A Wine Tasting Road Trip Through Tuscany’s Chianti Classico Region: Siena to Castellina and Greve

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The Chianti Classico region has for centuries been one of the most popular destinations for tourists and wine enthusiasts alike.

Geographically situated in central Tuscany, the Chianti Classico zone extends from just below Florence south to the edge of Siena. This broad area is sprinkled with scenic hill-top villages, crenelated castles and ancient abbeys and the area's rolling hills are dotted with wineries surrounded by sweeping vineyards.

There are also numerous wineries as well as wine bars (enoteche in Italian) and wine shops scattered throughout the region including even the smallest villages and hamlets. Its a paradise for wine enthusiasts whether they be novices or wine savants.

The Chianti Classico area is one part of a larger geographic area generlly labeled the Chianti region. The Chianti region covers a vast area within Tuscany and is comprised of eight separate and well-defined geographic areas, each of which is permitted to affix their regional Chianti name to wine labels.

The Chianti Classico zone is the oldest and most prominent of the eight Chianti-designated areas. With its long history, strict regulatory requirements and roster of internationally-recognized wineries, the Chianti Classico region is generally regarded as the premier Chianti wine region. It produces and exports a lot of wine and is central Italy’s winemaking powerhouse.

The name Chianti Classico has become part of the popular wine jargon and is probably the wine that people first think of when Tuscan or Chianti wines are mentioned. The popular black rooster (or Gallo Nero as its known in Italian) emblem affixed to necks of Chianti Classico wine bottles serves to reinforce this subliminal association. The Consorzio Vino Chianti Classico, a consortium of Classico producers, works hard to promote Chianti Classico wines and protect the black rooster trademark.

The Chianti Classico region received DOCG status in 1995 and the regulations delineate not only where but how and when Chianti Classico wines can be made. While the regulations have been liberalized somewhat in recent years they still provide a systemic framework for production of Chianti Classico wines that has to be observed by every Chianti Classico producer.

All Chianti Classico wines must contain at least 80 percent Sangiovese. Chianti Classico wines are distinguished by their floral bouquets with distinct notes of violets, rich but not heavy textures and discernible tannins that gradually soften over time. With their good acidity they are extremely food-friendly wines that pair well with most pasta, vegetable and white meat dishes.

But Chianti Classico wines are not the only ones produced in the Chianti Classico zone. Other wines popularly referred to as “Super-Tuscans” are also produced here and some are as highly-regarded, if not more so, than Chianti Classico wines.

The Super-Tuscan designation is a term of art, an informal marketing designation unencumbered by any regulatory restrictions. Super-Tuscan producers have complete flexibility in terms of how they fashion their wines. This includes producer discretion in what grape varieties are used as well as vineyard management and cellaring techniques.

For example, while all Chianti Classico wines are Sangiovese-based, some producers may not include any Sangiovese in their Super-Tuscan wines, opting instead to include other indigenous varieties and/or “international” varieties such as Cabernet Sauvignon or Merlot.

These wines are in effect proprietary blends created to reflect individual producer’s styles and predilections.  What makes Super-Tuscan wines stand out from the crowd is not any seal of regulatory approval but the reputation and attention to quality provided by the individual producers.

Today it is hard to find a Chianti Classico producer that doesn’t include one or more Super-Tuscans in their lineup of wines. When visiting wine bars, wineries and/or restaurants in the Chianti Classico region you are sure to see some Super-Tuscans alongside Chianti Classico wines on the wine list. If you have the opportunity, taste both, compare, and savor the differences.

With this background and after reading this article's predecessor companion piece titled six Tips to Enhance Your Wine Tour of Tuscany's Chianti Classico Region, we're ready to start our Chianti Classico wine-tasting road trip.


Even though Siena lies outside the Chianti Classico zone - the Chianti Classico zone begins a few miles north of Siena - it is a good jumping-off point for a tour of the Chianti Classico region and no visit to the Chianti area would be complete without a stop in Siena. With its dazzling collection of medieval churches, palaces and towers, Siena is one of Tuscany’s most memorable cities and a major destination for tourists.

While rich with history Siena also has a vibrant, contemporary vibe as people live, work and go about their daily activities in an urban environment.

