Chianti Cycling Tours
Bicycling on the glorious roads of Tuscany

Chianti Farm Roads near Castellina in Chianti

Booking the Bicycle Tour Packages: IV Travel

• Tour 1 – The Monteriggioni Ride
  Half day from Casalecchi.  Easy to moderate ride.  A chance to “get your legs”.

  During this 31 km. (10% offroad) mountain bike ride towards the southern borders of Chianti we’ll visit the famous fortified town of Monteriggioni, one of the best preserved medieval hilltop villages in Italy. Riding inside its mighty walls is like jumping back in time of about 800 years, when pilgrims travelling along the via Francigena on their way to Rome stopped here for a prayer in the Romanesque-Gothic parish church of Santa Maria. On our way back we’ll pass the ancient village of Fonterutoli (dating back to the end of the 10th century), one of the last military posts of the Florentine Republic during the 300 years wars against Siena.
  
  

• Tour 2 – The Val D'Elsa Ride
  Full day – including lunch at a local restaurant – moderate

  Riding the scenic hills along the western side of Chianti Classico we’ll visit the historical centre of Castellina cycling inside the suggestive via delle Volte, a vaulted roof alley which was part of the medieval fortification of this  town. The ride continues with ups and downs along a very  panoramic ridge before a long exciting downhill towards the Elsa Valley, passing the imposing crenellated Castle of Paneretta. 44 km. all on asphalt country byroads.
  
  Highlights of the ride:
  
  ~ The Medieval town of Castellina, fortified by the Florentine Republic at the end of the 12th century and consequently chief town of one of the terzieri (= administrative thirds), into which the Commune of Florence had divided the Chianti League.
  ~ The castle of Paneretta, transformed into a villa during the Renaissance and now a famous winery which production of wine is recorded as early as 1596.
  ~ The Romanesque parish church of San Pietro a Cedda, built around the middle of the 12th century.
  
  

• Tour 3 – The Radda-Panzano Ride
  Full day – including lunch at a local restaurant – moderate to difficult

  During this demanding 37 km. (50% offroad) mountain bike ride along the ancient borderline between the Florentine Republic and the Senese Republic (scene of many battles between the 2 cities for about 300 years  during the Middle Ages), we'll be biking across suggestive medieval hamlets that dot the countryside.

  Highlights of the ride:

  ~ San Polo in Rosso, a marvelous example of a fortified parish church, first mentioned in a document dated 1070.
  ~ The ancient village and castle of Ama, dating back at least to the 11th century and fortified in that period, to the extent that in 1219 it is mentioned as a castle.
  ~ The castle of Monteluco a Lecchi, which appears in documents from the 11th century on (and which was  constantly attacked by the Senese Republic for its important strategic position on the border).
  ~ The small village of San Sano, dating back to medieval times as proved by the architectural features of the  buildings and the imposing truncated tower, which was  probably the garrison tower of the old fortification. (A longer but easier 49 km. (30% off road) version of this ride is available upon request).
  
  

• Tour 4 – The Chianti Classico Ride
  Full day – including lunch at a local restaurant – moderate to difficult

  Demanding 45 to 50 km. (45% offroad) circular loop  across scenic hills covered with vineyards, olive groves and woodlands in the very heart of Chianti Classico.

  Highlights of the ride:

  ~ The picturesque medieval village of San Donato in Poggio, established in the Etruscan period (3rd to 2nd centuries BC) but documented since the 11th century, when it was fortified."
  ~ The tiny hamlet of Sicelle, documented as early as 1077.
  ~ The parish church of San Leolino, one of the most ancient  of Chianti, recorded in a document dated 982 and important place of prayer for pilgrims.
  ~ The castle of Panzano, dating back to the early 12th century and part of the defensive belt of the Florentine Republic during the Middle Ages."
  ~ The village and castle of Volpaia, mentioned since the 12th century and now a very interesting winemaking village.
  ~ The medieval town of Radda, first mentioned in a manuscript of 1002 and chief town of the Chianti League from the late 13th century during the wars against Siena.