A Wine Tasting Road Trip Through Tuscany’s Chianti Classico Region: panzano to radda and gaiole

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This article is the second of a two part series on a self-guided wine-tasting road trip through Tuscany’s famed Chianti Classico wine region. The first installment included the wine-destination cities of Siena, Castellina and Greve in the Chianti Classico region. This article resumes where the previous article left off - in the city of Greve-in-Chianti - and continues the wine tour by exploring the wine-destination cities of Panzano, Radda and Gaiole-in-Chianti.


Leaving Greve-in-Chianti, head south on the Via Chiantigiana (SR222), backtracking towards Panzano.

The next stop on the way to Panzano might be for lunch or dinner and/or a wine tasting at Fattoria Montagliari. This small, family-owned-and-operated winery has been producing wines for almost 200 years. In addition to several Chianti Classico wines, Fattoria Montagliari also produces some Grappa, Amaro and Vin Santo, all of which are available for sale or tasting.

Fattoria Montagliari has a trattoria on the property that does an excellent job of preparing traditional Tuscan dishes. Weather permitting, you can take your meal on the shaded terrace with its awe-inspiring view of the Greve Valley below.

V. Montagliari,29 - Panzano-in-Chianti.  Phone: +39 055-852-014. Email info@fattoriamontagliari.com
Montagliari Website

Panzano is one of the larger towns in Chianti and it long ago outgrew the limitations of its original city walls and houses and buildings today cascade down the hill below the ancient city walls. The town has a sleepy, laid-back vibe and while there is not a lot to see, it’s still worth a stop to take in the picturesque views and perhaps a longer stay if you want to visit any of the numerous and prestigious wineries in the area.

There are several wine bars on or close to Piazza Bucciarelli, the town’s main square, where you can buy or sample local wines.

The Accademia del Buon Gusto is one such wine bar. Located in the old part of town, it markets a small number of interesting wines in a pleasant, art-filled tasting and sales room.

Accademia del Buon Gusto
Piazza Ricasoli, 11 - Panzano-in-Chianti.  Phone: +39 0558-560-159. Email info@accademiadelbuongusto.com. Buon Gusto website

Panzano hosts a major wine festival on Piazza Bucciarelli during the third weekend of September. Called Vino al Vino, this festival has wines from most of the Panzano area producers as well as other Tuscan wineries available for tasting. This wine festival follows by a week the larger one held in Greve-in-Chianti. Its smaller size makes it more manageable in that it is easier to navigate, lines are shorter and it generally has a more intimate feel. The festivities usually include music and art shows as well as numerous food stands.

Local wineries that offer tours and wine tastings

Castello dei Rampolla

The Rampolla winery near Panzano dates back to the 13th century. Today the di Napoli family incorporates modern, well-equipped cellars with biodynamic methods in the vineyard to produce world-class Chianti Classico and Super-Tuscan wines.

Because of their early and innovative strategies in developing Cabernet-based Super-Tuscan wines as well as their rigorous quality standards and their adoption of biodynamic methods in the vineyards and cellars, the estate’s wines have developed an enthusiastic if not cult-like following.

Via Case Sparse, 22 - Panzano in Chianti. Open all year round 10:00 am - 1:00 pm and  2:30 - 5:00 pm. Phone: +39 0558-52001. Email castellodeirampolla.cast@tin.it. Website not yet available.


Located a short distance south of Panzano, the Fontodi winery is one of the most dynamic and acclaimed wineries in the Chianti Classico region. The wines from this environmentally-sensitive estate are certified organic.

Azienda Agricola Fontodi - Panzano-in-Chianti. Phone: +39 0558-52005. Fontodi Website

Castello di Monsanto
Castello di Monsanto lies about 10 miles west of Panzano near the hamlet of Barberino Val D'Elsa, within sight of the towers of San Gimignano to the west. Castello di Monsanto produces elegant and long-lived Chianti wines.

Via Monsanto, 8 -  Barberino Val D'Elsa. Phone: +39 0558-059-000 for tours and wine tastings. Email monsanto@castellodimonsanto.it. Monsanto Website

Panzanello is a relatively new winery located approximately midway between Greve and Panzano. It practices organic farming techniques and produces a small but interesting list of wines. Visitors have several wine tasting and/or food options available in the estate’s cozy tasting room or on the terrace with its great view of the Tuscan countryside.

Via Case Sparse, 86 - Panzano-in-Chianti. Phone: +39 0558-52470. Email: info@panzanello.it. Panzanello Website.

Where to dine with good wine in Panzano
Cantinetta Sassolini
Well prepared traditional Tuscan cuisine served in a welcoming environment.

Piazza Ricasoli, 2 - Panzano. Phone: +39 0558-560-142. Sassolini website  


Leaving Panzano, head south on SR222 a short distance and then turn left (east) onto SP2bis (Strada Provinciale di Lucarelli). Follow this scenic road a short distance, then turn left again onto SR429 and a few minutes later you arrive in Radda-in-Chianti. The trip from Panzano to Radda takes less than 20 minutes.

