Driving Tours

On the Road in the Florentine Chianti: En Route to Greve

Cross Florence's eastern Ponte San Niccolò and follow the signs from Piazza Ferrucci on the other side toward Grassina and the SS222 Chiantigiana. At Ponte a Ema, take a 1km ( 2/3-mile) detour to the left to the Oratorio di Santa Caterina dell'Antella, which has a wall fresco cycle of the Life of St. Catherine (1390) by Spinello Aretino. The apse frescoes are also of St. Catherine and were painted by the "Master of Barberino" around 1360.

Continuing on to Grassina, you'll find a side road leading 9km (5 1/2 miles) to terra-cotta-producing Impruneta (tourist info: tel. 055-231-3729). The Collegiata church on the main piazza was restored to its Renaissance appearance after World War II bomb damage. On the right aisle are some good baroque works -- Martyrdom of St. Lawrence by Cristofano Allori, Birth of the Virgin by Il Passignano, and a Giambologna bronze Crucifix in the chapel. The most revered bits are kept in a pair of chapels designed by Michelozzo and decorated with excellent glazed terra cottas by Luca della Robbia. Another byroad swings back onto the Chiantigiana at Santa Caterina. South on the SS222 takes you through Strada in Chianti, where a Donatello-school crucifix rests in the church of San Cristofano.

At the bend in the road called Le Bolle is a right turnoff for Vicchiomaggio (tel. 055-854-079; fax 055-853-911; www.vicchiomaggio.it). This A.D. 957 Lombard fortress was modified in the 15th century and is today one of the best preserved of the typical Chianti castles. Its estate, under British ownership, produces well-regarded wines, including Ripa delle More, a sangiovese/cabernet sauvignon whose 1997 vintage won "three glasses" from Gambero Rosso (the Italian oenological equivalent of two Michelin stars). You can taste for free at the roadside Cantinetta San Jacopo wine shop (on the SS222 right at the turnoff for the castle) daily from 9am to 12:30pm and 2:30 to 6:30pm (as late as 7:30pm in summer). Sadly, visits to the cellars, parts of which date to the 10th century, are now limited only to groups, though it's worth the short drive up here just to look at the castle exterior and for the countryside views. They do, however, offer cooking courses (anywhere from 1-2 hr. to several days) and rent rooms.

A bit farther along on the right is the turnoff for the Castello di Verrazzano (tel. 055-854-243 or 055-290-684; fax 055-854-241; www.verrazzano.com), the 12th-century seat of the Verrazzano family. Young Giovanni Verrazzano, born here in 1485, became restless with viticultural life and sailed out of the Chianti to discover New York. The estate has been making wine at least since 1170, and you can sample it Monday through Friday from 8am to 6pm. Their 100% sangiovese is called Sasello, while the "Bottiglia Particolare" ("Particular Bottle") is 70% sangiovese and 30% cab. Tours of the gardens and cellars run Monday through Friday starting at 11am (lasting until 3pm); book ahead at least a day in advance, a week or more in advance in high season (May and June especially). The cost is 10€ ($13) for a tour and tasting of three wines, and 32€ ($42) if you take the light lunch as well (you'll get a few more wines, too). On weekends, you can buy the wine at the small stand on SS222 (tel. 055-853-211).

Greve in Chianti -- Throughout the Dark Ages and Middle Ages, the Chianti castles and their heavily fortified princelings ruled the patchwork of fiefdoms that made up this area. As alliances sweetened castle-to-castle relations in the later Middle Ages, trade began flowing. Valley crossroads became market towns, and one such town began growing along the tiny river Greve in the 13th or 14th century. As trade became increasingly important, so did that market town. Today, as Greve in Chianti, the oversize village is the center of the wine trade and the unofficial capital of Chianti.

The central Piazza Matteotti is a rough triangle surrounded by a mismatched patchwork arcade -- each merchant had to build the stretch in front of his own shop. The statue in the center is of the intrepid explorer Giovanni Verrazzano (for whom the bridge in New York is named), and the narrow end of the piazza spills into the tiny Piazzetta Santa Croce, whose pretty little church houses an Annunciation by Bicci di Lorenzo and a 13th-century triptych.

