Italy Biking: Tuscany

Get ready to live out your Italian cycling fantasies on the ultimate trip through Tuscany. With five days dedicated entirely to pedaling through vineyard-covered hillsides and to quaint perched villages, 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.

Why you'll love it

• Pedal through Val d’Orcia’s wine country en route to a pasta factory for a tour and lunch
• Conquer steep hills and descents on a scenic loop to Montalcino
• Dine like a king or queen at a castle dinner and wine tasting in the Chianti region
• Bike to Radda in Chianti, heart of the renowned Chianti Classico wine zone
• Savor local cuisine at dinner in hilltop San Gimignano, where medieval meets magical
• Tackle a challenging ride to the walled town of Monteriggioni