Dates, itineraries and pricing are subject to change
Sweeping vistas and gently rolling hills of the Val di Chiana greet you south of Siena - the land of celebrated Sangiovese vineyards and villages rich with Renaissance architecture. On this biking trip, we've taken our cue from the pace of Italian country life and designed an itinerary that encourages you to stop and smell the cappuccino. Pedal past springtime poppies or autumn's golden vineyards, then tackle the hills and be rewarded with gorgeous views. When you're ready to relax, let us shuttle you to such picture-perfect towns as Montepulciano, Pienza and Cortona for afternoons of leisurely exploration.
Days 1: Cortona
Day 2 - 3: Petrignano del Lago
Marvel at Cortona's majestic architecture during a walking tour with a local guide Let your wheels do the work on a downhill ride to the valley floor, followed by a leisurely spin through a classic southern Tuscan landscape of rolling fields, cypress-lined roads and quiet hamlets Bike to the atmospheric fortified town of Castiglione del Lago, set on a promontory on Lake Trasimeno in Umbria Learn the secrets of Tuscan cooking from a local expert.
Days 4 - 6: Montefollonico
No visit to southern Tuscany would be complete without seeing Montepulciano, the highest of the hill towns, filled with glorious Renaissance buildings A fourth-generation vintner invites us to his family's cantina for a tasting of Vino Nobile Ride to historic Pienza with expansive views of the Val d'Orcia Sample locally made pecorino cheese, admire exquisite ceramics and wander down medieval streets Hike in forests of oak, broom and cypress above Montefollonico.
Villa Marsili, Cortona (1 night) This elegant 14th-century palazzo rests within Cortona's Etruscan walls and offers outstanding views of the Val di Chiana.
Relais Alla Corte del Sole, Petrignano del Lago (2 nights) At this beautiful 16th-century estate, you'll find uniquely decorated guest rooms graced with rich fabrics, antiques, wood-beamed ceilings and brick floors.
Relais La Chiusa, Montefollonico (2 nights) An old stone farmhouse and olive oil mill converted into a charming country inn with an acclaimed restaurant featuring fresh homemade cuisine.
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