Greve is the host of Chianti's annual September wine fair, and there are, naturally, dozens of wine shops in town. Some of the better ones are the Bottega del Chianti Classico, Via Cesare Battisti 2-4 (tel. 055-853-631), and 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 hundreds of other cured meats, along with a decent wine selection.

Near Greve -- One kilometer ( 2/3 mile) east 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 you're still in the 21st century. Don't miss the prettily isolated 10th-century Pieve di San Cresci, located outside the walls.

The road beyond Montefioralle continues over several miles of winding, often potholed dirt roads to the Badia a Passignano (tel. 055-807-1622), dramatically situated amid a cypress grove atop its vineyards and olive groves. The monastery was established in 1049 by Benedictine St. Giovanni Gualberto, who founded the Vallombrosan order. Gualberto died here in 1073 and is buried in what was originally the small Romanesque church of San Michele. The church is the meeting spot for tours of the rest of the monastery that leave Sundays around 3pm. The tour's highlight is the Ghirlandaio brothers' (Davide and Domenico) fresco of the Last Supper (1476) in the refectory, though it's hard to ignore the attraction of the kitchen with its massive fireplace and dozens upon dozens of Bundt cake pans nailed to the walls. The Antinori family now runs the small burg and has created a very refined osteria (tel. 055-807-1278) out of the monks' old wine cellars.

South of Greve, the SS222 takes you past the left turn for Villa Vignamaggio (tel. 055-854-661; fax 055-854-4468; www.vignamaggio.com), a russet-orange villa surrounded by cypress and elegant gardens that might seem suspiciously similar to Signor Leonato's home in the 1993 movie Much Ado About Nothing. Kenneth Branagh's choice of movie sets wasn't the first time this 14th- or 15th-century villa garnered fame: Lisa Gherardini, who grew up to pose for Leonardo da Vinci's Mona Lisa, was born here 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. Long derelict in reputation, Vignamaggio wines have been stunningly revived by the new owners, who have made it one of the top vineyards in the region. Book ahead at least 1 week in advance and you can tour the cellar and ornate gardens Tuesdays and Thursdays and sample five wines with simple snacks for 35€ ($46). They also rent rooms.

The Chiantigiana next cuts through the town of Panzano in Chianti; the tourist office is InfoChianti, Via Chiantigiana 6 (tel. 055-852-933; www.infochianti.com; Tues-Fri 10am-1pm and 3-7pm, Sat 10am-12:30pm and 3:30-7:30pm, Sun 10am-1pm). The town is known for its embroidery and for another famed butcher, Antica Macelleria Cecchini, Via XX Luglio 11 (tel. 055-852-020), where 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. (Something of a local character, Dario has been featured on more than one TV program in Italy; he held a large, well-publicized mock funeral for the bistecca fiorentina on the day it was temporarily outlawed in 2001 during Europe's mad cow disease outbreaks.)

Just south of town is the turnoff for the Romanesque Pieve di San Leolino. Beyond the 16th-century portico, this simple church conserves several 14th- and 15th-century Sienese altarpieces, including on the left aisle a Madonna with Sts. Peter and Paul (1260-80), attributed to Meliore di Jacopo, and a pretty little brick-columned courtyard off the right aisle. The SS222 continues south toward Castellina in Chianti.

A Vino Break -- The Enoteca Baldi, Piazza Bucciarelli 25, on the main traffic triangle at the Chiantigiana (tel. 055-852-843), is an excellent wine shop-cum-tasting spot offering snacks, a dart board, and good vintages of Chianti Classico, vin santo, and other Tuscan wines, grappe, and olive oils.

