This list of hotels, restaurants and shops covers the area from just north of Florence to Siena and Chiusi.
Villa San Michele A luxurious hotel in a fifteenth-century monastery that overlooks Florence from the hills of Fiesole. The spectacular views make it worth a visit for lunch or a glass of wine on the terrace at sunset (4 Via Doccia, Fiesole; 011-39-055-567-82-00; doubles from $850).
Da Delfina In the village of Artimino just west of Florence, chef Carlo Cioni produces the traditional Tuscan cuisine of his mother, Delfina. (You might find her by the entrance before lunch shucking fava beans.) The terrace overlooks a bend in the Arno, and the food is deeply regional, including a deliciously dense ribollita, the classic Tuscan soup of leftover minestrone and bread. The wine list includes many of the best reds from nearby Carmignano (1 Via della Chiesa, Artimino; 011-39-055-871-81-19).
Biscottificio Antonio Mattei A handsome old bakery in Prato that makes incredible biscotti. Also try another traditional Tuscan sweet, brutti ma buoni: crunchy, light cookies made with egg whites, sugar and (usually) hazelnuts, whose lumpy shape explains the name"ugly but good" (2022 Via Ricasoli, Prato; 011-39-0574-257-56 or www.antoniomattei.it).
Castello di Volpaia A combination winery, olive mill, cooking school and bed-and-breakfast just north of Radda in Chianti. Make reservations well in advance for the cooking school and B&B; none are necessary for the winery or olive mill. During the olive harvest, from mid-November until Christmas, visitors can watch the big millstone olive presses at work and buy fresh oil to take home. Note: You have to bring a jug; you can find five- and ten-liter screw-top plastic ones at almost any hardware or housewares store (Loc. Volpaia, Radda in Chianti; 011-39-0577-73-80-66).
Da Antonio Its location, in the small town of Castelnuovo Berardenga, far from any coastline, may seem odd for a seafood restaurant. Yet this is one of the best in Tuscany, with impeccably fresh fish brought in daily, which Antonio Farina, the owner and chef, prepares exquisitely. The white wine selection is excellent, with a focus on relatively little-known Tuscan bottles (30 Via del Chianti, Castelnuovo Berardenga; 011-39-0577-35-53-21).
Il Falconiere An elegant family estate, nestled in the olive terraces below the ancient walls of Cortona, just 30 minutes from Arezzo. Owners Silvia and Riccardo Baracchi restored the place, transforming it into a Relais & Châteaux hotel (with a spectacular tower suite). The restaurant has a menu that's more international than Tuscan and offers impeccable service (Loc. San Martino; 011-39-0575-61-26-79 or www.ilfalconiere.com; doubles from $240).
Molesini A tiny yet well-stocked wine shop whose very helpful owner, Marco Molesini, is fluent in English. Try the vin santo from the nearby Avignonesi vineyards; it's widely reputed to be one of the finest in Tuscany (3 Piazza della Repubblica; 011-39-0575-63-06-66).
Montepulciano to Chiusi
Locanda dell'Amorosa This lovely hotel and restaurant was created out of a fourteenth-century fortified farmstead. The inn is in the manor house; the restaurant lies under the stables' broad stone arches. Chef Francesco Sabbadini produces a menu featuring local ingredients like the renowned Chianina beef and a heritage pork called cinta senese (Loc. Amorosa, Sinalunga; 011-39-0577-67-72-11 or www.amorosa.it; doubles from $225).
La Chiusa An inn in the village of Montefollonico, just off the road between Montepulciano and Pienza, with 15 simple but elegantly furnished rooms in what was once a family farm and olive mill. Its renowned restaurant, under the direction of chef and owner Dania Masotti, serves silken fresh pasta that's sauced with seasonal vegetables and locally made ricotta or wild porcini mushrooms from the slopes of nearby Monte Amiata (88 Via della Madonnina, Montefollonico; 011-39-0577-66-96-68 or www.ristorantelachiusa.it; doubles from $200).
La Grotta A restaurant just outside Montepulciano on the long cypress-lined avenue that leads to the magnificent domed Renaissance church of San Biagio. Specialties include homemade pastasthick strands of pici, a local specialty often served with a rich duck ragùand white truffles, in season in November and December. The first-rate wine list includes many local bottles (Loc. San Biagio, Montepulciano; 011-39-0578-75-76-07).
La Frateria di Padre Eligio A retreat with an unusual restaurant outside Cetona, near Chiusi. The place was established by a Franciscan friar to help troubled youths and drug users. The staff is composed entirely of these young people, and the talented chef, Walter Tripodi, himself a recovered addict, uses products raised on the grounds of this restored monastery (Convento di San Francesco, Cetona; 011-39-0578-23-80-15).
La Cornucopia Pienza is full of shops selling artisanal food products, but the best by far is La Cornucopia, with its wide selection of wines, pastas, olive oils and locally made Pecorino cheeses (2 Piazza Martiri della Libertà, Pienza; 011-39-0578-74-81-50; www.emporiofattorie.com).
Silvana Cugusi A cheese factory that's a great place to buy ingredients to bring home. The Pecorino cheeses are almost all made from pasteurized milk, and many are aged for months. The delicious ricotta and raviggiolo, a barely curded cheese eaten by the spoonful with a dribble of honey, are for sampling on the spot (Strada Statale 146, Montepulciano; 011-39-0578-75-75-58).
Osteria del Vecchio Castello
Susanna Fumi and Alfredo Sibaldi's Michelin-starred restaurant has recently moved to a deconsecrated Romanesque church in the Castello Banfi Brunello vineyards in Montalcino. Much of Fumi's renowned cuisine is based on research into recipes like peposo, a peppery Chianina beef stew said to have been eaten by the tile setters working with Brunelleschi in Florence (Loc. Pieve di San Sigismondo, Montalcino; 011-39-0577-81-60-26).
Osteria Le Logge A restaurant just off the Piazza del Campo with a main dining room that's lined with glass-fronted bookcases and long windows that open onto the street. Le Logge is not only cozy, it also has an elegant menu: A stuffed boned rabbit is the epitome of Tuscan cuisine, robust yet refined, while the mozzarella-filled ravioli are deliciously distinctive. Owners Gianni and Laura Brunelli produce their own wine, a Brunello di Montalcino, and the restaurant's olive oil (33 Via del Porrione; 011-39-0577-480-13). The couple has also recently opened a wine bar, Liberamente Osteria, right on the piazza, serving wines by the glass and excellent snacks (27 Piazza del Campo; 011-39-0577-27-47-33).
Antica Drogheria Manganelli A drogheria is an old-fashioned spice shop, but this one, also near the Piazza del Campo, sells all sorts of artisanal food productsfrom farro and dried beans to traditional Sienese sweets such as almond-paste ricciarelli (71 Via di Città; 011-39-0577-28-00-02).
Enoteca Italiana The government-operated national wine center in the vaulted cellars of the Fortezza Medicea displays almost every high-quality bottle made in Italy. Visitors can sample hundreds and purchase bottles to take home (Fortezza Medicea; 011-39-0577-288-497 or www.enoteca-italiana.it).