectural jewel, the Renaissance village of Pienza. Then came the catch-22 of all perfect places: the hotel (Il Chiostro di Pienza) drew more visitors to the town, expanded to accommodate them, and became big enough to book small tour groups. Pope Pius II's birthplace is still magnificent (it's best known to Americans as the location for Zeffirelli's Romeo and Juliet), his Palazzo Piccolomini a must, but once the buses arrived, I'm afraid I had to be going.

I didn't have to go far. Down the hill from town, I found L'Olmo, a 17th-century country house and a smaller companion building, with five suites in all, flanking a courtyard. With its high walls, handsome wrought-iron furniture, and overflowing pots of flowers, the courtyard is the ideal outdoor living room.

Unlike northern Tuscany, much of which is forested, the area around Pienza is gloriously open—a landscape of giant picnic blankets laid edge to edge, capturing every shade of green and every contour of the earth. Wheat fields, their rhythmic wave setting a relaxed and hypnotic pace, rise around L'Olmo, though the hotel itself sits on a plateau high enough for every room to have a spectacular view. From the pool, I could see all the way west to Amaita Mountain. To the east lie the thermal waters of Chianciano Terme, the noble wine town of Montepulciano, and, closest of all, the nearly unknown village of Monticchiello.

Italian friends had circled Monticchiello on my map and recommended a detour, especially if I was coming in late July or early August when the tiny settlement becomes a stage, its residents cast members in a townwide production. All was quiet in June, but for the churr-churr-churr of an espresso machine and the miao of a lazy cat, about the only living thing to be spied within the walled stone village. At its edge, two cafés provide the staples—coffee, wine, olive oil, bread, gossip. After the bustle of Pienza, Monticchiello is the perfect place to downshift and linger over a prosciutto-mozzarella-and-tomato-with-a-grind-of-pepper sandwich before returning to the hotel for a swim and a doze.

L'Olmo guests have the option of a bed-and-breakfast or half-board plan (lunch isn't served). Take the latter, especially if you're staying just a few days. Owner Francesca Lindo not only manages the hotel, but she runs the kitchen, ensuring a dedication to your dinner. Her menus draw from recipes tipiche del territorio, meaning the chances are good for handmade pasta with a tomato sauce, or rabbit with olives. The best advantage of eating where you sleep, or, rather, of sleeping where you eat: getting a little loose with the Montepulciano and grappa, which in turn makes the crickets chirpier, the stars that much more brilliant.
L'Olmo, Monticchiello di Pienza; 39-0578/755-133, fax 39-0578/755-124; suites from $190.

And keep in mind...
Hotel Belvedere di San Leonino Castellina in Chianti; 39-0577/740-887, fax 39-0577/740-924; doubles $100, including breakfast; dinner for two $45. With its country setting and easy access to the motorway, this 28-room hotel in tiny San Leonino is an ideal base for exploring the Chianti region and Siena, eight miles south.
Locanda Le Piazze Castellina in Chianti; 39-0577/743-190, fax 39-0577/743-191; doubles $165, including breakfast; dinner for two $66. For every stone the Bonini family reset while shoring up this 20-room farm, off a gravel road eight miles west of Castellina in Chianti, they planted a flower or vine, meaning that guests are as intoxicated as the bees and butterflies. The Boninis also added a pool and restaurant.
L'Ultimo Mulino La Ripresa di Vistarenni, Gaiole in Chianti; 39-0577/738-520, fax 39-0577/738-659; doubles $181, including breakfast; dinner for two $70. This riverside medieval mill has 13 guest rooms, a pool, restaurant, bar, and well-stocked wine cellar.