Originally built as a fortified town, some of Radda’s original city walls and towers are still intact. It is a small, post card-pretty town that unfortunately has far too many tourists.

radda-in-chiantiThe 15th-century Palazzo Communale is the center of the old town and the 15th-century Palazzo del Podesta is gaily festooned with various coats-of-arms on its stone walls. The nearby Chiesa di San Nicola is small but worth a visit.

But Radda is not known for its art or architecture - its primary claim to fame is as a wine destination. The town hosts a variety of wine bars and wine-centric restaurants and there are numerous, well-known wineries in the surrounding countryside.

The consortium of Chianti Classico producers recently opened the Academy of Chianti Classico, also known more formally as the Bottega del Vino Gallo Nero, in the former Convent of Santa Maria al Prato in Radda. Part of its mission is to educate consumers about Chianti Classico wines and toward this end it has an enoteca that offers a large selection of Chianti Classico wines for tasting by the glass. Its hours are from 10 am - 11:30 pm Tuesday through Sunday.

The Academy also sponsors a more formal and intensive three-hour seminar on how to taste and evaluate Chianti Classico wines that includes a review of the Chianti Classico regulations followed by a guided tasting of 3 Chianti Classico wines. For more information on this wine-tasting seminar visit the Academy Wine Website

Local wineries that offer tours and wine tastings

The Vignavecchia winery has been in the Beccari family since the 1870's. Located in the gently rolling hills a short distance from Radda, the winery produces a number of well-made red, white and rosato wines.

Localita Vignavecchia - Radda-in-Chianti. Phone: +39 0677-738-090. Vignavecchia website

Castello di Volpaia

The small, medieval hamlet of Volpaia is located just a short drive north of Radda along a picturesque road. This ancient town is the real thing. Originally built in the 11th century as a fortified village, much of the town’s original architecture is still intact and it is a joy to walk around and explore the architecture and layout of the town. It has fewer tourists and far more interesting architecture than Radda.

This state-of-the-art Castello di Volpaia winery is scattered throughout the village of Volpaia - it practically is the village. It seems like the entire village is involved in the production of the estate’s wines, olive oils and other products. The estate produces several highly-regarded Chianti, Chianti Riserva and Super-Tuscan wines. Reservations are required to tour the cellar and/or taste wines.

Castello di Volpaia also has a formal restaurant where you can dine inside or on the terrace situated on the ancient castle walls. Open from 12.00 noon to 7.00 pm. Closed on Wednesday.

Phone +39 0577-738-066. Email Bioenoteca@volpaia.com.

castello di Volpaia Website

Enoteche and Wine Shops in Radda-in-Chianti

Enoteca Casa Porciatti

This enoteca/wine store has an extensive selection of Tuscan wines available for sale by the bottle or glass.

Piazza IV Novembre, 1 - Radda-in-Chianti.  Phone: +39 0577-738-234. Casa Porciatti Website

Bar Enoteca Dante

Piazza Dante Alighieri, 1 - Radda-in-Chianti. Phone: +39 0577-738-815. Enoteca Dante Website

Enoteca Toscana
Via Roma, 4 - Radda-in-Chianti.  Phone: +39 0577-738-845. Enoteca Toscana Website

Where to dine with good wine in Radda-in-Chianti
Osteria Le Panzanella
Located just outside Radda on the road to Panzano, this small osteria has an extensive list of red, white and sparkling wines. The menu features traditional dishes that change depending upon what produce is locally available and has a pleasant, shaded terrace for dining. Closed Monday.

Località Lucarelli, 29 - Radda-in-Chianti.  Phone: +39 0577-733-511. Le Panzanella Website

Ristorante La Bottega

This highly-regarded restaurant is located on the main square in Volpaia, a short distance from Radda. It serves hand-made pasta and traditional local dishes all accompanied by a great wine list. Come in advance of your reservation and walk around this charming ancient village. Closed Tuesday.

Piazza della Torre, 1 - Radda-in-Chianti. Phone: +39 0577-735-602.

La Bottega Website

Next door to the Ristorante La Bottega is the Bar-Ucci, a wine bar/restaurant owned by a member of the Barucci family that also owns Ristorante La Bottega. Bar-Ucci serves light meals and wines in an informal setting. Closed Monday.

Piazza della Torre, 9 - Radda in Chianti. Phone: +39 0577-738-042.

Bar-Ucci Website (in Italian).


Just a few miles east of Radda-in-Chianti lies the small, wine-centric town of Gaiole-in-Chianti. Situated as it is on a relatively flat valley floor, Gaiole prospered in centuries past as an easily-accessible trading center. While Gaiole lacks some of the architectural and scenic attractions of Chianti’s hill-top towns, the town’s main attraction is its status as a major wine center. The town is packed with enoteche, wine-themed restaurants and the nearby hills are home to several of Chianti’s most acclaimed wineries.

