Grand Tour of Florence Chianti area
A ring of more than 93 miles (150 kilometers) to explore all of Chianti area of Florence, cycling between the towns of Greve in Chianti, Radda in Chianti, Barberino Tavarnelle and San Casciano Val di Pesa.
The good physical training required is rewarded with the beauty and historicity of the places visited, including ancient villages, castles and especially the picturesque vineyards of Chianti Classico.
The point of departure and arrival is the municipality of Greve in Chianti. Upon reaching Radda in Chianti, the itinerary intersects with the Grand Tour of the Chianti area of Siena, the loop that also encompasses the Sienese stretch, thus offering the possibility of visiting all of Chianti over several days.
You’ll be immediately put to the test with the Sugame Pass, a pretty 4-mile (6.4-kilometer) climb with 988 feet (301 meters) in elevation, which prepares you for the more challenging climb that goes from the junction for Lucolena to the Morellino Pass, the highest point in Chianti on Monte San Michele. From here, you have a steep descent to be taken with caution. Don’t be too distracted by the vineyards, farms and ancient hamlets such as Badiaccia Montemuro, the counterpart to Lucolena and Torsoli on the Sienese side. This brings you to Radda in Chianti (home of the ancient Lega del Chianti) where you can rest while visiting the village and the Wine Museum at the Casa Chianti Classico.
The route takes you back to the municipality of Greve in Chianti through the “Conca d’Oro”—the Golden Valley—of Chianti marked out by the Pesa River. An easy, mostly downhill ride will help you recover from any fatigue. Touching on the villages of Lucarelli and Panzano, you’ll pedal accompanied by views of the beautiful Chianti Classico vineyards.
From Greve in Chianti, set off again in the direction of Barberino Tavarnelle, with a short stretch characterized by some difficulty thanks (or no thanks) to two climbs. The first takes to the charming village of Montefioralle before continuing to the beautiful Abbey of San Michele Arcangelo in Passignano, which is definitely worth a stop if only to admire the scenery. The second climb starts from the village of Sambuca and reaches Tavarnelle Val di Pesa, not far from Barberino Val d’Elsa, with which it forms a single municipality. The choice of where to stop for a rejuvenating break is yours!
From Barberino Tavarnelle begins a challenging stretch through the territory, touching Petrognano and the striking Semifonte, the legendary city destroyed by the Florentines and now remembered by the beautiful dome of the Chapel of San Michele Arcangelo, inspired by Brunelleschi’s work on the Cathedral in Florence. From here, through hills streaked with vineyards, you reach San Casciano in Val di Pesa, an ancient post station with mighty city walls on which stands an imposing deer statue, the work of Mario Merz.
From San Casciano in Val di Pesa, you then pedal in the direction of Sant’Andrea in Percussina, the ancient home where Niccolò Machiavelli wrote “The Prince.” Florence is not that far away but our route continues to Mercatale Val di Pesa and Montefiridolfi with its beautiful castle. After passing the ancient Parish Church of San Lorenzo in Campoli, you get to the Passo dei Pecorai (Pecorai Pass) near the Greve River. In the past, this valley floor was the long favorite stopping place of Maremma shepherds on their transhumance from Maremma to Casentino.
From Passo dei Pecorai starts the last stretch of our itinerary in Florence Chianti area, stopping in the village of Chiocchio, the Castello di Mugnana, Cintoia and its mineral waters, La Panca and the village of Dudda, until the climb in the opposite direction to the Sugame village before arriving back in Greve in Chianti.