Enlarge Photo

Nearby Hotels: Il Salviatino, Relais La Suvera, Castello del Nero, Borgo Finocchieto, Castel Monastero, Borgo Santo Pietro

DAY 1 – Fiesole, Medici Villa, Vinci & Shopping

MORNING

Begin your tour of Tuscany in the scenic hilltop commune of Fiesole, located just five miles above Florence. Wear comfortable shoes, since you’ll be walking up and down some serious gradients. Start at the Bandini Museum to peruse its collection of terra-cotta by the Della Robbia brothers. Then head to the Badia di Fiesole, a Gothic church built in 1028 on the site of an ancient acropolis—rumored to be where St. Romulus was martyred—to view sculptures by local artist Mino da Fiesole, for whom the town’s main piazza is named. Afterward walk down Via dei Partigiani to the town’s Archeological Park, which contains a 1st-century B.C. Roman amphitheater that hosts concerts in the summer. If you’re feeling particularly energetic, grab one of the park’s tourist maps and go on one of the three panoramic walks. The shortest runs along Via Belvedere and the town’s original Etruscan walls, offering photoworthy views and an optional stop at the tranquil Convento di San Francesco.

Indagare Tip: Fiesole holds an antiques fair the second Sunday of every month. Don’t leave without sampling the gelato at Il Tucano (8R Via Gramsci).

LUNCH

Visit the esteemed Villa San Michele for an expensive yet unforgettable meal. Its spectacular views over Florence and undeniable elegance merit the praise they receive. If you prefer something more casual, check out the local favorite Vinandro (Piazza Mino, 39-55-5-9121), a small bar with outdoor tables right off the main square.

AFTERNOON

Hop in the car and head towards Vinci, the hometown of the famed Renaissance genius Leonardo, about an hour’s drive from Florence. Along the way, stop in the small town of Poggio a Caiano to visit arguably the most beautiful of the Medici villas, commissioned by Lorenzo de’Medici and finished in 1520. Originally the Medici summer residence and later home to various nobles, including Napoléon’s sister Elisa Buonaparte Baciocchi and King Victor Emmanuel II, the villa contains works by Andrea del Sarto, Filippino Lippi, Pontormo and Alessandro Allori. Enjoy the garden’s shady lanes dotted with terra-cotta sculptures and the small Italian garden with potted lemon trees. Entrance is free. Continue on 30 minutes to Vinci, to visit the fascinating Leonardo da Vinci Museum. housed in the 12th-century Castle of the Counts Guidi. Seeing Leonardo’s drawings, models and inventions in this historic context makes them seem even more significant. The small farmhouse where the artist was born is just down the road. If luxury Italian brands like Tod’s, Valentino, Gucci, Pucci, Ferragamo and Loro Piana are your weakness, search for bargains at the Mall in Leccio, an easy forty-minute drive from Fiesole on the Autostrada.

Indagare Tip: The Leonardo Museum in Vinci is great for kids, particularly followed by a tour of the site in Fiesole where Leonardo launched his famous flying machine.

DINNER

For a no-frills meal in Vinci, try Ristorante Leonardo, a cozy, rustic spot right in town. Don’t be put off by the pizzeria signage. The warm service and simple pasta dishes are reliable. For something new, and for the prestige of being among the first to try it, return to Fiesole and the recently refurbished Il Salviatino, on the hill toward Maiano. The terrace restaurant features an outdoor open kitchen and a chic alfresco lounge with white-leather couches that provide a expansive view over the city, including a direct shot of Brunelleschi’s famous dome. The more formal Le Serre restaurant occupies a greenhouse overlooking the gardens.

DAY 2 – Chianti Region

MORNING

Take the Raccordo Autostradale Siena-Firenze from Florence into Tuscany’s acclaimed Chianti region, exiting at San CascianoVal di Pesa, the highest of the northern towns, for some exceptional views. From there take the SP22 to Viale Chigiana, to glimpse Chianti’s signature hills, cypresses and vineyards from your car. Follow signs for Greve in Chianti, the first of five regional towns and site of annual shows of flowers in May and of wine in September. Continue (unless it’s Sunday, market day) to the beautiful Etruscan fortress village Castellina in Chianti. There you can check out Etruscan tombs, walk the arched Via delle Volte, an ancient, underground passageway along the city’s original walls, and visit the 16th-century neo-Romanesque Church of San Salvatore. Don’t miss Antica Gelateria, nestled in an old building with vaulted ceilings, clearly marked from the road.

