Trip Highlights

Live a magical week in the heart of Tuscany! This year's exciting route will have you cycling along sun-drenched roads bordered by the famous Chianti vineyards, sunflowers, cypress and olive trees. You’ll visit the historic medieval villages of Pienza and San Gimignano- both steeped with Renaissance art and architecture. Enjoy deluxe villa hotel accommodations for multiple nights in the hilltop walled hamlets of Volterra, Montalcino and Castellina in Chianti! Relax at night sipping the local Brunello or Chianti while dining on rounds of homemade ravioli, bruschetta and tiramisu. A truly unforgettable cycling experience awaits you! Arrive a day early and you can sightsee Lucca or stay a couple extra days at the end and visit Florence or Siena!


Daily Itinerary


June 1st: Depart the USA for Italy.

June 2nd: Welcome to Pisa! Airport pickup and check-in to our deluxe 4-star hotel. Explore the Leaning Tower before our evening "Welcome Reception & Dinner Party".

June 3rd: After a short morning van transfer, you'll start your ride just south of Pisa into groves of cypress and olive trees on your way to the hilltop walled village of Volterra! We’ll spend three nights in a deluxe Four-Star hotel that’s perched on the edge of the village with views that go forever. Savor a four-course Group Dinner tonight that includes a great local Tuscan wine, bruschetta pomodoro, homemade ravioli stuffed with basil and pecorino cheese plus tiramisu.

June 4th: Today's route is a challenging one that follows scenic little known back roads that wind their way to a finishing climb to the amazing walled town of San Gimignano. Stroll the piazza after lunch with some homemade gelato- we know the best in town. Enjoy a realxing massage at our hotel's spa before dinner tonight.

June 5th: After a tasty buffet breakfast that includes warm homemade brioches, we'll follow a ridge-ride that'll feel like "Disneyland on a Bike"- past historic villages framed with ancient olive trees and poppy fields. Savor a picnic lunch before your final push back to Volterra! After a relaxing dip in the pool you'll be ready for an evening of sightseeing, shopping and people watching in town.

June 6th: After breakfast on our hotel’s panoramic terrace, you’ll cycle into the verdant countryside on your way to the charming hilltop village of Montalcino. We'll stay two nights in a deluxe villa hotel complete with a panoramic terrace and swimming pool. Try one of the local wines during an alfresco group dinner of local specialties of Pici pasta and Tuscan bread soup.

June 7th: Enjoy a short or long loop ride into the scenic Val d'Orcia with a lunch stop in the romantic village of Pienza. Relax later in the day with a book by our hotel's pool that overlooks the picturesque valley below. Tonight you'll explore the cobblestone streets of historic wine center of Montalcino, choosing dinner at one of the many trattorias.

June 8th: Our final riding day finds us cycling through the famous Chianti wine region on our way to famous Renaissance town of Siena. After lunch we'll van transfer back to our Pisa airport hotel (or you can explore Siena or Florence for a night or two- we’ll take your bike or extra luggage back to Pisa). Optional hotel night. Hotel shuttles to the Pisa airport or train station tonight or tomorrow.