Our first ride will immerse us in the heart and beauty of the Chianti Classico region. Pedal through gently rolling hills and breathtaking landscapes, stopping at a cozy restaurant for lunch. Challenge yourself to a longer afternoon ride, or head back to the gorgeous hotel. This evening, indulge in our first dinner together at the hotel.  

Pedal along country roads, through vineyards and silvery olive groves to a local trattoria for lunch. Tonight, we’re off to a family-run farm and winery where Marta, the owner, will host us. Pizza and samples of organic products and biodynamic wines will be service among the vineyards.  

Today’s ride is one of the most beautiful of the week-we'll pedal through the crete leading to Siena, with the option to make this a Century Ride. We’ll pedal into the villa of our old friends who will share their love-story with Tuscany over an unforgettable lunch.  

Hop on our bikes this morning and pedal through the foothills below Montepulciano with picturesque views of the temple of San Biagio in the distance. After one final hill, set off to explore Cortona’s winding streets and shops. Sit back by the pool before a relaxing evening dining at the hotel. 

Set out on a quiet ride through Umbria’s Valle del Niccone, eventually pushing back uphill for lunch in an agriturismo with our friend Francesco. Savour delicacies made with the freshest ingredients before hopping back on the bikes. This evening, we have been invited to a private tasting and dinner in one of the region’s top wineries for a perfect end to our week.