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First stop for wine lovers is the Castello di Verrazzano ((tel) 055-854-243 or 055-290-684; www.verrazzano.com), the 12th-century seat of the Verrazzano family; it’s only about 20km (12 miles) south of Florence, just outside the village of Gretti (well sign-posted). Young Giovanni Verrazzano, born here in 1485, left Chianti for adventure and discovered New York. The estate has been making wine at least since 1170, and you can sample it daily at the roadside shop; tasting is free. Their “jewel” is a 100 percent sangiovese called Sasello, while the Bottiglia Particolare (Particular [Special] Bottle) is in the Super Tuscan style, at 70 percent sangiovese and 30 percent cabernet. Tours of the gardens and cellars run Monday through Friday; book ahead at least 1 day in advance, a week or more in high season.

Greve in Chianti, about 30km (18 miles) south of Florence, is the center of the wine trade and the unofficial capital of Chianti. The central Piazza Matteotti is a rough triangle furnished with a statue of Verrazzano and surrounded by a mismatched patchwork arcade—each merchant had to build the stretch in front of his own shop. Greve is the host of Chianti’s annual September wine fair, and there are, naturally, dozens of wine shops in town. The best is the Enoteca del Chianti Classico, Piazzetta Santa Croce 8 ((tel) 055-853-297). At Piazza Matteotti 69–71 is one of Italy’s most famous butchers, Macelleria Falorni ((tel) 055-854-363; www.falorni.it), established in 1700 and still containing a cornucopia of hanging prosciutti and dozens of other cured meats, along with a decent wine selection. It’s open daily.

Greve was the birthplace of another explorer, Amerigo Vespucci (1452–1512), whose family seat is in tiny Montefioralle, on a hillside about 2km (1 mile) west of town. Educated in Florence, Vespucci went to work for the Medicis, who sent him to Spain to investigate their shipping interests. Vespucci was drawn into the world of navigation and was on the voyage in which navigators defined the coast of the South American continent, to which Vespucci lent his first name. Another famous Vespucci was Simonetta, wife of Amerigo’s brother Mario and considered to be the greatest beauty of her age. It’s often been said that the artist Botticelli used Simonetta, who died of tuberculosis at the young age of 21, as his model for Venus and his other great beauties; at his request, the artist is buried at her feet in the Vespucci church of Ognissanti in Florence.

One kilometer ([bf]2/3 mile) west of (and almost as high above) Greve perches the solid stone 14th-century medieval hamlet of Castello di Montefioralle, where the circular main street and enticing alleyways have only a few electric cables to remind you that you're still in the 21st century.

A winding, often rough road continues for several miles then drops into a lush valley where the isolated Badia a Passignano is set amid a cypress grove atop vineyards and olive groves. (As bad as this stretch of road is, 800 years ago it was once part of the "strada senese del Sambuco,” the main route between Florence and Siena.) The fortified monastery, with corner defensive towers, was established by St. Giovanni Gualberto, a Florentine who became a Benedictine monk early in the 11th century after witnessing a miracle: Setting out to avenge the murder of a relative, he took mercy when his victim laid himself before him with arms outstretched in the form of a cross. Gualberto stopped afterward to pray before a crucifix, and the Christ figure bowed his head. He soon became a Benedictine monk, but yearning for a more perfect life, he founded the Vallombrosan order here in 1049 (the name is Latin for Vallis Umbrosa or Umbrosa Valley). Gualberto died at the monastery in 1073 and is buried in the small Romanesque church of San Michele. From here you can tour a few other parts of the monastery, including the refectory where Domenico Ghirlandaio, teacher of Michelangelo, and his younger brother Davide painted a fresco of the Last Supper in 1476. A shop selling the monastery’s wine is open most days but usually it’s possible to visit the refectory only on Sunday afternoon at 3pm ((tel) 055-8071622).

South of Greve, the SS222 takes you past the left turn for Lamole. Along that road you’ll find Villa Vignamaggio ((tel) 055-854-661; www.vignamaggio.com), a russet-orange villa surrounded by cypress and elegant gardens where Lisa Gherardini, who grew up to pose for Leonardo da Vinci’s “Mona Lisa,” was born in 1479. The estate’s wine was famous in the past and in 1404 became the first red wine of these hills to be referred to as “chianti” in written record. Book ahead at least a week in advance and you can tour the cellar and ornate gardens and sample the wines.

