Agritourism in Florentine Chianti - The chianti
Ride through classic Tuscany, enjoying Chianti's villages, food and wine
The Tuscan landscape is surely one of the most evocative and romantic in Europe. Cypress trees, olive groves, vineyards, ancient hill top towns and, of course, classic Renaissance cities. Basking in the the southern sunshine, this is Italy at its very best. Our two-wheeled exploration is carefully planned to take in the best this area has to offer without feeling rushed or over-cultural – part of the joy of the Italian lifestyle is having time to sit and watch the world go by with a glass of Chianti. Working our way south we pass the high towers of San Gimignano and Siena’s magnificent Campo before entering ‘Le Crete’, Tuscany's less-visited, but equally scenic south. Those wishing to enjoy Florence can choose to arrive a day early to enjoy this magnificent city.

Chianti, where for centuries the famous wine Chianti Classico has been produced is a part of Tuscany delimited at the North by the outskirts of Florence, at the East by the Chianti Mounts, at the South by the city of Siena, at the West by the Pesa and Elsa Valleys, through which runs the “Palio motorway”.
The main towns of the Chianti region are Siena and Florence. The area is equally divided between the provinces of the two towns. It is an area of 70.000 hectares which entirely comprise the towns of Castellina in Chianti, Gaiole in Chianti, Greve in Chianti and Radda in Chianti, and partially the towns of Barberino Val d’Elsa, Castelnuovo Berardenga, Poggibonsi, Certaldo, San Casciano in Val di Pesa, and Tavarnelle Val di Pesa.
The region of Chianti, with its hills of superb beauty, is in the heart of Tuscany. It is difficult to define its borders because only the Mounts of Chianti to the east naturally and clearly separate the area from the Valdarno Superiore; the remaining territory gradually flows into the hills of Arbia, Elsa, Greve and Pesa. Medieval boroughs, castles, churches, abbeys, monasteries, farmhouses and villas appear one after the other in a fantastic itinerary which exalts the laboriousness and creativity of man; centuries of work have shaped the hills of this region and the succession of vineyards, olive groves and woods create a unique harmony. The suggested itinerary is the Via Cassia, a rural route which runs through the classic wine region, like the other famous Chiantigiana route.
The landscape is unforgettable, always varying and harmonious and very changeable in colours and atmosphere according to the seasons. There are many possible detours to suggest to visit a church, a castle or an isolated borough, silent witnesses of the historical and artistic wealth of Chianti.
A Chianti itinerary along the Cassia route
San Casciano Val di Pesa
Among the main monuments, the Collegiata and church of the Misericordia (or Santa Maria al Prato) which contains a rich patrimony of works of art including a Crucifixion by Simone Martini should be noted.
The conspicuous number of churches testifies the historical importance of San Casciano in the Middle-Ages; some of the churches deserve particular attention: S. Cecilia a Decimo just outside the village, the Romanesque church of S. Giovanni in Sugana on the way to Cerbaia and the church of S. Stefano a Campoli (dated 903) near Mercatale Val di Pesa.
Among the many villas in the area of San Casciano, villa I Collazzi and villa Tattoli near Cerbaia, and villa Bossi-Pucci the so-called l’Albergaccio where Nicolò Machiavelli stayed during his exile from Florence, should be mentioned.
Tavarnelle Val di Pesa
Tavarnelle is named after the “tabernulae”, the resting places along the “Via Regia” (Royal Route) which connected Florence to Siena, and subsequently Rome. Of great interest the many churches in the area.
From Barberino Val d’Elsa towards Certaldo
At the end of the ’500, along the road which links Barberino to Certaldo the chapel of Archangel Michael was built, from a plan by Santi di Tito to commemorate the destruction of the medieval town of Semifonte.
Another important monument is the Romanesque church of S. Appiano, one of the oldest in the Florentine countryside, dateable to the XI century.
After Barberino Val d’Elsa the via Cassia leaves the Chianti area going through the towns of Poggibonsi, Colle Val d’Elsa, Monteriggioni and ending in Siena. A detour from Poggibonsi to visit San Gimignano is recommended.