• Radda in Chianti - The region surrounding the capital has been inhabited since 2000 BC, as shown by the archaeological site of Poggio la Croce, where remnants of an ancient village have been uncovered. Excavations over the past decade have revealed numerous artifacts. Although few traces remain, it is believed that an Etruscan village once existed here. By the fall of the Western Roman Empire in the 5th century, small rural settlements had already formed in the area, including Castelvecchi, Monterinaldi, Volpaia, and Radda itself.

During the 9th and 10th centuries, the Radda area saw the emergence of feudal society, leading to the construction of villages. The first documented mention of Radda is in a diploma from 1002, where Emperor Otto III confirmed a donation by Countess Willa to Badia Fiorentina. Radda is frequently mentioned in documents from Badia Fiorentina until the 12th century. “Ramda judicaria fiorentina et fesulana” is noted in a document from Badia a Coltibuono in 1041.

On May 25, 1191, Emperor Henry VI granted the castle of Radda and its court as a fief to the Counts Guidi. This fief was later confirmed by Emperor Frederick II, although by the 13th century, Radda was under Florence’s control. The castle was raided by the Sienese in 1230 and occupied by French troops led by Charles I of Anjou in 1268. Radda faced another occupation and significant looting during the second Aragonese invasion in 1478.

Administratively, Radda was the capital of the Chianti League, which included Radda, Gaiole, and Castellina. From the late 13th century, it became the seat of a podestà appointed by the Florentines, and in the municipal statute of 1415, Radda was confirmed as the League’s capital. Among Radda’s podestàs was Francesco Ferrucci.

In the 17th century, after conflicts ended, castles were transformed into stately villas where owners focused on wine production. Radda in Chianti was visited in 1773 by Grand Duke Pietro Leopoldo, who found it quite remote. Following his visit, roads were improved, but Radda remained poor and isolated. The affection for the Habsburg-Lorraine dynasty persisted, as evidenced by the 1860 plebiscite for Tuscany’s annexation to Sardinia, where Radda voted against (281 yes out of 581 voters, out of 879 eligible).

This situation peaked in the 1950s when countryside depopulation, common in many Chianti areas, reached its height. In the 1970s, these places were rediscovered, and gradually, all castles, villas, and farmhouses were restored, with new farmhouses and farms established.

• Panzano in Chianti - The Panzano area was inhabited during Etruscan times, as evidenced by a stele from the 6th-5th century BC found at the parish church of San Leolino, though it has since been lost. The area was also densely populated in Roman times, with numerous traces in toponyms, including Panzano itself. In the early 10th century, the parish church of San Leolino in Flacciano was mentioned, later becoming Panzano.

The first recorded mention of Panzano is in the 12th century, in “plebe Sancti Leolini sitam in Panzano,” while in the late 13th century, the church of Santa Maria in the castle is also noted. The castle of Panzano likely developed before the 12th century and was owned by the Firidolfi family.

Few historical records of the castle remain. In the mid-13th century, when the Florentine countryside was organized into leagues, Panzano was included in the Lega della Val di Greve. After the Battle of Montaperti in 1260, the castle was sacked, and two towers were destroyed by victorious Ghibelline troops. During the war between Florence and the Visconti of Milan, Panzano was occupied and sacked again by Alberico da Barbiano’s troops in 1397.

In 1478, Sienese troops and their allies, the troops of King Ferdinand II of Naples, invaded Chianti for the second time. The castle of Panzano was a crucial defense for the Republic of Florence, becoming the seat of the Republic’s Commissioner. After the fall of the Republic of Siena in 1555, Panzano was not involved in warfare until 1944.

• Castellina In Chianti - The Montecalvario mound, an Etruscan tomb near the town dating to the 7th-6th century BC, and the Necropoli del Poggino near Fonterutoli, confirm the Etruscan presence in the area. Excavations since the 1980s in Castellina indicate a large town once existed, likely located in Salinvolpe, a few hundred meters from modern Castellina.

More evidence from the medieval era exists. The first documents date to the 11th century when the area was a fief of the Castello del Trebbio nobles, related to the Counts Guidi. In the 12th century, Castellina came under Florence’s influence, and in 1193, an agreement allowed Florentines to militarily oversee the castles of Trebbio and Castiglione (now Castellina). After the Lodo di Poggibonsi in 1203, which defined Chianti’s borders between Florence and Siena, Castellina became a key Florentine outpost on the main road connecting the rival cities.

In the 14th century, Castellina became a cornerstone of the Lega del Chianti, leading one of the thirds into which it was divided. The Terziere di Castellina administered the Chianti area descending towards Valdelsa. In 1397, it was sacked and burned by Duke Gian Galeazzo Visconti’s troops, led by Alberico da Barbiano. In 1400, it was decided to fortify Castellina, as recorded in the State Archives of Florence: “On site qui dicitur la Castellina fiat fortilitia.”

The work progressed slowly, and in 1430, workers from the Opera del Duomo were tasked with fortifying Castellina, Staggia Senese, and Rèncine. Filippo Brunelleschi was sent to determine the necessary interventions and estimate costs. In 1452, Castellina’s walls withstood an Aragonese assault. However, in 1478, during the second Aragonese invasion of Chianti, Castellina was conquered by Sienese and Neapolitan troops. Giuliano da Sangallo directed Castellina’s defense, while Francesco di Giorgio Martini commanded the besiegers. The Sienese occupation lasted until 1483 when the Florentines regained control.

In 1774, with Grand Duke Pietro Leopoldo’s administrative reform, Castellina became the seat of the Community, from which the current municipality derives.

• Wine tasting
• Lunch
• Tour Guide
• Use of helmet

As we meticulously handle all specifics, bid farewell to disarray, and relish Tuscany’s exquisite scenery from the comfort of your trendy vespa, a perfect vehicle not merely for bypassing congestion but for experiencing the authentic Italian lifestyle. Our itinerary for the day is flexible, allowing for multiple stops to explore the Chianti region, home to medieval towns, breath-taking vistas, and some of the world’s top wine manufacturers. We’ll provide access to one of the region’s premier wineries and impart the secrets behind its millennia-old wine production process. At the end of our tour, we’ll visit an organic farm and cellar, before relaxing on the terrace offering panoramic views of the vineyard-draped hills. We’ll serve a local Tuscan lunch, created using traditional fresh ingredients and complemented with a specialist selection of wines. Representing more than just a symbol and lifestyle, this is a unique memory etched in time. Prior scooter or motorbike experience is required.

• We require experience with scooters or motorbikes
• Minimum age for driving is 18 years
• A driving license is requested
• Please note that a briefing with Vespas will be lead by members of our staff and they will evaluate client skills and will decide if renting or not the Vespas, their decision will be unquestionable. The tour will start with a different vehicle up to our availability

For a full refund, cancel at least 24 hours before the scheduled departure time.