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Private Chianti Wine Tour from Florence

Tuscany - Chianti - panorama
Chianti - vignetiTuscany - Chianti - houseSiena - Chianti VinerySiena - Chianti vineraydsSiena - Chianti LandscapesSiena - Chianti - Wine Tasting  Capannelle

From: $95.69

tour duration

4 Hours

start time

09:30 AM & 02:00 PM
Mon, Tue, Wed, Thu, Fri, Sat, Sun

meeting point

Pick-up at your hotel, more details at booking




You will depart with your private driver for a full day excursion to the ancient and scenic Chianti wine region.

The Chianti Classico region is considered one of the oldest wine regions in the world, its oldest wines dating back to the 13th century. That said the Canaiolo grape used in Chianti wines is older than the Romans and was in fact referred to as the Etruscan Grape.

As you make your way through the lush countryside, you will be able to see many wonderful medieval castles that hark back to ages past, making it seem as though you are travelling back in time. You will arrive in the small village of Greve in Chianti. Visit of the historical city center. After the visit of Greve continue to a local wine estate where you will be taken on a tour of the vineyards the cellars and the elegant Italian garden of this beautiful corner of the Chianti.  At the end of this tour, you will have a wine tasting of 3 local wines, Olive oil and local cheese.

After the tasting, you will be returned to your accommodations in Florence.


– Round trip transportation with private car

– Expert English speaking driver and guide

– Independent visit of Greve in Chianti

– Visit of local wine estate (Vineyards, Cellars and Gardens)

– Tasting of 3 local wines

– Tasting of Olive oil and local cheese


– Tuscany landscapes

– Chianti Hills

– Greve in Chianti

– Wine tasting

– Confirmation will be received at time of booking

– Voucher and detailed operator information, including local emergency numbers will be received three weeks before the date of your tour.

– Adult pricing applies to all travelers.

Departure point:

Pick-up at your accommodation

4 hours

Return details:
Drop-off at your Accommodation

Chianti Wine Region

Tuscany - Chianti - panorama
Chianti - vignetiBotti Vino - TuscanySiena - Chianti VineryFlorence - Typical TagliataSiena - Chianti vineraydsSiena - Chianti LandscapesTuscany - Chianti - houseTuscany - Chianti - viewSiena - Chianti - Wine Tasting  Capannelle

Chianti Classico refers to an area in the Chianti region renowned and protected for its wine production. Considered the oldest and most important area of Tuscany, the borders stretch between Florence and Siena (respectively north and south), and between Val d’Elsa and Val d’Arno (respectively west and east).

The region was established as far back as the 12th century, where vineyards were raised on the verdant hills and produced wine locally. Over the centuries, the area grew progressively more famous for its high quality wine production until Cosimo III de’ Medici, the Grand Duke of Tuscany, issued an edict in 1716 protecting the region as the only one allowed to officially create Chianti wine. Over the years, the Chianti Classico region expanded and today it covers a very large area that includes 14 municipalities.

Chianti Classico also refers to any of the seven wines produced in the region. These wines are marked as superior to the rest by the Black Rooster seal on their labels; this seal guarantees their quality and legitimacy, since wine fraud is a very real threat to the industry.

Things to see

Radda in Chianti

Located in the Chianti region is Radda, a beautiful medieval town resting on a hill top between the valleys of Arbia and Pesa. The area has been inhabited by the Etruscans as far back as 2000 BCE, and a document from the 2nd century confirms the existence of a settlement named Radda. In the subsequent centuries, the settlement grew into a village, leading to the birth of a feudal society and the construction of medieval fortifications, some of which can still be seen today. When Radda eventually fell into the hands of the Republic of Florence in the 13th century, the town became the capital of the Chianti League as well as the seat of the Florentine governor, who lived in the beautiful Palazzo del Podestà. The historical centre was badly damaged during World War II but it has since been renovated and restored. The nearby Church of San Niccolò, which was also damaged and restored, is an ancient Romanesque church first built in the 13th century, with various improvements and extensions occurring over the years and giving it its present appearance.

