Itinerary

Day 1 | Arrival Day

We'll meet you at Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). Your charming hotel overlooks the val d'orcia. Pienza is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II and today is memorable not only for its architectural purity but also for its exquisite food shops. As you stroll through the pristine streets, you might decide to stock up on truffle-flavoured cheese, wild herbs or other delicacies to take home or to use for an informal dinner with a bottle of Chianti wine. Or maybe you'd rather reward yourself with some ice cream at our favorite gelateria. Dinner on your own. Some foods to try in Italy.

Day 2 | Ride Day

Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town. Overnight at the same hotel; dinner on your own again. Level: Moderate to easy Distance: 50 km. (Breakfast included)

Day 3 | Ride Day

Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked, then reward yourself with dinner at our favourite wine cellar. Accommodations are at a panoramic three-star hotel. Dinner on your own. Level: Moderate to strenuous. Distance: 46 km. (B)

Day 4 | Ride Day

Ride from Montalcino to Siena. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Late afternoon arrival in Siena. You will stay in a historic four-star hotel right in the center of town. Dinner on your own. Level: Moderate to strenuous Distance: 60 km. (B)

Day 5 | Departure Day

Departure after breakfast, at your leisure. If you want to go on to Florence, we can arrange transportation and hotels. Trains, car rentals can be arranged as well additional stays throughout Italy. (B)

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