On the Road in the Sienese Chianti: En Route to Radda in Chianti

An Etruscan center later fortified by the Florentines as an outpost against rival Siena, Castellina in Chianti is one of the more medieval-feeling hill towns of the region and a triumvirate member of the old Lega del Chianti. The closest thing to a tourist office is the Colline Verdi travel agency, Via della Rocca 12 (tel./fax 0577-740-620). Castellina's medieval walls survive almost intact, and the central piazza is dominated by the imposing crenellated Rocca fortress. The nearby Via delle Volte is an evocative tunnel street with open windows facing out to the valley below -- it's a soldiers' walk from the town's days as a Florentine bastion. You can taste a few drops of vino at La Castellina's enoteca and shipping point in the ground floor of the family palazzo at Via Ferrucio 26 (tel. 0577-740-454). The Bottega del Vino, Via della Rocca 13 (tel. 0577-741-110; www.enobottega.it), is a good wine shop.

Outside town on the road to Radda is a 6th-century-B.C. Etruscan tomb, the Ipogeo Etrusco di Montecalvario. It's a perfect example of its type, a little green beanie of a hill surrounded by pines, topped with a pair of cypress, and slashed with stone-walled tunnels leading to the burial chambers beneath. Push the button on the little fuse box-looking thing on your right as you enter the gate to flip the lights on inside.

From Castellina, you can take a long but rewarding detour on the road to Poggibonsi into the Val d'Elsa to visit the vineyards of Monsanto (tel. 055-805-9000), which produces my favorite chianti wine. (Their Classico Riserva 1995 is about the best I've ever tasted.) At this medieval estate, Dr. Laura Bianchi carries on her father Fabrizio's often iconoclastic oenological traditions -- after buying Monsanto in 1961, he was among the first to produce a 100% sangiovese chianti, and using only sangiovese grosso grapes at that. (Because this was illegal back in 1974, they still listed all the unused grapes on the labels.) Aside from their exquisite "chardonnay" (aged half in steel and half in wood, so that its fruitiness isn't overpowered with oak but still has its body and longevity), they use native grapes as much as possible. The result is a suite of remarkable and singular wines, like Il Poggio, a full-bodied elixir made with 90% sangiovese and 10% Colorino and Canaiolo (aged in Slovenian-wood barriques), or Tinscvil, a sangiovese-cabernet Supertuscan whose name, in Etruscan, means "Gift to the gods." They started bottling that last one after discovering an Etruscan tomb on the property, which also inspired them to extend their vast cellars with a huge hall built using a low Etruscan-style arch. Down here and in the original 18th-century cellars are stored thousands of bottles from every year of production -- many still for sale. They do tastings and direct sales Monday through Friday from 8:30am to 12:30pm and 1:30 to 6pm; reserve a tour of the cellars for 16€ ($21) per person at least a few days in advance.

If you're tired of these wine-sodden hills, you can shoot down the Chiantigiana from here to Siena, an 18km (11-mile) trip. It takes you past the medieval village of Fonterutoli (tel. 0577-740-212; www.fonterutoli.com) -- a working borgo that has been supporting the winemaking business of the Mazzei Marquis since 1435. Fonterutoli produces some of the most highly regarded wines in the region, including an excellent Chianti Classico and Chianti Classico Riserva, Supertuscans Siepi and Brancaia (the latter a sangiovese and merlot cru), the rich berry-flavored Belguardo (a Morellino di Scansano cru), and the superb fruity I.G.T. Badiola, a sangiovese wine (with 3% each of merlot and cabernet) meant to be drunk young, after about 2 years. The direct sales office in town is usually locked; follow the signs for the ristorante to find the easygoing, old-fashioned bar where you can sample their bounty (and get the barrista to fetch a few cases from that direct sales office when you're ready to buy). You can taste and buy daily from 10am to 10:30pm. While you're there, be sure to buy a bottle or two of Fonterutoli's olive oil, which is also superb.

The road continues on to Siena, passing through Quercegrossa, the birthplace of Siena's great sculptor Jacopo della Quercia. But if you want to explore what many consider the best of the Chianti, it's time to cut east into the rugged, mountainous heart of the old Lega del Chianti along the SS429 toward Radda.

