Divine art, delicious food, decadent hotels, Dionysian wines, and a handful of essential books to help you enter into the spirit of Italy's most seductive region

Tuscany is one of the largest and most varied of Italy's regions, encompassing Renaissance Florence and medieval Siena, as well as a vibrant coast, a host of small hill towns, and famous vineyards. The months of September, October, May, and June are the most beautiful and also the best time to sample local produce such as truffles and porcini (in fall), and zucchini flowers and fava beans (in spring). During the peak months of July and August, huge numbers of travelers are vying to get into the same museums, hotels, and restaurants. To help plan your time, consider booking a trip through Insider's Italy—Marjorie Shaw lives in Rome and tailors itineraries for foodies, oenophiles, architecture buffs, and families (insidersitaly.com).

The country code for Italy is 39. All prices quoted are for September 2008.

FLORENCE AND CHIANTI

Florence has an unparalleled concentration of Renaissance art and architecture—including icons such as the Duomo, the Uffizi, and the Pitti Palace—all within an easily navigated city center. Hence the tourist crush. Book tickets to galleries and museums in advance through your hotel concierge or travel agent. Nearby Chianti was one of the first wine areas to make Tuscan red a household staple and has since become a favorite of British expats.

After a seven-year renovation, the Four Seasons Florence reopened this summer. The grand property joins two palazzi in one of the city's largest gardens (055-26261; doubles, $788–$1,261). In the Piazza di Santa Maria Novella, J. K. Place has a modern design (055-264-5181; doubles, $552–$788). Residence Hilda, a two-minute walk from the Duomo, has spacious rooms and competitive prices (055-288021; doubles, $300–$552). The Ferragamo group owns a number of fashionable properties, including the Gallery Hotel Art and the Lungarno Suites (055-272-640-00; doubles, $542–$700; suites, $700–$908). Across from the Piazza Santissima Annuziata, the Loggiato dei Serviti, in a palazzo built by Antonio da Sangallo the Elder, has large, pleasant rooms at modest rates (055-289-592; doubles, $240–$327). The intimate Casa Howard Florence feels like the home of a well-connected local, but services are scant (06-699-24-555; doubles, $252–$394).

If you prefer to stay a little out of town, the Villa Mangiacane has wonderful views of Florence, plus three pools, a spa, a vineyard, and some Michelangelo frescoes (055-829-0123; doubles, $478–$638). The painstakingly restored 16th-century Villa Bordoni, near Greve, has a good restaurant (055-884-0004; doubles, $366–$494; prix fixe, $72).

In Pisa, the Relais dell'Orologio is a remodeled ancient tower five minutes from the Duomo and across the street from the house where Leopardi wrote his famous verses about Silvia. The lovely if pricey inn also has an excellent restaurant (050-830-361; doubles, $556–$638; prix fixe, $70).

Florence is still one of Italy's top dining cities; avoid the tourist traps and stick to simple trattorias where you'll find better, and cheaper, food. Since 1869, locals have flocked to Sostanza-Troia for its excellent bistecca alla fiorentina and unpretentious, bustling atmosphere (25r Via del Porcellana; 055-212-691; entrées, $25–$32). Settle onto the long benches at Alla Vecchia Bettola and follow your waiter's recommendations on the daily specials (34r Viale Luigi Ariosto; 055-224-158; entrées, $16–$24). The city's most famous chef, Fabbio Picchi, has a formidable empire of restaurants, where he delivers modern takes on Tuscan classics: Cibrèo (8r Via Andrea del Verrocchio; 055-234-1100; entrées, $40–$50), Trattoria Cibrèo (122r Via dei Macci; 055-234-1100; entrées, $15–$20), Cibrèo Caffè (122r Via dei Macci; 055-234-5853; entrées, $7–$12), and Teatro della Sale (111r Via dei Macci; 055-200-1492; buffet, $40, plus a onetime $8 membership fee).

SIENA AND SOUTHERN TUSCANY

Siena is a mecca for medieval buffs, with most of the action concentrated around the huge Campo. Nearby Montalcino, Pienza, Montepulciano, and Cortona are exquisite hill towns with lovely countrysides and vineyards. South of Montepulciano, the gardens of La Foce, established by Iris Origo in the 1920s, are historically interesting and gorgeous. The estate has a few lovely houses available for short stays. It recently opened the Villa La Foce for weekly rentals—a 15th-century three-story former tavern with period furnishings that can sleep 21 people (057-869-101; lafoce.com; $30,777 per week).

