The Black Rooster marks some of the greatest wines in the world.

It is easy to see why Tuscany remains one of our most popular trips. I moved to Italy some 12 years ago to immerse myself in this magic, and have determined that cycling through this region is the ideal way to learn about the place.

On a bike, we leave other tourists behind and get to experience places as they have remained for thousands of years. The epicenter of Tuscany – flanked by Florence to the North and Siena to the South – for its wine, wild boar, small, winding roads and forested hilltops. In the center of Chianti is the ideal, 9th century one-strip hilltop wonder of cobblestones enotecas and cafés known as Radda in Chianti. Ride up to the entrance of Radda in the morning and you’ll find Fabrizio Ferrucci, owner of Bar Dante making panini for the hungry denizens who flock to his café for local treats. Fabrizio will assure you that while Radda is not perfect, it is pretty close.

Visit Tuscany on a Trek Travel bike trip

Radda is so ideal, in fact, that the two warring city-countries of Florence and Siena have fought over it for centuries. Legend has it that late in the 12th century, these two archenemies finally decided to end their bloody land-feud peaceably. By parliamentary agreement, at the first crow of their respective roosters on the appointed day, one knight from Florence, and one knight from Siena would depart on horseback down the road the connects the two cities. At the precise point the two knights meet on their journey, the line would be drawn to divide the Province of Florence from the Province of Siena.

While Siena chose to fatten and spoil a fine, plump rooster, the Florentines were far more devious. They selected a lean, black rooster and locked it in a windowless dungeon without food or water. When the date arrived, the rooster’s hyper-sensitive retinas led him to crow his heart out, giving the Florentine knight a dramatic head start. He reached all the way to Fonterutoli, a territory of Castellina, before he met the Sienese knight. And so they established the border at Castellina, a mere 19 kilometers from Siena’s walled city.

To this day, the internationally recognized symbol of Chianti is a silhouette of Il Gallo Nero, The Black Rooster. It marks some of the greatest wines in the world, and cyclists wear the jersey with pride. Next time you find yourself in Radda, ask Fabrizio about his story. He just may fill you in on some more history of this remarkable area that we are fortunate to ride our bikes through. The rest of the learning comes from the air flowing in your face while you spin down the winding roads, the same roads the two knights thundered down all those years ago.

By Jacob Young, a guide for Trek Travel

Visit Tuscany on a Trek Travel bike trip

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