Get ready to live out your Italian cycling fantasies on the ultimate trip through Tuscany. With five days of stunning rides—including sections of the historic Via Francigena, an ancient route that’s connected Canterbury to Rome for over 1,000 years—you know you’re in for quite the adventure. You’ll conquer tough—yet rewarding—climbs around San Gimignano, ride to wine tastings at vineyards in Chianti, and cruise through picturesque pastures and hillsides in the Val d’Orcia region. Along the way, medieval towns and castles await (you’ll even have the chance to dine in one!), as well as food so spectacular, it’s what put Tuscany on the map as a culinary hotspot. This is the land of pecorino cheese and pappa al pomodoro (Tuscan tomato and bread soup), after all. We’ve got all the gear and professional cyclist-curated routes waiting—all you need to do is take the plunge and jet over to Tuscany.
Fly to Florence
Arrival in Florence and transfer to Val d’Orcia region
D1
Val d’Orcia region to Mill Val d'Orcia bike ride, lunch and tour of pasta production plant & optional Montepulciano wine tasting
D1
Val d'Orcia region to Montalcino ride, Montalcino to Val d'Orcia region bike ride & optional Pecorino cheese farm & dinner
Siena walking food tour, travel to Chianti region, and castle tour & dinner with wine tasting
D1
Chianti region to Greve in Chianti & Greve in Chianti to Chianti region bike rides
D1
Chianti region to San Gimignano region via Radda in Chianti bike ride & dinner in San Gimignano
D1
San Gimignano region to Monteriggioni loop bike ride, walking tour of Monteriggioni & Strove loop bike ride
Fly home
Travel to Florence & walking tour of Florence
Optional visit to Pitti Palace & the Boboli Gardens & free time in Florence
Fly home
Hotel