Gently pedal through the soft hills of Tuscany, their delicate contours marked by lines of sentinel cypress trees. The towns, Certaldo, San Gimingano, Siena, Montalcino … define color coordination, and showcase a local talent for fitting modern style into old stones. The perched villages and “fattoria” olive and wine farms of Chianti are delightful museums to the rustic charm of Italy.
Your Itinerary: Day 1: Cycle to Certaldo, past villas surrounded by their trademark sentinel cypress trees, and through the vineyards of northern Chianti. Certaldo is the final resting place of Boccacio, friend of Petrarque, literary inspiration for La Fontaine fables and Pasolini films. His home, now a museum, graces the old walled town. Our base for two nights. (30-90km) Day 3: Up a big hill to Castellina in Chianti. The climb is long, but the eternal glide back down is most rewarding. Then into Siena, via the dramatic fortress of Monteriggioni. (45-65km) Days 4 & 5: What to say about a place that holds horse races on its town square? Well, you could point out that it is home to a state-sponsored wine bar, offering a hundred open bottles from all over Italy on a given evening…. A novel use of tax funds, and one with which we concur. Siena boasts a pure, aesthetic beauty that has been emulated the world over. In North America, Crayola made it a color. Even Florence, Siena’s eternal rival, has often been shown the way by her more sedate and conservative neighbor – most recently in her attempts to preserve her center from the ravages of the automobile. The harmony of Siena’s shell-shaped central square is a rare and wonderful thing, especially at night when the day-trippers have departed for the evening. So why leave? Well, for one thing, this is a cycle trip…. And there are sights in the surrounding countryside that should not be missed. Use one day for a glorious cycle south. Though Chianti is better-known, the hills south of Siena (“i colline sienese”) may be our favorite Tuscany. No one lives here, and the distances are long, even between “fattorias” (Tuscan farms, the exact opposite of “factory farming” despite their names). The scenery is splendid, and quiet roads make for great biking. Observe the truffle hunters, searching for the elusive “tartufo bianco.” Stop for lunch in front of the Monte Oliveto Maggiore abbey. If you can stand one more climb, struggle up to the wine town of Montalcino, home to the famous “Brunello.” Every third building is a wine bar! Coast back down to the station for an evening train home…. (50-100km) Day 6: We leave our idyllic city, heading for the hills and into the heart of Chianti, to Radda. Roads on top of ridges, typical Tuscan scenes, and not much else line today’s route. If you wish a long ride, the fortified château at Brolio can provide one. The castle has been in the same family since the 11th century, and both its walls and gardens can be visited. (45-60km) Day 7: Marathoners (and those not afraid of city traffic) can make directly for Florence. Cycling into an Italian city is not dull, but you may prefer to seek your thrills elsewhere (and you can attain the same result in less time by simply jumping off a cliff). We suggest instead a route to a local train station, for a quick ride into town protected by a metal box. Either way, we loosely follow the “Via Chiantigiana,” or Chianti Way, north to the Arno valley. Our Tuscan trip disbands upon arrival in Florence on Saturday evening. (30-60km) Notes: - Trip price includes the bike! 
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