Close to the town square is a more recent and curious monument: the Ghiacciaia of the Grand Duke of Tuscany. Built in the 19th century, this peculiar pyramid-shaped construction served as an ice box, preserving snow and turning it into ice.

Not far from this square is the Grand Duke’s Ice house, built at the end of the 19th century to preserve snow and turn it into ice. The Museum of Sacred Art of Chianti deserves a visit. Set in the Franciscan Convent of Santa Maria in Prato, it displays several works of art from the Chianti region, including a valuable polyptich by Neri di Bicci (1474) depicting the Virgin Mary with child and saints.

In the surroundings of Radda you’ll find many castles and parish churches, such as the medieval Castle of Volpaia and the Romanesque Church of Santa Maria in Prato with beautiful flowered capitals in the Romanesque style.

Today, Radda in Chianti and its surroundings are famous destinations for relaxing holidays in Tuscany. Several restaurants and wine shops in town offer excellent Tuscan dishes and the opportunity to taste the Chianti Classico DOC produced in the area. A quick stop at the tourism office within Radda will help you find the nearest winery open for tastings on the particular day you visit.
Gaiole in Chianti

The city of Gaiole in Chianti is another important city within the Chianti Classico region, located along the river Massellone and on the road connecting Chianti to Valdarno. Thanks to this position, Gaiole has always played an important role as market center for the castles and towns nearby.

I have to say that the main attractions in Gaiole in Chianti are the wineries in its surroundings. Since it was a marketplace, it never had the need for defensive walls such as those in Radda in Chianti. In fact, its center was destroyed and rebuilt many times, and few buildings have been preserved from the past.

Despite this relative “newness”, I still recommend a stop in Gaiole for a short walk before moving on to your next destination. In fact, the real attractions of Gaiole, beyond its Chianti Classico wine, are its surroundings which include beautiful castles and parish churches.

Among the most beautiful is the Parish Church of Spaltenna, displaying a valuable 15th century crucifix, the Castle of Vertine,a small medieval walled village, and the Abbey of Coltibuono, a former monastery now turned into a wine estate.

Another important castle in the area I highly recommend visiting is the Castello di Brolio. Founded by Longobards, it has been home to the noble Ricasoli family since the 12th century who has produced wine for centuries. Descendants of the family still live in the castle so while you can’t visit the castle, I recommend you visit the gardens from where you can admire the breathtaking view of Chianti with the city of Siena at the horizon

San Gimignano

San Gimignano - tetti
San Gimignano - panoramaSan Gimignano - palazziSan Gimignano - view from the top

Located in the province of Siena in Tuscany is San Gimignano, a small medieval hill town surrounded by a lush green landscape. Famous for its architecture and the many towers that mark its unmistakable skyline, San Gimignano is a fascinating town well worth the visit.

The walled town grew around the Church of San Gimignano, later nicknamed Castle San Gimignano, during the 6th century, adopting its name. During the middle ages, the town was located right along Via Francigena, an ancient pilgrim route, and as a result became a popular stopping point for travelers. The richness of the land around San Gimignano also influenced its importance and wealth, birthing an active trade industry.

Things to see

In 1200, San Gimignano claimed independence from the bishops of Volterra, who had ruled it up to this point. Many churches and public buildings were erected during this time. Between the 12th and 14th centuries, during a period of conflict between the Guelphs and Ghibellines, the wealthy families of the town built tower houses, one more impressive than the last, to both defend their land and rival each other. By the end of the medieval period, there were 72 towers, the tallest reaching nearly 70 meters in height. Although San Gimignano escaped destruction from wars, catastrophes or urbanization, sadly only fourteen of these towers remain standing today.

Other notable examples of the medieval architecture of the town are the historic city centre, deemed a UNESCO World Heritage Site in 1990, the Piazza della Cisterna, and the Palazzo Comunale. The two biggest churches, the Collegiata in the Piazza del Duomo and the Chiesa di Sant’Agostino, both contain beautiful frescoes and other important artworks by artists such as Domenico Ghirlandaio, Benozzo Gozzoli and Taddeo di Bartolo.