Just before you hit Radda, a signposted right turn will take you a winding 7km (4 1/3 miles) past the Romanesque San Giusto to the Castello di Ama, a top-rated winery whose Frenchified methods are seen by some as bucking homegrown tradition -- they not only produce a merlot vino di tavola but also age almost all their more traditional Tuscan wines in -- gasp -- French oak barriques. The quality of their oakey chianti can't be disputed, however, and they also produce an excellent barrel-aged pinot grigio along with silky olive oils. Direct sales (year-round) and tastings (Easter-Sept) are available down the road in the hamlet of Lecchi at the Rinaldi Palmira shop (tel. 0577-746-021) on Via San Martino 8. (If there's no one inside, ask at their little grocery store next door.)

Radda in Chianti & Environs -- Radda in Chianti], one of the three players in the original Lega del Chianti and still an important wine center, 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; it contains the tourist office (tel./fax 0577-738-494; www.chiantinet.it; Mon-Sat 10am-1pm and 3-7pm, Sun 10am-1pm; in winter, mornings only). The local butcher here is a true artisan; Luciano Porciatti and his sister 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). They also sell local products, from wines to pasta, at their enoteca along Radda's tunnel-like old soldier's wall walk.

Seven kilometers (4 1/3 miles) north of Radda on a secondary road is the Castello di Volpaia (tel. 0577-738-066; fax 0577-738-619; www.volpaia.com), a first-rank wine estate with a medieval stone heart. The castle here was 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. Sunday through Friday, you can tour the winery -- installed in a series of buildings throughout the little village (with an eye to preserving its medieval visual charm, there is nonetheless high-tech plumbing, through which the wine flows, buried seamlessly inside the stone walls) -- for 11€ to 23€ ($14-$30) per person depending on the size of the group (cheaper for larger groups); the tour includes tasting of the wines and their fantastic olive oil. Call ahead, preferably a week in advance. The central tower has an enoteca (open 10am-6pm; closed Feb) for drop-in tastings and direct sales of some of the wines that helped found the Chianti Consorzio in 1924, plus award-winning (and scrumptious) olive oils and the only farm-produced vinegars in the Chianti. They also rent apartments and two small villas and lease out a small hotel on a neighboring hill of the estate.

Three kilometers (2 miles) east of Radda, get on the left byroad for a 19km (12-mile) trip to the beautifully isolated Badia a Coltibuono (tel. 0577-749-498 or 0577-74-481; fax 0577-749-235; www.coltibuono.com). The abbey's core was founded in A.D. 770, but the monastery was owned and expanded by the Vallombrosan Order from the 12th century to 1810, when the Napoleonic suppressions passed it into private hands and it became an agricultural estate. You can visit the 11th-century San Lorenzo church only during daily Mass (open 4:30pm in summer, 3:30pm in fall, 3pm in winter, and 4pm in spring). Today, the estate is owned by the Stucci-Prinetti family, which oversees the wine production; try their Sangiovetto label, a 100% sangiovese wine. The family's most famous member, international cookbook maven Lorenza de' Medici, started a famed (and egregiously overpriced) culinary school here in summers, though it's now run by an acolyte, and her son, Paolo, runs the fine and oft-acclaimed on-site restaurant (tel. 0577-749-424; closed Mon and Nov-Feb). There's a direct-sales office for their products called the osteria (tel. 0577-749-479) down at the main road. March through December, the osteria is open Tuesday through Saturday from 9:30am to 1pm and 2 to 6:30pm, and Mondays from 2 to 6:30pm.

En Route to Sienna

Follow the scenic road leading south out of Radda toward Siena along the valley of the Piana stream and you'll immediately see the 17th-century Villa Strozzi-Sonnino crowning a steep hillside of Vistarenni vines to your left (tel. 0577-738-476; www.villavistarenni.com). They offer direct sales weekdays from 8:30am to 5:30pm and will set up tastings for small groups (book at least a day in advance) as well as tours of 18th-century cellars. Like most vineyards these days, they also offer apartments and villas for long-term rental; visit the website for details and photos.

