June 1 - Welcome to Tuscany! Following our meeting at the Amerigo Vespucci International Airport at 12 noon, we'll meet you and transfer you to the village of Castellina-in-Chianti and our deluxe hotel in the historical center where you'll stay for the next 3 nights. Upon arrival, our mechanics will build up your bike for you before going on an easy spin this afternoon through the Chianti vineyards. This evening, we'll enjoy a "Welcome Cocktail and Dinner" in town.

June 2 - San Gimignano and Volterra Loop. Following a hearty breakfast, today's ride will take you back in time as we ride through the Classico Chianti landscape to the village of San Gimignano. Enjoy lunch in town amidst the ancient towers before riding back to the hotel or choose the option to Volterra. Relax in the pool this afternoon before a dinner of homemade ravioli, bruschetta, tiramisu and a glass of the local Chianti!

June 3 - Chianti Classico Loop / Dinner in Siena. Our ride for today is entirely centered in the Chianti Classico region! We'll pedal through the world-class vineyards and olive groves and explore such villages as Radda-in-Chianti and Greve-in-Chianti where we'll stop to sample some of the local vintages. This evening, explore lively Siena for dinner and savor some gelato in the Piazza del Campo!

June 4- Castellina-in-Chianti to Castiglione d'Orcia. The landscape changes dramatically today! Today we will ride out of the Chianti Classico through the stark Crete Senesi! This serpentine ride on cypress-lined roads through the rolling hills, wheat fields, and hilltop villas is one of Tuscany's true gems! Following lunch, we'll continue into the Val d'Orcia and our 3-star hotel in the village of Castiglione d'Orcia.

June 5- Val d'Orcia Loop. Today's ride features some of Tuscany's most photographed landscapes and villages as we ride through the Val d'Orcia, a UNESCO World Heritage Site. Have fun exploring hilltop villages such as Montalcino and Pienza as well as the ancient hot baths at Bagno Vignoni. This is truly Tuscany at it's finest! We'll celebrate the week and "all things Tuscan" this evening during our group "Farewell Dinner."

June 6- Morning ride into Siena / Transfer to Florence. Following breakfast, we'll transfer to the village of Asciano to begin your final ride to medieval Siena. After a final celebration and group cappuccinos, we'll repack bikes and transfer you to Florence's Amerigo Vespucci Airport for your return flight home or rental car pickup with the memories of having truly ridden Tuscany!