This scenic and culturally fascinating region between Florence and Sienna is considered to be classic Tuscany. Vineyards, cypress trees, forests, idyllic wine villages and castles are nestled in the gently rolling hills. During the Middle Ages, Chianti was the scene of heavy fighting between the Tuscan cities of Florence and Sienna, a conflict that ended in 1559 with the annexation of Sienna by Florence. Since the best wines in Italy are made here, the name “Chianto Classico” has been a protected trademark since the 18th century. It initially included Radda, Castellina and Gaiole. Other areas to the East were added later.
Pleasant loop trail through vineyards and shrubland
This medieval abbey in the vineyards southeast of Florence is today a renowned winery. It is also the starting point for a pleasant walk through a delightful cultural landscape that will lead you down to the Pesa River. (2 hrs, 30 min, 9.5 km, total vertical distance: 290 m)
Through the vineyards to the gates of Sienna
On a mountain path just a few kilometers from the cultural center of Sienna, you can enjoy some relaxation and a view. The cathedral of Sienna is visible for the entire walk. The goal of this leisurely stroll is a 14th century Carthusian monastery, the Certosa die Pontignano. Afterwards, you can stop for a bite to eat at the Osteria La Piccarda. (2 hours, 8.5 km, total vertical distance: 140 m)
Modern art in an oak forest
In the early 1990's Piero and Rosalba Giadrossi discovered this seven-hectare oak forest near Pievasciata. It offered the ideal conditions for their project – to present modern art in a natural context. The park opened its doors after five years of hard work. More than 20 artists from all over the world exhibit their work here. The peaceful surroundings lend their art a unique charm.
Hermits in a dense forest
Back in the Middle Ages, when Tuscany was being deforested, one forest was spared – the Bosco di Lecceto. Numerous hermits came to live here, and their traces can still be seen today. This is especially true of the Eremo di Lecceto, which is also the starting point for the hike we recommend. You can follow the beautiful trail through a forest that is every bit as dense as it was 800 years ago. (3 hrs, 11 km, total vertical distance: 279 m)
Medieval castles and hidden hamlets
This wine center with a vivacious downtown is nestled among forests and gently rolling hills where Romanesque churches, medieval hamlets and a castle are tucked away. This magnificent hike will lead you around the Monte Marcoli. On the way, you can stop for a bite to eat at the Ristorante L'Alto Chianti or afterwards in Gaiola. (3:50 hrs, 12.8 km, elevation change: 350 m)
Center of the Chianti Classico
The center of this lively wine village is the triangular Piazza Matteotti, where the weekly market and the annual wine fair are held. Arcades and townhouses with chic boutiques and expansive balconies give the place a special atmosphere. In its center the statue of Giovanni da Verrazzano: a seafaring man and native of Greve who landed on the American east coast in 1524. Above town in a picturesque hill setting lies the medieval castle village of Montefioralle.
According to legend, Siena was founded by Senio, the son of Romo, who was one of Rome's founders. Siena is the most important city of art in Tuscany after Florence. The city's main period of development was the Middle Ages, when the town expanded in various directions. Siena reached its full splendor in 1300, when most of the civil monuments were constructed, and an attempt was made to build the new Duomo. Siena was pre-eminently a Ghibelline town, and its rulers often “crossed swords” with the Florentine Guelphs in epic and bloody battles that shaped the history of the Italian Middle Ages. One of the most famous battles took place in Montaperti on 4 September 1260, when the Sienese defeated the Florentine army. A tragic plague epidemic in 1348 marked a very difficult period for Siena that led to its annexation into the Grand Duchy of Tuscany and the loss of its independence.
Vineyards, olive groves and a former castle town
This wine-growing village is among the most beautiful towns in Chianti. This goes for the surrounding area as well. Here, roads lined with cypress trees lead to vineyards, scrubland and olive groves. The crowning feature of the landscape is Castelvecchi, a former castle town with a lovely park. After a short yet richly varied walk, you can relax in one of the local restaurants. (2 hrs, 6.5 km, elevation change: 220 m)