A bit farther south on this road, on the left side, you'll see the ceramic workshop and showroom of master Giuseppe Rampini (tel. 0577-738-043). Here the Gubbio-born maestro (who still remembers gathering clay from the Tiber riverbed for his father when he was 8) and his assistants create hand-painted ceramics based on antique Florentine motifs or inspired by the Renaissance art of Venetian painter Archiboldo. The front space is full of pattern displays; the back room has individual pieces for sale.

Heading south directly from Badia a Coltibuono on the SS408 will take you through Gaiole in Chianti, the third member of the Lega del Chianti. The tourist office is at Via Ricasoli 50 (tel. 0577-749-411; gaiole@chiantinet.it; open Mon-Sat 9:30am-1pm and 3-6:30pm). An ancient market town like Greve, Gaiole is now basically modernized without much to see, aside from the wine shops: the Cantina Enoteca Montagnani, Via B. Bandinelli 13-17 (tel. 0577-749-517), and La Cantinetta del Chianti, Via F. Ferruci 20 (tel. 0577-749-125).

A side road here leads west past the 12th-century Castello di Spaltenna (now a hotel) 3km (2 miles) to the 13th-century Castello di Vertine, an imposing castle surrounded by a 9th-century village.

East of Gaiole, an unfinished road winds up to the fortified medieval hamlet of Barbischio. For more castle viewing, head south of Gaiole to the turnoff for Meleto and Castagnoli. Castello di Meleto's twin circular towers stand mighty at either expanse of a long blank wall to watch over the estate's vineyards. The poor castle-cum-villa was built in the 1100s, partially dismantled by the Sienese in the 15th century, rebuilt by the Florentines, and then smashed by the Sienese again in the 16th century before a 1700s restoration transformed it to the villa we see today. Farther up this road is the hamlet of Castagnoli, wrapped around the thick, squat walls of an early medieval castle.

Farther south of Gaiole, the SS484 branches east toward Castelnuovo Berardenga and the famous Castello di Brolio (tel. 0577-749-066; www.ricasoli.it; pull the bell rope and wait). The Chianti as a region may date to the 1200s, but Chianti Classico as a wine was born here in the mid-19th century. The Brolio castle has been in the Ricasoli family since 1141, though its vineyards date from at least 1007; the current fortress was rebuilt in 1484. "Iron Baron" Bettino Ricasoli inherited it in 1829 at age 20 and, before he went off in 1848 to help found a unified Italy and become its second prime minister, spent his days here, teaching -- really dictating -- scientific farming methods to his peasants. He also whiled away the time tinkering with grape varietals. By the mid-19th century, he'd arrived at a quaffable formula balancing sangiovese, canaiolo, trebbiano, and malvasia grapes that was used when Italy's wine-governing DOC and DOCG laws were written in the 1960s. You can visit the castle grounds, including the small chapel (Bettino rests in peace in the family crypt) and the gardens, and walk along the wall for a good view of the lower Chianti valleys. Admission is 3€ ($3.90). In summer, the gardens are open daily 9am to noon and 3 to 6pm; in winter, from 9am to noon and 2 to 5pm.

After years of being passed from larger to larger corporate ownership, Brolio declined as a winery; then in 1993 the Baron Francesco Ricasoli bought it from Seagram's and brought it back into the family. He effected a drastic turnaround, investing billions of lire, replanting vines, and rigorously revising the philosophy to rocket Brolio back to superstardom and respect on the Italian wine scene, winning acclaim and awards once again. They now produce several wines, including the newest -- a single Castello di Brolio, 100% sangiovese Chianti Classico. They're going for the French châteaux concept, where the wine is associated with a place, not a brand. To buy their award-winning wines, visit the wine shop (tel. 0577-749-301) from Monday to Friday between 9am and 7:30pm, Saturday and Sunday from 11am to 6:30pm. They offer cantina tours by appointment (call at least a few days in advance) with a wine tasting at the end, for 21€ ($27) per person for up to five people (11€/$14 per person if the group is larger). On the side of the private road up to the castello is also a quite good Osteria del Castello restaurant (tel. 0577-747-277).

The westerly byroad out of here leads most quickly to join the SS408 as it heads south, out of the land of the black rooster and into Siena.