The Chiantigiana next cuts through the town of Panzano in Chianti, 10km (6 miles) south of Greve, known for its embroidery and for another famed butcher, Antica Macelleria Cecchini, Via XX Luglio 11 ((tel) 055-852-020). Dario Cecchini loves to entertain visitors with classical music and tastes of his products, while he recites the entirety of Dante’s “Inferno” from memory. (Dario is fast becoming one of the most famous butchers in the world.)

From Castellina in Chianti, just a few mile down the road, a turn east brings you to Radda in Chianti, another important wine center that retains its medieval street plan and a bit of its walls. The center of town is the 15th-century Palazzo del Podestà, studded with the mayoral coats of arms of past podestà; among the 51 coats of arms you can make out that of the Medici, with its telltale balls. (These emblems, which might be no more poetic than representations of the cupping balls the family used in their humble origins as mere doctors, have been the brunt of jokesd since the clan’s heyday; one contemporary of Cosimo II quipped that the Medicis were determined to show off their balls even in monks’ privies.) The local butcher here is a true artisan; Porciatti will give you a taste of traditional salami and cheeses at their alimentari on Piazza IV Novembre 1 at the gate into town ((tel) 0577-738-055; www.casaporciatti.it).

Seven kilometers (4[bf]1/3 miles) north of Radda on a secondary road is the Castello di Volpaia ★★ ((tel) 0577-738-066; www.volpaia.com), a Florentine holding buffeted by Sienese attacks and sieges from the 10th to 16th centuries. The still-impressive central keep is all that remains, but it’s surrounded by an evocative 13th-century borgo (village) containing the Renaissance La Commenda church. You can tour the winery daily; the tour includes a tasting of the wines and their fantastic olive oil. The central tower has an enoteca for drop-in tastings and sales, plus award-winning (and scrumptious) olive oils and farm-produced white and red vinegars.

Some of the most beautiful scenery in Chianti surrounds the little village of Gaiole in Chianti, just to the east of Radda, where vineyard-carpeted hillsides are crowned with castles and churches. The Castello di Brolio, just north of Gaiole, is one of the most important and scenic strongholds in Chianti. For a time in the 12th century the castle was Florence’s southernmost holding, a show of might menacingly close to rival Siena; it was said that, “When Brolio growls, all of Siena trembles.” From the lovely Renaissance gardens, Siena appears like a mirage in the distance across a broad sweep of undulating southern Chianti countryside. The castle is best known these days as the domain of the Ricasoli family, who’ve been in residence for the past 10 centuries. An especially formidable member was Baron Bettino Ricasoli (1809–80), an astute statesman who served as Italy’s second prime minister and became known as the Iron Baron for his adept maneuvers in helping piece together the modern nation. Another of the baron’s long-lasting accomplishments is said to have been the invention of the recipe for Chianti, and the family continues to produce some of the region’s most esteemed labels at its Baroni Ricasoli winery ((tel) 0577–730220; www.baronericasoli.com). The family’s illustrious history and the history of the wine they introduced come to light on tours Monday, Tuesday, Wednesday, Friday, and Saturday at 10:30am and also at 3:30pm Tuesday and Friday, for 10€, and the gardens and small museum can be visited independently for 8€; the cellars and an extensive wine shop are open January to mid-March, Monday to Friday 9am to 1pm and 2 to 5:45pm; mid- to late March Monday to Friday 9am to 7pm and Saturday and Sunday 11am to 7pm; and April to mid-October Monday to Friday 9am to 7:30pm and Saturday to Sunday 11am to 7pm.

 

Top prize for most romantic spot in Chianti might go to the lovely Badia a Coltibuono ((tel) 0577-746110; www.coltibuono.com), or Abbey of the Good Harvest, about 6km (4 miles) north of Gaiole and well sign-posted. Founded in 1051, the abbey and surrounding gardens, farm fields, and vineyards were the holding of Benedictine monks until the 19th century. The gardens are a romantic concoction of hedges, beds of lavender, pools, and pergolas dripping with vines, all surrounded with magnificent cypresses and fir trees. The abbey is now the home of the Stucchi-Prinetti family, who sell their wine in their atmospheric old cellars. The estate is open to the public by guided tour (5€), mid-April to October, daily at 2, 3, 4, and 5pm.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.