Pienza, the "perfect town," is a stunning example of Renaissance-era town planning. If you have even a slight appreciation for beautiful architecture, strolling its cobblestone streets is a true delight. Gift hunters will also find plenty to explore. Pienza is also a gastronomic paradise, offering a wealth of local flavors.

A Cicloposse representative will meet you for a bike fitting and briefing, followed by a warm-up loop ride to San Quirico to test your bike and equipment. You’ll stop in the village to visit the Horti Leonini Garden, the town's top attraction.

Your charming hotel, Il Chiostro, is housed in a 15th-century convent, nestled in a quiet, secluded location in the heart of Pienza. Rebuilt between 1459 and 1462, it’s a rare masterpiece, conceived by Pope Pius II.

Total Distance: 12 mi / 20 km
Elevation gain: +928 ft / -945 ft |+283 m / -288 m
Accommodations: Hotel Relais Il Chiostro in Pienza
Meals: None

Loop ride to Montepulciano and Monticchiello. Start your day with a pleasant downhill, you’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages…Among the sites you’ll ride through meet the hilltop villages of Castelmuzio and Petroio. Today’s ride will take you to Montepulciano, which is famous for the production of Vino Nobile di Montepulciano. Visit one of the typical wine cellars in town, the oldest one in town is situated under the Ricci Palace. Back to Pienza through Monticchiello… another hilltop village.

Total Distance: 33 mi / 53 km
Elevation gain +3504 ft / -3511 ft | +1068 m / -1070 m
Accommodations: Hotel Relais Il Chiostro in Pienza
Meals: Breakfast

Today’s ride will take you to Bagno Vignoni, a thermal spa town that dates back to Roman times right before reaching the beautiful Castiglione d'Orcia. Enjoy a long downhill to the monastery of Sant'Antimo where you might catch one of several vesper services performed each day by the monks.. On your way to the Etruscan village and wine town of Montalcino, where you will stay, you’ll pedal through magnificent vineyards.

Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italian’s premier fine red wines, Brunello di Montalcino.
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.

Total Distance: 28 miles / 44 km
Elevation gain: +3021 ft / -2874 ft | +920 m / -876 m
Accommodations: Hotel Vecchia Oliviera in Montalcino
Meals: Breakfast

Ride from Montalcino to Siena. Start with 10 km descent and pass through Buonconvento. Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum. Continue to Ville di Corsano always on a breathtaking scenery and end up in Siena arch gate Porta San Marco. You'll have time to take a leisurely stroll around this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. Piazza del Campo is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.

Total distance 35 miles / 55 km
Elevation gain +2887 ft / -3531 ft | +880 m / -1076 m
Accommodations: Hotel Villa STR
Meals: Breakfast

Tour ends today in Siena after breakfast. Consider adding on a few days to explore Siena and southern Tuscany. Airport transfer also available to Florence (additional costs apply).

Meals: Breakfast