The center of urban activity is the fan-shaped Piazza dei Campo. Indelibly linked with the Palio dei Campo - the famous horse race run twice a year in the Piazza - the Piazza dei Campo is a masterpiece of medieval planning and architecture and is truly awe-inspiring. The Piazza is dominated by the sturdy but graceful Torre del Mangia. Next to it is the imposing Palazzo Pubblico which serves as the town hall but whose upper floors house the city’s museum with its numerous Sienese art treasures.

View of SienaOther must-see sites in Siena include the magnificent black and white, zebra-striped Duomo (cathedral), the Baptistry, the church of San Francesco, the Pinacoteca Nazionale, the Basilica of San Domenico, the Museo dell ‘Opera del Duomo and the 16th-century Fortezza Medicea.

While there are no vineyards or wineries in Siena, the town nonetheless has a vibrant wine scene with numerous, well-stocked wine bars and restaurants dispensing wines by the bottle and the glass from not only the Chianti Classico region but from all over Italy.

Some of the more interesting wine destinations in Siena include the following:

Enoteca Italiana
Enoteca Italiana is an institution in Siena. Located in the 16th-century Fortezza Medicea on Piazza Liberta, it is a public institution founded to promote the best Italian wines and wineries. Almost every variety of wine Italy produces is available here by the glass or by the bottle.

The Enoteca Italiana is a must for all wine lovers. It includes a wine shop, a restaurant and a wine bar where you can sample Italian wines while enjoying an exotic view of the city from the terrace. The wine bar is open daily from 3:00 pm to midnight.

Fortezza Medicea - Piazza Libertà, 1 - Siena.  Phone: +39 0577-228-843.

Enoteca I Terzi
Enoteca i Terzi is located in the Torre dell’Orsa, a renovated 12th century stone tower just a short distance from the Piazza dei Campo. This well-stocked wine bar offers a huge selection of Chianti Classico and other Italian wines. It also has a restaurant that serves typical Sienese dishes.

Torre dell’Orsa - Via dei Termini, 7 - Siena. Phone: +39 0577-44329. I Terzi Website

Compagnia dei Vinattieri
This upscale wine bar and restaurant is located just a few steps off the Campo. Great atmosphere, superb food, an amazing wine list and friendly service all combine to make it a popular place for tourists and locals alike.

Via delle Terme, 79 - Siena.  Phone: +39 0577-236-568. Vinattieri Website (italian only)

La Bottega di Dedo
La Bottega di Dedo is a cozy wine bar with a touch of Italian sophistication. The wine list highlights boutique, up-and-coming producers and labels, including a number of organic and natural wine producers. It has some quality food options to accompany the wines that make it a perfect venue for aperitifs, lunches, dinners or just tasting wines.

Via Simone Martini, 23 - Siena.  Phone: +39 3806-567-330. La Bettega di Dedo website.


When leaving Siena, head north on SR222 (otherwise known as the Chiantigiana highway) that bisects the Chianti Classico region and is one of the most scenic and enjoyable touring routes in Italy. The first major wine destination north of Siena is Castellina-in-Chianti. It is a scenic town with a lot of history and is a great introduction to the Chianti Classico region.

Perched on a hill, Castellina has fabulous views in all directions. view of castellina in chiantiEncircled by its mostly-intact ancient walls and dominated by an imposing Rocca di Castellina fortress the town has a distinctly medieval character. There are several narrow, ancient alleys that are great for strolling and taking the measure of the town. The town’s main thoroughfare is a cobblestone street lined with interesting wine shops, restaurants and stores selling local crafts and other products.

Not far from Castellina is a large Etruscan tomb dating to the 6th century BC that has been excavated and is now open to the public.

Not only is Castellina one of Chianti’s most ancient and charming hill towns it also is a wine destination town with several close-by vineyards and wineries and a variety of shops and wine bars in town that offer an extensive selection of Chianti Classico and other Tuscan wines for sale or tasting.

Local wineries that offer tours and wine tastings
Castellare di Castellina
This environmentally-sensitive winery includes a print of a different endangered bird species every year on its wine labels. Guests are welcome for tastings of the estate’s wines and/or purchase of wines.

