A tour for serious riders as well as connoisseurs of culture and history, this adventure starts and ends in the fabled city of Florence. Firenze, as it’s known to the locals, is worth a voyage across the Atlantic all by itself. Our first riding day in Tuscany snakes through the Chianti Classico region. As the first pages of this picture-book tour unfold, the hills fade into a grayish blue with stone pines, “castelli“ and “centri storici“ flashing by as we roll towards Siena. The city of Siena steems with culture and history.

This is where the Palio, the legendary historical horse race, gallops through the “Piazza del Campo,“ Siena’s main square and emotions reach the boiling point as the fierce rivalry between the “Contrade“ renews its centuries-old tradition. The trip to Assisi will be one of spiritual renewal. At Madonna della Cima, high above Gubbio, we’ll behold the beauty of Umbria. Next, we push off for San Marino, the city that is a country unto itself. Our final rest day can be used to explore the great castles and fortresses of Montefeltro. After this reprieve, we come upon our grand finale: a jaunt through the mountain passes across the Alpi di Serra and Casentin on our way back to Florence.