Days 1-2 Medieval flavor and ancient traditions await in charming hilltop towns  The only hill town on the valley floor, Montefalco is a great spot for soaking up views of Assisi to the north and Spoleto in the south  Coast downhill to a bountiful picnic lunch in the heart of the Sagrantino wine (Umbria’s “big red”) production zone Dine and wander in timeless Bevagna, perhaps pausing to browse for ceramics and silver Beauty abounds in Assisi, from the stunning Basilica of Saint Francis to the verdant valley below.

Day 3 Welcome to Tuscany!  Taste splendid wines, like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano  Imagine you’re in a postcard as you pedal along a sinuous ribbon of road flanked by bright red poppies, cypress trees and undulating hills Spin through the Orcia Valley, where fortified towns and distant Mount Amiata provide a dramatic backdrop Explore Pienza, the Renaissance utopia of Pope Pius II – and birthplace of heavenly pecorino cheese  Join our friend Vittorio in his cozy cantina for a private degustazione We’re welcomed like family at La Chiusa – you’ll understand why we’ve been coming here for years!

Days 4-6 Cruise past olive groves and sunflower fields to La Braccesca wine estate for an exclusive cooking demo and lunch  Pedal through the Chiana Valley, where white Chianina cows graze Bike to historic hilltop Cortona, surrounded by 3,000-year-old Etruscan walls, and the setting for Under the Tuscan Sun Giovanni, our longtime local guide, leads us through this celebrated town  Savor a classic Tuscan tableau during an easy ride past ancient farmhouses, vast wheat fields and cypress-lined roads.

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