Phone: +39 0577-742-903; Email: info@castellare.it. Castellare Website

Castello di Fonterutoli
Castello di Fonterutoli has been owned by the Mazzei family for almost 600 years and is one of Chianti Classico’s oldest and most prestigious wineries. The winery is located just a short distance outside Castellina.

Combine a tasting of estate wines and/or tour with lunch or dinner at the Fonterutoli estate's restaurant, Osteria di Fonterutoli website.

Phone: +39 0577-741-125. Email: osteria@fonterutoli.it. Fonterutoli Winery Website

Rocca delle Macie
This winery is located a few miles south of Castellina in the tiny hamlet of Fizzano. A young and dynamic winery, Rocca delle Macie has within a relatively short period established itself as one of Chianti’s finest wineries,

Phone: +39 0577-732-236. Email: info@roccadellemacie.com. Rocca Delle Macie Website

Where to dine and taste wines in Castellina-in-Chianti
Enoteca le Volte
Housed in an historic building in the center of Castellina, the Enoteca le Volte offers a variety of Chianti Classico and other Tuscan wines for purchase or tasting by the glass.

Via Ferruccio, 12 Castellina-in-Chianti Phone: +39 0577-740-308. Le Volte Website

Enoteca Bottega del Vino Cantina Orlandi
Conveniently located across the street from the tourist information office in central Castellina, this well-stocked wine shop sells and offers tastings of a variety of Tuscan wines.

Via della Rocca, 13 - Castellina in Chianti. Phone: +39 0577-741-110. Cantina Orlandi Website

Antica Trattoria La Torre
This is a popular, informal and family-run trattoria serving traditional Tuscan fare in a warm, welcoming environment.

Piazza Umberto, 1 Phone: +39 0577-740-236. Trattoria La Torre Website

Ristorante Albergaccio di Castellina
This upscale restaurant is located in an old farmhouse with a pleasant terrace for summer dining. The menu changes frequently and features modern takes on traditional Tuscan cuisine. Reservations required.

Via Fiorentina, 63 - 53011 Castellina-in-Chianti. Phone: +39 0577-741-042. Albergaccio Website

Riserva di Fizzano Ristorante
This is the Rocca Delle Macie winery’s onsite restaurant located a short distance southwest of Castellina.  You can have lunch or dinner here as part of the winery’s tasting sessions. Closed Wednesday.

Phone: +39 0577-73723.  Email: ristorante@roccadellemacie.com. Fizzano Ristorante Website

Osteria del Laghetto
Located on the road between Castellina and Monteriggioni, this osteria has an outdoor terrace with a great view for summer dining. Closed Monday. Phone: +39 0577-743-125.

L’Antico Ristorante Pestello
The restaurant is located on SS429, a few miles northwest of Castellina on the way to Poggibonsi. It has a warm atmosphere, good food and friendly service with a pleasant veranda for outside dining. Closed Wednesday.

Phone: +39 0577-740-671. Email:info@anticoristorantepestello.it. Ristorante Pestello Website. (Italian only).


Leaving Castellina, continue north on the Chiantigiana highway (SR222), you will pass by the town of Panzano - which merits a stop on our return trip - before arriving at the region's main wine town, Greve-in-Chianti. Unlike many other wine destinations in the Chianti Classico region, Greve is situated on a flat, valley floor and consequently lacks some of the picturesque charm of the many nearby hill-top towns.

The heart of this small town is Piazza Matteotti, an attractive triangular-shaped piazza where a bustling market takes place every Saturday morning. The Piazza is the focal point of the town and is lined with pottery shops, restaurants, bakeries and wine stores. Also located on the square is the imposing Palazzo del Comune which serves as Greve’s city hall.

It’s a lively and vibrant town where food and wine festivals typically accompanied by music and local produce markets occur regularly all year round but are especially popular during the summer and early fall months.

In the center of the Piazza is a statue to Giovanni da Verrazzano, a local boy with a sense of adventure who in 1524 became the first European to sail into and thus “discover” what is now New York harbor. To commemorate this feat the Verrazzano Bridge connecting Staten Island and Brooklyn is named in his honor.

