Stretching between Florence and Siena in the heart of Tuscany, the Chianti wine region is the romanticized Italy of daydreams: terra-cotta-roofed towns, wine-soaked dinners and vineyards stitching sun-dappled hillsides. But hidden amid Chianti’s winding roads and rolling hills are some surprisingly modern attractions. There’s made-to-measure fashion, new standout architecture, and contemporary art worth a detour. Certainly, there are copious amounts of red wine waiting to be drunk, but don’t expect kitschy straw-wrapped bottles or pizza-parlor reds. Today Chianti vintners are producing excellent, nuanced wines that are worthy of these scenic surroundings.



3:30 p.m.
1. Wine Structure

The Antinori clan has been producing wine in the region since the 1300s, but the family company, Marchesi Antinori, is now planting for the future. In the fall of 2012, a new, architecturally stunning winemaking facility called Antinori nel Chianti Classico was inaugurated. And in March, the glass-and-rusted-steel complex opened to the public for tours of its elegant cantina and grounds. The hourlong tour (20 euros, or $26 at $1.31 to the euro; by reservation) begins on an elevated walkway under the cantina’s sloping terra-cotta-tiled ceiling and concludes in a glass-enclosed tasting room. There’s also a small museum of artworks and wine artifacts, including an ancient wooden wine press whose design is linked to Leonardo da Vinci.

6 p.m.
2. Pretty in Panzano

A hilltop village may be an unlikely location for stylish fashion, but at the leather-specialty shop Verso x Verso, in the small town of Panzano in Chianti, that’s exactly what you’ll find. Even more surprising is that all the beautiful clothing and accessories on display can be made to order. So would you prefer a rounded or square toe on that handmade pair of caramel-hued oxfords? Or would you like to be fitted for a bespoke jacket — the double-zippered style in orange goat suede is gorgeous — by the Florentine-trained designer herself? After placing your order, stroll down the cobblestone alleys of this medieval village and indulge in the sunset views.

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3. Dinner da Dario

Remain in Panzano to partake in the evening’s carnivorous feast at Officina della Bistecca, a restaurant owned by the eighth-generation butcher Dario Cecchini. A convivial atmosphere pervades the long communal tables onto which course after course of meat arrives in different cuts and methods of preparation, from beef tartare to grilled Panzanese steak. Fittingly for a restaurant attached to a butcher shop, even the baked potatoes are accompanied by a jar of delectable, spreadable lardo — “Chianti butter.” But the night’s climax is the bistecca alla Fiorentina, which Dario himself exuberantly announces while proudly pumping a pair of the humongous steaks above his head like a victorious prizefighter in the ring. Dinner, including wine, water and grappa, is €50; reservations recommended.


10 a.m. 
4. Around the Piazza

Greve in Chianti is the region’s principal town and the host of a long-running Saturday morning market. On Piazza Matteotti, the town’s triangular main piazza, browse the temporary market stalls that surround a permanent monument to the navigator Giovanni da Verrazzano, whose family estate is nearby. Several small artisanal shops are also tucked under the pretty porticoes that ring the piazza. Don’t miss La Bottega dell’Artigianato, filled with hand-woven baskets and cutting boards carved from the wood of olive trees, or Antica Macelleria Falorni, a gloriously scented butcher shop that has been selling local salumi in the same location since the 18th century.

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5. History Lesson

To learn about the history of Chianti’s viticulture, visit the informative Museo del Vino (admission, €5; make weekend appointments in advance), where most exhibits are underground in former wine cellars. The collection spans hand-cranked wine presses, rudimentary corking contraptions and other old tools of the trade. But most interesting is the area that delves into local lore about another world-famous explorer with supposed ties to the region: Amerigo Vespucci, after whom the Americas were named.