Indagare Tip: If you fancy Tuscan terra-cotta, get off the Raccordo Autostradale earlier, at Impruneta, source of terra-cotta pottery and tiles, including those that adorn Brunelleschi’s dome in Florence. Choose a studio to visit beforehand, since there is no central location. A good list is can be found at www.fabbricaimpruneta.com.

LUNCH

Back on the Via Chiantigiana, head toward Gaiole in Chianti, where you can stop for a delicious lunch and wine tasting at the elegantly preserved Badia a Coltibuono. Housed in an 11th-century monastery, this organic agrotourism destination is rumored to be the birthplace of high Chianti. Reserve ahead for a table outside on the vine-wreathed terrace, and order the tasting menu, which offers handmade pasta with four pairings. Ask for a glass of the award-winning dessert wine Vin Santo and take it with you as you stroll through the impressive gardens.

Indagare Tip: If you like pottery, stop in Radda in Chianti and visit Giuseppe Rampini’s famous Ceramiche Rampini (Casa Beretone di Vistarenni) for truly exceptional customized and hand-painted ceramics.

AFTERNOON

Depending on your mood, you can spend the afternoon shopping, horseback riding, indulging in a spa treatment or tasting more wine.

Shopping: Continue east from Gaiole on the Via Chiantigiana. The road leads to Montevarchi and the Prada outlet (a must-stop for those who prize Miuccia’s designs). Follow the directions for Space Outlet, and don’t be misled by the unpromising exteriors: inside you can get up to 70 percent off retail prices.

Sport: If you’re an equestrian, drive south to Castelnuovo Berardenga and the Berardenga Riding Center (www.chiantiriding.it), run by Sadio and Donatella. Guides fluent in English lead experienced riders on two-hour afternoon rides in the Chianti countryside.

Spa: For an afternoon of spa treatments, head to Castelnuovo Berardenga and Castel Monastero’s brand–new full-range Benessere complex, which boasts with three outdoor freshwater pools, two indoor pools (including one that is saline) and an infinity pool providing cold- and hot-water experiences, including a Kneipp path, whose cold-water pebbles are said to improve circulation.

Wine: If you came to Chianti to sample its greatest asset, then head back toward Castellina in Chianti, to the small town of Vagliagli, and book a tasting at the Dievole vineyards, among the best organized and professional in the region, complete with palate cleansers of such local snacks as cured cinta senese meats and local cheeses. Indagare Tip: If you prefer a full meal with your wine, reserve the Wine Experience at the neighboring hotel, Villa Dievole, which features an extensive tasting and a tour through the cellars with the author Dario Castagno, who provides historic background on Chianti Classico, and a vintner who explains the technical side. After this, dinner is served in the cellar of the hotel’s charming Tavolo dei Maestri di Vigna restaurant.

DINNER

For guaranteed gourmet fare, try Gordon Ramsay’s latest Tuscan foray, Contrada, on the ground floor of the 11th-century Castel Monastero. With the Tuscan-themed menu, Ramsay is clearly gunning for a Michelin star; the staff’s crisp alertness feels somewhat odd in rural Italy, but the expertise of the sommelier in pairing the food with fine wines is welcome. Try the ravioli di vitello in mushroom consommé and the hazelnut-mousse terrine with pistachio gelato.

DAY 3 – Siena & Crete Senesi region

MORNING

Siena is a city of massive medieval walls and a gleaming redbrick center. Begin at the Duomo, strikingly ornate with its massive black and white tower. Don’t miss the famous Piccolomini Library, with its frescoes by Pinturicchio of scenes from the life of Pope Pius II. Next visit the thousand-year-old Santa Maria della Scala Hospital and its beautiful frescoed Santissima Annunziata Church. From Piazza del Duomo, head to the Museum of Opera Metropolitana, which contains masterpieces by Giovanni Pisano and Duccio di Buoninsegna’s fabled Maesta’ altarpiece, one of Siena’s most cherished treasures. Finally, stroll along the busy shopping streets, particularly Via di Città, where you can admire the jewels and crystal displayed in the tiny antiques store Antichità Monna Agnese (No. 45; 39-57-728-2288) .