Local wineries that offer tours and wine tastings

Castello di Brolio

The 12th century Castello di Brolio has been involved in wine production for centuries and is reputed to be oldest producing winery in Italy. It has a magnificent castle, probably the finest in Tuscany, and the castle and gardens are well worth a tour prior to a wine tasting.

There is a variety of wine tasting options available at the winery. You can book tastings at the Brolio enoteca or you can reserve a tour of the vineyards followed by a guided tasting of the estate’s wines in a private tasting room. Other tasting opportunities include a tasting of the estate’s wines accompanied by a specially-prepared luncheon at Osteria del Castello, the estate’s restaurant. 

Castello di Brolio - Gaiole-in-Chianti. Phone: +39 0577-7301. Castello di Brolio Website.

Le Capannelle
This small-production boutique winery is set in a renovated 16th century farmhouse. The simple charm of the farmhouse provides a picturesque backdrop for the sleekly modern, high-tech winemaking and cellaring facilities of the winery. Le Capannelle offers various tastings of the estate’s wines in combination with special luncheons tailored to the wines served.

Località Capannelle, 13 - Gaiole-in-Chianti. Phone +39 0577-74511. Le Capannelle website

Castello di Lucignano
Castello di Lucignano offers both cellar tours and wine tastings. A guided tour of their wine cellar can be followed by a specially-prepared lunch with wines at “Solissimo”, the estate’s on-site restaurant.

Località Lucignano, Gaiole-in-Chianti. Phone: +39 0577-747-810.

Castello di Lucignano Website

Castello di Meleto

A short distance due south of Gaiole on top a gently-rolling hill lies the imposing 13th century  Castello di Meleto. The winery offers guided tours of the castle with its old underground wine cellar and various wine tastings accompanied by cured meats and other Tuscan specialties. The estate’s restaurant “La Fornace di Meleto” offers a formal luncheon where your can also sample the estate’s wines.

Castello di Meleto - Gaiole-in-Chianti. Phone: +39 0577-749-129. Castello di Meleto Website

Castello di Ama

About 3 miles southwest of Gaiole in the tiny hamlet of Ama lies one of the Chianti’s premier wineries, Castello di Ama. The estate has developed a cult-like following for its elegant, award-winning Chianti Classico and Super-Tuscan wines. It hosts several types of wine tastings, all of which require advance reservations.

Località Ama - Gaiole in Chianti. Phone: +39 0577-746-031.


Where to dine and drink good wine in Gaiole-in-Chianti
Osteria il Papavero

Osteria il Papavero is located a few miles east of Gaiole in the tiny hamlet of Barbischio. It is a small and friendly restaurant with great food and service.  Closed  Monday.

Localita Barbischio, 15. Phone: +39 0577-749-063. Papavero Website

Ristorante Malborghetto
An excellent restaurant tucked away in the ancient, small and hard-to-find hamlet of Lecci. It serves well-prepared traditional Tuscan dishes. Closed Wednesday.

Via Monteluco, 4 - Lecchi, Gaiole-in-Chianti. Phone: +39 339-3034-871. Email malborghetto@malborghetto.net. Malborghetto Website

Le Contrade
This restaurant is ocated a short distance from Gaiole in the small town of Vinci. Perched on a rolling hill, Le Contrade enjoys magnificent views of the Chianti countryside. Friendly service, an extensive wine list and an interesting menu featuring some creative takes on traditional Tuscan dishes all combine to make this a destination restaurant.

Localita Vinci. Phone: +39 0577-749-504. Le Contrade Website

Il Celliere a Castagnoli
The restaurant is situated in the courtyard of the ancient Fortress of Castagnoli, located a few miles south of Gaiole. It serves up some exceptional Tuscan cuisine.

Localita Castagnoli, Via del Castello, 2 - Gaiole. Phone: +39 0577-731-921. Email: ilcelliere@gmail.com. Il Celliere website

Badia a Coltibuono

No tour of the Chianti Classico region would be complete without a visit to Badia a Coltibuono (or “the Abbey of Good Harvest”) located just a View of Badia a Coltibuonofew miles north of Gaiole.

A winding road leads up to the Abbey, an 11th century Romanesque monastery, and its destination restaurant. Badia a Coltibuono also has a famous cooking school founded decades ago by famous author and cookbook writer Lorenza de Medici.

The restaurant is set in a lush botanical garden on the top of a hill that offers a commanding view of the valley below. Lunch or dinner here is a memorable way to end any tour of the Chianti Classico region.

While Badia a Coltibuono has a winery that produces some engaging Chianti Classico and Super-Tuscan wines, the actual winery is located about 12 miles from the Abbey. However, the restaurant naturally serves the estate's wines and there is a wine and gift shop at the entrance to the Abbey where you can buy the estate’s wines and olive oils and some other locally-produced products.

Localita Badia a Coltibuono - Gaiole in Chianti. Phone: +39 0577-749-031 Email: ristbadia@coltibuono.com. Coltibuono Website


©Richard Marcis
October 8, 2014

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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