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6. Liquid Lunch

Descend into the sprawling cellar of Le Cantine di Greve in Chianti for a light lunch of regional products. Starting with the vino, choose among scores of wines that are dispensed from high-tech machines designed to preserve wine quality after bottles are opened. Try a Tignanello, one of the original Super-Tuscans, or compare the Chianti Classico of different vineyards by using the simple automated system: insert a card purchased at the register (from €10), press the button corresponding to the wine you want, and out pours a taste into your glass. When you find a favorite, sit down at a marble-topped table beneath brick-and-stone arches and munch on a panino stuffed with fennel-flavored salami (€3) or a platter of pecorino and prosciutto crostini (€6). Finish the meal by sampling local olive oils or grappa.

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7. Ama Art

Down a bumpy dirt road in the countryside, the rural hamlet of Castello di Ama (current population: 4) is an unexpected setting for museum-worthy contemporary art. The “town’s” handful of handsome buildings are now part of the Castello di Ama winery — one of Chianti’s finest — and house some of the works that the winery began commissioning over a decade ago. Today the collection consists of a dozen permanent pieces, including Anish Kapoor’s glowing hole in the floor of a tiny stone chapel and Kendell Geers’s crimson neon sign that reads “Revolution” (or “Love,” depending on your perspective) in a wine cellar. A two-hour guided visit of the winery (€35; book in advance) includes a tour of the artworks as well as a tasting of the estate’s fruity olive oil, pressed on-site, and the prestigious wines of the vintner Marco Pallanti.

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8. Local Dining

As the sun sets, gather for an al fresco meal at Mangiando Mangiando, a small osteria on Greve’s main piazza that sources seasonal products from nearby farms. Beneath canary-yellow canopies, dine on crostini with local goat cheese, stuffed rabbit and pastas like fresh taglierini smothered in a succulent sauce with cinta senese pork. For dessert, try the classic combination of crunchy cantuccini with sweet vin santo. Dinner for two, about €50.

11 p.m. 
9. No Red Ahead

Chianti has few worthwhile night-life options, but one exception is La Birroteca di Greve, a craft beer pub specializing in artisanal Italian brews. Outdoor tables overlook a large piazza and the town’s modern new library; inside, there is a peppy soundtrack of ’50s tunes. The pub’s eight taps, whose offerings rotate weekly, recently featured the hoppy Marruca ale from the Tuscan microbrewery Birra Amiata and the Kölsch-style Rodersch from Birrificio Bi-Du, a brewery near Como (medium-size draft beer, €5).


11 a.m. 
10. Handmade Treats

The village of Castellina in Chianti is a lovely hilltop maze of terra-cotta and stone, complete with a long vaulted passageway that tunnels through the medieval town walls. But the town is also home to L’Antica Delizia, a gelateria that is among the finest in Tuscany. At this family-run shop, choose among flavors that often include imaginative offerings like ricotta-and-pear or dark-chocolate-ginger. Then take your treat on a stroll to the nearby showroom of Lucia Volentieri, a Tuscan artist whose varied oeuvre includes iron sculptures, pastel-hued watercolors and delicate bas-relief ceramics. If the shop is open (hours vary), admire the detailed pieces up close; otherwise settle for marveling through the large windows.

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11. Buried Treasures

Prominently situated in the middle of Castellina is an impressive stone fortress with a tall crenelated tower, built for defense in the Middle Ages. Today only peaceful proceedings take place inside the structure, which houses the Archaeological Museum of Chianti Senese (admission, €5). The museum features ancient artifacts from area excavations, including many from Etruscan settlements that were first discovered over a century ago. Take a peek into the present-day work being performed in the adjoining research area and, for those who can’t get enough of all things Etruscan, get driving directions to nearby sites, such as the burial mound at Monte Calvario.

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12. Sculpted Beauty

On the half-hour drive from Castellina to the Chianti Sculpture Park, through bucolic hills draped in vineyards and olive groves, sublime views unfold around each hairpin turn. But once you arrive at the 17-acre park (admission, €7.50), the sights are best discovered on foot. Simply follow the wooded half-mile trail that winds past 20-odd sculptures in a multitude of materials and styles. Along the way, you can spiral through a life-size labyrinth made of glass cubes, and gaze under the bridge of bright blue tiles that, on clear days, frames the dreamy skyline of Siena in the distance.