Greve is the unofficial capital of the Chianti Classico region. Greve has a long wine history. The hills surrounding Greve are home to many famous wineries and Chianti’s largest wine fair is held every September in Greve.

The Greve Tourist Office, which is tucked away in a corner of Piazza Matteotti a short distance from City Hall, is a good place to get information and maps of the numerous area wineries. It is open Monday through Saturday from 10 am-12:30 pm and 4:30-7 pm.

Every second weekend of September, Greve hosts what is probably Tuscany’s greatest wine fair, the Expo of Chianti Classico Wines or, more formally, the Rassegna del Chianti Classico. Held on Piazza Matteotti in Greve, the Greve Chianti wine fair has dozens of Tuscan wineries represented, each offering a variety of Tuscan wines with Chianti Classico, of course, taking center stage. It is a crowded but fun wine festival. You buy a wine glass for about 10 euros and that entitles you to sample up to 10 wines of your choice. There is plenty of food available to accompany the wines and music, dance and art exhibitions are part of the festivities.

Less than a mile away on a small hill overlooking Greve is the small village of Montefioralle. It is a well preserved, interesting medieval fortified village and is well worth at least a short visit. It’s virtually free of automobiles and it's a pleasure to casually stroll its circular, one-and-only street.

Montefioralle's modest size belies its historic significance. In the Middle Ages it was one of the largest military and administrative complexes in all Tuscany. The intact city walls have four gates which still exist albeit in slightly modified form.

It is also the birthplace of the famous explorer Amerigo Vespucci whose early 16th-century explorations of the New World placed him in the history books when the American continents were named after him. His ancestral home still stands in Montefioralle, marked only by a very simple plaque.

Local wineries that offer tours and wine tastings
Castello di Verrazzano
There is a long tradition of winemaking at the Castello di Verrazzano with records indicating that wine was produced here as far back as the 12th century. The Castello offers an interesting mix of different types and numbers of estate wines for tasting at different price points.

Via Citille, 32A - Greti  Phone: +39 0558-542-43. Email: info@verrazzano.com. Verrazzano Website

Villa Vignamaggio
Villa Vignamaggio is a picturesque and historic property. It reputedly is the birthplace of Mona Lisa and was the setting for Kenneth Branagh’s 1993 film, “Much Ado About Nothing.”

The estate has produced wines for centuries and today offers a number of highly-rated wines that include Chianti Classico, Chianti Classico Riserva, several Super-Tuscans as well as Vinsanto and Grappa.

Villa Vignamaggio offers daily morning and afternoon tours of its gardens and wine cellars followed by guided wine tastings of a number of the estate’s premier wines. The tours and tastings are by reservation only.

Via Petriolo, 5 Greve-in-Chianti. Phone: +39 055-854-661. Email: degustazioni@vignamaggio.com. Vignamaggio Website

Where to taste good wines in Greve-in-Chianti
Le Cantine di Greve-in-Chianti
Le Cantine di Greve in Chianti is a vast commercial enoteca stocking more than 1,200 wines of which at least 140 wines are available for tasting (including Vin Santo and grappa).  The enoteca has a pay-by-the-glass automated system where you purchase a wine card, select a wine of your choice, a precise amount of wine is dispensed into your glass and the cost deducted from your card balance.

You can accompany your wine tasting with platters of choice salami, prosciutto and other cold cuts prepared in the Cantina’s renowned family-owned butcher shop.

Galleria delle Cantine, 2  Greve-in-Chianti. Phone: +39 0558-546-404 Email: info@enotecafalorni.itLe Cantina Website.

This concludes the first part of a wine-tasting road trip through Tuscany’s famed Chianti Classico region. A follow-up article resumes the Chianti Classico wine tour itinerary where this article ends and explores the enoteche, wine-friendly restaurants and wineries in and around the cities of Panzano, Radda and Gaiole-in-Chianti.


©Richard Marcis
Revised November 4, 2018

Note – Information regarding the wine bars, restaurants and wineries reviewed is accurate as of the date of this posting. However, this is Italy and closing dates and hours of operation for organizations can change with little or no notice. To avoid disappointment it is always advisable to check their websites in advance and/or make reservations by phone, fax or email where appropriate.

To view other travel itineraries in Italy, see Things to do and see in Italy



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