Undiscovered Umbria to Cortona, Land of the Tuscan Sun

No doubt you'll arrive with certain expectations. After all, artists and writers have waxed hyperbolic on the glories of Umbria and Tuscany for centuries - how can you not have preconceived notions? But somehow it's still a surprise, the sensory feast that surrounds you. You're still floored by the beauty of silvery olive groves and endless acres of vineyards. By springtime poppies. Summertime sunflowers. Harvest-ready grapes in the fall. By the symphony of flavors in even the simplest of dishes. And the sheer warmth and passione of the local people. Expectations exceeded? Just another day in the heart of Italy.

Days 1-2 Soak up the medieval flavor and ancient traditions of charming hilltop towns  Beneath rolling Umbrian hills, enjoy a riverside spin on the Assisi-Spoleto bike path  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 Taste splendid Umbrian wines, like full-bodied Sagrantino and Montefalco Rosso.

Day 3 Welcome to Tuscany!  Imagine you've pedaled into a postcard as you head along a sinuous ribbon of road flanked by 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 For dinner, 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 visit and picnic  Spin through the Chiana Valley, where white Chianina cows graze Pedal gentle terrain 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.