Indagare Tip: If you’re fascinated by the city’s annual Palio horse race (held twice a year, on July 2 and August 16), arrive three days early, so you can see the trial runs, when tickets for the council bench seats are available. For the Palio itself, you have to stand for several hours, often in searing temperatures.

LUNCH

To sample traditional country Tuscan fare alongside native Sienese in a rustic setting, try Il Ghibellino (Via dei Pellegrini; 39-57-728-8079). The service may be a bit rushed and impersonal, but the food is authentic, and the prices are fair. As an alternative, bypass the tourists at the Michelin-recommended Antica Trattoria Papei for the local favorite La Taverna di San Giuseppe (Via Giovanni Duprè), to the right off Piazza del Campo,. Save room for dessert at Pasticceria Nannini (22–24 Via Banchi di Sopra), Siena’s oldest pastry shop, for espresso and a piece of chocolate panforte or roccicola (softer biscotti-like treats, in sweet almond or chocolate flavors). If it’s gelato you’re craving, skip the spots near the Piazza del Campo and head to Gelateria Nannini (affiliated with the Pasticerria), following signs for the Porta Oliva.

AFTERNOON

After lunch explore the remarkable Crete Senesi, a 300-square-mile area south of Siena whose winding country roads afford breathtaking vistas of hills and woodland. It is best known for its ocher soil, made popular by Renaissance painters, as well as its Cinta Senese pigs, whose meat is a world-renowned delicacy. Head south to Asciano, which is surrounded by a 14th-century wall. The Museum of Sacred Art houses Ambrogio Lorenzetti’s painting St. Michael Slaying the Dragon. Follow the signs to the Abbey of Monte Olivieto (Abbazia di Monte Olivieto), said to be the most beautiful in Tuscany (open only from 3:15 P.M. to 5:45 P.M). With its frescoes depicting the life of Saint Benedict and its Renaissance arcaded library, the monastery is well worth the stop, as is its tiny gift shop, stocked with the monks’ own herbal tinctures and handmade soaps.

Continue south through the Ombrone Valley along the “crater route” to the quiet town of San Giovanni d’Asso, the self-declared truffle capital of Italy. It boasts the country’s highest concentration of registered white-truffle hunters and even has a tiny museum tucked inside the castle dedicated to the delicacy. Market days are the first Monday of every month. The next large town, Buonconvento, is a wonderful conclusion to a tour of Val d’Ombrone. Stroll the cobbled streets, and visit Le Dolcezze di Nanni (36 Via Roma), whose gourmet treats are stocked at Harrods.

Indagare Tip: If you’re curious about how olive oil is made, spend an afternoon at the gleaming Fattoria Casamora (www.casamora.it), in Pian di Scó, just north of Montevarchi. This modern farm is run by Maurizio Montani, the current architect to the Vatican, and produces one of the region’s finest extra virgin olive oils. Book a lecture from the effervescent Maurizio plus a tour, complete with tastings (and lunch. if you like).

DINNER

Back in Siena, head to Ristorante da Mario (Via Soccini; 39-60-57-780-6157), in Buonconvento, to sample one of the best bistecca fiorentinas in the area. If Mario is full, try the new Le Vecchie Mura (Via Piandornella 15; 39-577-940-270), a bit smaller but with good local fare plus nice grilled fish. For something more formal, reserve a table at Il Mestolo (81 Via Fiorentina), located outside Siena’s walls but well worth the journey for delectable seafood, a rarity in these parts.

Driving Times:

• Florence to Fiesole: 20 min.
• Fiesole to Vinci: 1 hour
• Florence to Chianti: 50 min.
• Florence to Montevarchi (Prada Outlet): 45 min.
• Florence to Siena: 1 hour 15 minutes
• Siena to Asciano: 40 minutes