Tuscany Biking - South of Siena

You’ll quickly understand the allure of southern Tuscany as you pedal between villages so intimate, you will experience the sounds and aromas of pranzo (the midday meal) as it’s being prepared inside Italian homes. While there are plenty of hills to climb, your efforts will be well rewarded. After spinning through rolling vineyards, past undulating wheat fields and over chalky white hills by day, savor pecorino cheese, homemade pasta, fruity olive oils, celebrated Brunello di Montalcino wines and the warmth of Italian hospitality each evening.

Day 1 Cortona
Meet in Arezzo Savor a picnic lunch of typical Tuscan fare at an 18th-century villa Pedal the level terrain of the Val di Chiana, then climb to Cortona Enjoy postcard-perfect views of the valley from this historic hill town, immortalized by Frances Mayes in her novel Under the Tuscan Sun.
Hotel: 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.

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.
Hotel :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.

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.
Hotel: 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.

Activity Level Chart

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Details: Trip shown above is a Backroads Tuscany Biking - South of Siena itinerary with Premier Inn accommodations. Casual Inn accommodations also offered. All meals are included except 2 lunches and 1 dinner. Trip begins in Siena, Italy and ends in Arezzo, Italy. Tuscany biking trip departures usually run from May through October. Contact your Journeys by Ambassador consultant for details and pricing information.