Arrive at the farmhouse near San Gimignano and unwind, as this shall be your comfortable Tuscan home for the next week. Breathe in the wonderful country air as you explore the tiny medieval village of San Donato and take a stroll along the classic green rolling hills, marvelling at the breathtaking views of the surrounding countryside. Immerse yourself in tranquility.

Today you choose the ride that suits you best. 

A morning transfer takes you 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: 3 hours, 40 km, 226m ascent, 106m descent, optional extention to Castellina 12 km, 2 hours

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: 4.5 hours, 47.3 km, 1070m ascent, 985m descent, optional extention to Barberino 19km 1 hour

Transfer to the magical and mysterious Ancient Etruscan city of Volterra, where you can explore its alabaster artisanry shops, Roman theater, superb palaces and alluring city walls. Then hop on your bike for an exhilarating downhill ride into the valley, through a patchwork of wheat fields and impressive villas, followed by a delightful ascent to return to San Gimignano.

Challenge: 3.5 hours, 43.5 km, 882m ascent, 1127m descent

The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.