To venture into Tuscany's enchanting Chianti region, located between Florence and Siena, is to discover a cyclist's paradise. Biking routes abound for those who wish to cycle off-the-beaten-path in a region painted in picture perfect panoramas of vineyards, olive groves and vast farmland. A maze of winding biking trails and rural roads meander through the rolling valley terrain, gradually leading to hilltop towns. Stretching through Tuscany, cycling routes range in levels from easy to strenuous for amateur to veterinary cyclists.
In this sun-drenched region with its green patchwork of lands, there is much to see and do while cycling. Breathtaking vistas of ochre fields punctuated by swathes of red poppies and golden-ripe sunflowers serve as the backdrop to magnificent panoramas of ancient villages perched on the hillsides. Lined with the occasional oak and olive groves, the roads unfold into an infinite horizon of verdant and wine colored grapevines.
The Chianti Loop circles through medieval towns steeped in regional history. Encircled by their ancient ramparts, these villas boast clusters of Romanesque churches, abbeys, castles and fortresses. In the heart of Tuscany, Greve in Chianti, a large market town, sits at the crossroads of an ancient trade route between Florence and Siena. Delightful communities, such as Montefiorale and Panzano surround the town, where castles turned patrician homes spatter the landscape. In its stone houses and paved streets, Montefiorale reflects its medieval architecture, and Panzano's Romanesque church of San Leolino is home to precious works of art.
From Greve, loop through the main Chianti towns. Castellina in Chianti is nestled around a 13th century castle. The town's origins date back to Etruscan times, its importance due to its strategic location. Along the ancient ramparts, the towering fortress offers stunning countryside vistas, and an impressive underground tunnel, the Via delle Volte, wraps around the city, today housing shops and restaurants. This is the spot for a short break for tired limbs and taste a delicious gelato.
A long descent with sweeping panoramas of vineyards and olive groves across the Val d'Elsa (Elsa Valley), followed by a graduate ascent, terminates in Colle Val d'Elsa, a village blamed for its crystal glassware. Perched on a hilltop overlooking the Elsa River, Colle Val d'Elsa, a historic town on the Via Francigiena, the road used by pilgrims from Rome to northern Europe, developed in three districts. Upper Colle preserves its 14th and 16th century fortifications, buildings, old gates and medieval sights, such as the ancient tower house and Campana building, which are architectural masterpieces. From here, San Gimignano is just a short jaunt away.
Looping around, the Chianti biking route continues to Radda in Chianti, a beautiful town enclosed in large defensive ramparts. Characterized by its narrow streets converging into a main piazza, Radda maintains its medieval charm. Numerous castles and churches, among them the castle of Volpaia and the Romanesque church of Santa Maria in Prato, nestle in the surrounding hills. Not far, Monteriggioni conforms perfectly to the model image of a walled community, with its ramparts and towers essentially intact and giving way to original attractive buildings.
After an arduous day of cycling, the Badia a Coltibuono, historically a monastery, offers the perfect end to an adventure-packed day. Famed for its wines and prized olive oil, the Badia features agrotourism accommodations in a gorgeous setting to relax with a drink, take in the view and spend the night.