Most of Siena's best hotels actually fall outside its wall. Borgo Santo Pietro, 35 minutes to the southwest, near the spectacular Abbey of San Galgano, is a renovated 13th-century villa with 6 bedrooms (soon to be 12), landscaped gardens, a boccie court, a pool, and orchards (0577-75-1222; doubles, $528–$781). Within the walled city of Cortona, San Michele is an imposing 16th-century palazzo with comfortable rooms at reasonable rates (0575-604-348; doubles, $350–$398). Near Pienza, the contemporary-styled La Bandita, which has views of the Val d'Orcia, is an 8-room inn (also available for weekly rental) owned by Condé Nast Traveler contributing editor Ondine Cohane's husband (333-404-6704; doubles, $470–$598). In the center of Montepulciano, La Locanda di San Francesco has a few well-priced rooms with views, plus a wine bar with local vino nobiles and Montalcino's brunellos (0973-664-384; doubles, $112).

Montepulciano's Acquacheta is owned by a zany Tuscan who likes his steak rare and won't cook yours any other way. The place is so popular that he often has to take three seatings a night (22 Via del Teatro; 0578-758-443; entrées, $20–$47).

Luciano, the owner of Pienza's Sette di Vino, has a similarly impassioned approach, warning tourists as they walk in that there is "no pizza, no pasta, no Diet Coke." At lunch he serves lighter dishes such as grilled meats, pecorino sampling platters, and salads (1 Piazza di Spagna; 0578-749-092; entrées, $7–$8). Latte di Luna, also in Pienza, has an outdoor terrace and local dishes such as pici al cinghiale, or wild boar, and maialino, or suckling pig (2/4 Via San Carlo; 0578-748-606; entrées, $9–$20). Il Rossellino, the fanciest (and tiniest) joint in town, is run by a husband-and-wife team (4 Piazza di Spagna; 0578-749-064; entrées, $27–$32).

In the small town of Monticchiello, famous for its Teatro Povera, La Porta's highlights include taglioni al tartufo, tagliata, and the owner, Daria Cappelli, who knows her wines (1 Via del Paino; 0578-755-163; entrées, $18–$29). In a former pharmacy right off Siena's Campo, the well-known Le Logge is still one of the city's best restaurants (33 Via del Porrione; 0577-480-13; entrées, $25–$27). Most people don't think of eating fish in Tuscany, but Tre Christi reminds visitors that they are just 45 minutes from the Mediterranean. Try the excellent crudo (17 Vicolo di Provenzano; 0577-280-608; entrées, $22–$28).

VINEYARDS

The best way to explore Tuscan vineyards is by sampling vintages. In Montepulciano, Avignonesi has one of the best vino nobile blends (0578- 724-304; avignonesi.it). In Chianti, the wine trail is well marked; stop by San Giusto a Rentennano (0577-747-121; fattoriasangiusto.it) or Isole e Olena (055-807-2767). Brunellos are Italy's superstars; visit the medieval fortress in Montalcino for a brunello overview—after walking up the ramparts for marvelous views—and then head to Castello di Argiano for a taste of Sesti brunello, an authentic version of the sangiovese grape (39-348-912-5660; by appointment only). Casanova di Neri is an example of a more modern take on the wine (0577-834-455; casanovadineri.com), and Ciacci Piccolomini d'Aragona is one of the oldest and most established producers (0577-835-616; ciaccipiccolomini.com).

Reading

The classic modern Tuscan novelist is Aldo Palazzeschi, whose Materassi Sisters tells the story of two spinsters who grow besotted with their unusually handsome (and unscrupulous) nephew (out-of-print). Vasco Pratolini, a left-wing, working-class Florentine novelist who also wrote screenplays for Luchino Visconti, left a number of affecting novels, most notably The Naked Streets, a coming-of-age story set in a poor quarter of Florence (out-of-print). War in Val d'Orcia, Iris Origo's dispassionate World War II diary, culminates in her marching orphans to safety through Tuscany (David R. Godine, $15). Eve Borsook's Mural Painters of Tuscany: From Cimabue to Andrea del Sarto is the best guide to the Tuscan art of the fresco (out-of-print); also recommended is her Companion Guide to Florence (out-of-print). Italian speakers will want Aria di Siena by the great Cesare Brandi (Progaton, $15).
–Dan Hofstadter, Ondine Cohane