Chianti by Bike

Cycling the Wine Roads of San Gimignano and Chianti Classico

Tour Overview:

  • Bike in two distinctive regions of Tuscany: Chianti Classico and San Gimaigno
  • Enjoy post-ride wine tastings at Castelo Brolio, Vecchie Terre di Montefili, Panizzi, and Cesani
  • Refuel with gourmet wine dinners featuring Tuscany’s cucina rustica
  • Visit Bocaccio’s birthplace in Certaldo and Gaiole and Radda, both part of the medieval Chianti League
  • See Italian Gothic masterpieces of art in San Gimignano and Siena
  • This tour covers two subregions within the ancient heart of Tuscany. We begin in Chianti Classico. Lying between Florence and Siena, this sprawling, forested land was contested by the rival city-states for nearly 400 years, and its fortified towns and storybook castles testify to that history of warfare. Here you’ll find crenulated castles, stone farmhouses trellised with roses, country lanes flanked with cypress rows, and hand-built stone walls enclosing ancient olives groves. It’s picture-postcard Chianti, its charming character carefully protected by locals.

    The second part is around San Gimignano. This beautifully preserved medieval city was a stop on the Via Francigena, a pilgrimage route that lead from Canterbury to Rome, connected by abbeys. In 1348, the city was brought to its knees by the Black Death (bubonic plague) and development ceased, so what remains today is essentially a medieval village frozen in time, its ancients walls, city gates, and numerous towers as they were during the Trecento.

    For modern-day cyclists, both areas offer quiet back roads and impeccable landscapes. We’ll follow some designed wine roads and castle roads, cycle through cool forests and open farmland, and see plenty of vineyards. Where there’s vines, there’s hills, so these rides should offer enough challenges to satisfy seasoned bikers.

    The sample itinerary for CHIANTI BY BIKE is structured with dual activities in mind. During the first part of the day, we bike. In the later afternoon, we’ll have time to relax and visit the wineries for a private tour and tasting. (We arrive by van, not bike; contrary to some people’s preconceptions, we never bike from winery to winery.) Of course, since this is a customizable tour, we can tailor it to your interests. If you want more miles and less wineries, no problem. Or vice versa. We can add or subtract days or regions, or substitute higher-end or more economical accommodations. Just give us a call to discuss your ideas, budget, and projected dates. All you need is a group of four or more bikers for your dream biking vacation.


Dispatches from the wine road
– Livin' La Dolce Vita


National Geographic Traveler
– See our award-winning trips


News, tips, recipes every month
– Sign up today