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Chianti wine trail from Florence to Siena in Tuscany, Italy

  • Chianti wine trail from Florence to Siena

    The Chiantigiana (SR 222) is one of the most scenic and charming motoring routes in Italy, running directly south from Florence to Sienna cutting through the heart of the Chianti Classico wine zone. The road sweeps around rolling Tuscan hills and past thousands of hectares of vineyards, all producing outstanding Chianti Classico DOCG (the highest classification of Chianti).

    The Chianti area has been one of the most important wine producing regions in Italy for over two centuries. It was the family of the Grand Duke of Tuscany Lopold I that began cultivating grapes during the 18th and 19th centuries in the region that would become modern Chianti.
    The best time of year to visit Tuscany (Toscana) is at harvest time in September, or just before harvest to see the vines bowing heavily with ripening Sangiovese grapes - the variety that is responsible for making Chianti Classico. During September most towns in Chianti celebrate the Sangiovese harvest with wine festivals such as the Vino al Vino held on the third week in September (17-19) in the small town of Panzano in Chianti, where many local wines can be sampled by the glass.

    For a truly inspiring tour along Chiantigiana road, make time to visit some of the ancient towns of Chianti and surrounding vineyards. Most vineyards are open to the public, but it’s worth checking before you visit. The vineyards recommended below are open to visitors.

  • Greve in Chianti

    Greve is a principle market town 31km south of Florence (Firenze). The Franciscan monastery is still at the heart of the old part of the city, as is the triangular main piazza, where a market has been running more or less continuously for centuries serving the nearby castle communities and hamlets.

    Wineries to visit:

    Villa of Vignamaggio dates back to the 14th century and the winery produces around 230,000 bottles of wine every year, divided between Chianti Classico, Chianti Classico Riserva, I.G.T. and Vinsanto del Chianti Classico DOC. They offer pre-booked guided tours of their gardens and wine cellars, including a wine tasting and lunch. Their shop is open daily from 10.3am to 6.30pm for free wine and oil tastings.

  • Panzano in Chianti

    A small town with Etruscan origins, Panzano is situated on the Chiantigiana road between Castellina and Greve. Panzano Castle, built between the 11th and 12th centuries, nestles at the highest part of the town and the hike through the cobbled streets is well worth it. The piazza is charming and a perfect place to watch the elderly men play cards, sip a Prosseco or enjoy homemade gelato.

    Wineries to visit:
    Le Fonti
    A charming boutique family run winery nestling at the foot of Panzano village. The winery is open for cellar tours and tastings Monday to Friday from 10 - 12 and 2 – 6pm and produces superb IGT and Chianti Classico DOCG.
    Le Fonti

    Fattoria Montagliari
    A small family owned and run farm that has been producing wine using the most traditional methods since 1720. The Migliorini family, bought Fattoria Montagliari in 1999 and produce Chianti Classico DOCG, Chianti Classico Riserva, Brunesco di San Lorenzo IGT, Grappa, Brandy, Extra Virgin Olive Oil, and aged Trebbiano Balsamic (20 and 28 years). There is also a fantastic restaurant with genuine Tuscan cooking and breath-taking views over the Greve valley.
    Fattoria Montagliari

  • Castellina in Chianti

    Castellina in Chianti has historic and noble origins -in the 13th century it was built on a high ridge, probably over Roman ruins. It has a 14th-15th century character with a number of religious structures, including the parochial church of San Salvatore.

    Wineries to Visit:

    Villa Trasqua
    With 50 hectares under vine producing Chianti DOC and IGT wines, Villa Teraqua also boasts 10 hectares of olive trees. They offer guided visits to the cellars.

  • Radda in Chianti

    Radda in Chianti is principle market town in the Province of Siena in the Italian region Tuscany, located about 35 km southeast of Florence and about 15 km north of Siena.

    Wineries to Visit:


  • Gaiole in Chianti

    Gaiole in Chianti is principle market town in the Province of Siena in the Italian region Tuscany, located about 40 km southeast of Florence and about 15 km northeast of Siena. The American magazine Forbes named it number one in its list of "Europe's Most Idyllic Places To Live."

    Wineries to visit:
    The name Ricasoli has been linked to wine since 1141, when Brolio Castle passed into the hands of the Ricasoli family. The family tree, reproduced in a print from 1584, is also one of the first images we have of Chianti. You can book wine tastings for small or large groups at the Brolio wine shop: an exciting way to learn about and appreciate the Chianti Classico area through its most representative wines. The helpfulness and competence of the staff who present the wines will make your experience in the wine shop pleasant and fascinating.

    Casanuova di Ama
    Our farm, Casanuova di Ama, is located in the heart of Chianti Classico, the splendid scenario of the hills of Ama - in the municipality of Gaiole in Chianti.
    At the altitude of 550 metres above sea level there is a total of 12 hectares of land; 5 of which are vineyards, 4 are planted with olives and 3 are forest all which surround the historic buildings of the farm.
    The Bencini family bought the farm in 1967.
    In 1984, after many years of restructuring the buildings and planting new vineyards, we sold our first bottles of wine, the so called Fiaschi (bottles wrapped in baste fibers).
    From then on our little farm started growing, slowly but steadily…
    With patience and passion - two essentials in farming - we established our production of wine, Vinsanto, extra virgin olive oil and Grappa.
    And now we added to our experience of generations of farmers, winemakers and cellar masters the expertise and consultation of the oenologist Yuri Bencini who is following our passion for quality and the principles of our philosophy.

  • Wine tip- It’s all about temperature

    When buying a bottle of Chianti ask the merchant what the vintage (year) was like (was it a hot or cool summer?), in order to gauge the wine’s aromatics. Temperature has an immense impact on the ripening of the grapes during the last weeks prior to harvest and is the key to determining the final aromatics of the wine. In the case of Chianti if temperatures are on the cooler side, the resulting wine will be fresher, more aromatic and abundant in fresh fruit flavours such as cranberry, cherry, and raspberry. If the season finishes with warmer temperatures, the wine will be dominated by plummy, prune-like characteristics.

Experience an official tuscany tour with

Fiat 500 Grand Tour of Chianti and Siena Hills

An incredible opportunity for a deep-dive in the uncompromising beauty of the Chianti classic region, this tour will take you off the beaten path and in the heart of the most beautiful part of Tuscany.

We reach Castellina in Chianti with our courtesy bus and from there we proceed to the driving instructions and an introduction to the day ahead of us. As soon as we hit the road you are immersed in resplendent hills, small hamlet-towns and vineyards, curvy, open roads where every turn deserves a photo stop.

from 230 US Dollar

Overnight Rome Independent Tour from Florence by High-Speed Train

All roads lead to Rome. This 2-day tour makes exploring the Eternal City easy, taking away any stress of booking train tickets, a hotel and sightseeing excursions. After a high-speed train ride from Florence, get on the hop-on, hop-off bus and explore famed sites like the Colosseum, the Circus Maximus, the Vatican, Capitoline Hill, and the Basilica of Santa Maria Maggiore. Sleep in a comfortable three- or four-star hotel, depending on option selected, and continue using the hop-on, hop-off bus to get around before riding the high-speed train back to Florence later that day.

from 271,18 US Dollar

Siena Trip Through the Countryside

Take a trip off of the beaten path through secret gardens, back streets and beautiful panoramas, discovering unique Siena

from 170,25 US Dollar

7-Day Weekly Cooking Class from Florence

The only course with so much potential, you'll be able to learn how to cook a unique meal for every day for a month!

from 2399,53 US Dollar
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