Arrive at the hotel in San Gimignano and unwind, as this shall be your comfortable Tuscan home for the next few days. Breathe in the wonderful country air and take a stroll along the classic green rolling hills, marvelling at the breath-taking views of the surrounding countryside. Immerse yourself in the tranquillity.

Today you will cycle through prestigious vineyards towards Ulignano and the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio. The ascent to Certaldo is either by funicular or by a very steep climb. After visiting its ceramic-decorated main square and stunning churches, you can choose an extended ride to Barberino and Tavernelle in the Chianti Classico area, offering magnificent views.

Challenge: 35/51 km, 580/970 m ascent, 580/970 m descent

This day offers a lovely loop ride around the highest hill in the surrounding area, Poggio del Comune. Before you start to pedal along country lanes we recommend you make a stop at the local bar by the Castel San Gimignano, and pick up a delicious sandwich (panino) for along the way. Continue through a nature reserve of woods and cow pastures as you return to San Gimignano for a glimmering ride and a refreshing drink

Challenge: 36.5km, 826 m ascent, 826 m descent

Morning transfer to Colle Val d’Elsa. Cycle along the undulating hills of the Val d’Elsa to the perfectly preserved medieval hamlet of Monteriggioni. Continue uphill, past abundant vineyards and stimulating woods, either towards Lilliano or directly up to Castellina in Chianti, where the views are spellbinding. Afternoon transfer from Colle Val d’Elsa back to the accommodation. 

Challenge: 40 km, 640 m ascent, 640 m descent
Optional extention to Castellina: + 14 km, 315 m ascent, 315 m descent

Today, you will leave San Gimignano behind and cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and villas, you reach the base of the imposing hill upon which the town is set. One more solid climb before you arrive at your marvellous hotel, a former convent set inside in the gates of the old city centre.

Challenge: 35.9 km, 922m ascent, 649m descent

After an exhilarating downhill ride into the valley, you cycle through the lovely Val d’Era and over stretches of ‘strade bianche’, typical Tuscan white roads. The itinerary winds through the landscape filled with remote farmsteads and villas, and hills covered with vines and olive groves. Grand views on the vast infinitely undulating terrain will accompany you throughout the entire day.

Challenge: 38.3 km, 840 m ascent, 840 m descent

An easy yet very scenic ride today in the surroundings of Volterra. Erosion caused by rain water have artistically sculpted the landscape creating cracks and gullies of a majestic beauty. After descending from Volterra you will venture off the beaten track on unpaved tracks to then return on the very panoramic Strada del Cornocchio.

Challenge: 37 km, 920 m ascent, 920 m descent

Loop ride via Lajatico & Teatro del Silenzio   

Leaving Volterra, the landscape envelops you in an expanse of green and golden hills scattered with cypresses and farmhouses, the epitome of Tuscan beauty. A short stretch on asphalt takes you to the village of Lajatico, known for being the birth place of tenor Andrea Bocelli: along your way, the stunning “Theatre of Silence”, a quaint lake adorned with pieces of contemporary art that once a year turns into an open-air amphitheater for a much awaited Bocelli concert. 

You then continue along plain cartroads and nice asphalted roads, with a final challenging uphill stretch that you can break with a visit to the Etruscan Necropolis, before cycling back to Volterra.

Challenge: 45 km, 850 m ascent, 850 m descent