TUSCANY

San Gimignano Loop – 84 km – 1 670 m D+

This 84 km loop around San Gimignano takes you along peaceful country roads and through classic Tuscan landscapes of vineyards and olive groves. With 1,700 meters of climbing, the ride offers a perfect mix of rolling hills and steady ascents. Expect stunning views of the medieval towers of San Gimignano along the way.

Hotel: Pescille***

San Gimignano Loop – 90 km – 1 500 m D+

A beautiful 90 km loop that explores the lesser-known backroads around San Gimignano. The climbs are steady and rewarding, leading through quiet valleys and small hilltop villages. With about 1,500 meters of elevation gain, it’s a perfect route for riders who enjoy a balanced day of challenge and scenery.

Hotel: Pescille***

San Gimignano – Pienza – 110 km – 1 900m D+

This 110 km ride links two of Tuscany’s most iconic towns, from San Gimignano to Pienza. Expect long climbs, fast descents, and breathtaking views as the landscape shifts from Chianti vineyards to the open hills of southern Tuscany. A memorable ride that captures the very best of the region.

Hotel: La Douce Montagne***

Pienza – Castellina in Chianti – 83 km – 1 550m D+

Today’s ride takes you from the stunning Renaissance town of Pienza to the heart of Chianti. Leaving the rolling hills of the Val d’Orcia, you’ll ride through one of Tuscany’s most iconic landscapes — cypress-lined roads, vineyards, and golden fields.
The route heads north through charming villages such as Buonconvento and Radda in Chianti, before reaching Castellina in Chianti, your base for the next few nights.

Hotel: Le Vauban***

Loop around Castellina in Chianti – 103 km – 1 500m D+

Your first loop ride from Castellina in Chianti takes you deep into the Chianti Classico region, surrounded by vineyards, olive groves, and medieval stone villages. You’ll pass through places like Greve in Chianti and Radda, perfect spots for a coffee or gelato stop.
The climbs are steady and scenic, offering magnificent views across the Tuscan hills.
A smooth and joyful day on the bike in the very heart of Chianti.

Hotel: Azteca***

Loop around Castellina in Chianti – 100 km – 2 100m D

Your final ride in Tuscany is a true highlight — a challenging and unforgettable loop around Chianti. You’ll follow quiet country roads through Gaiole in Chianti, San Gusmè, and Castelnuovo Berardenga, surrounded by endless vineyards and panoramic views.
The climbs are longer and tougher today, but every effort is rewarded by breathtaking scenery and peaceful roads.
A perfect way to end your week celebrating the essence of cycling in Tuscany.

Hotel : Villa Victoria****