Bike Tour: Tuscany: San Gimignano & Chianti - 8 days

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 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 across the Elsa and Pesa valleys.

Challenge: 4.5/5 hours, 47.3/66.7 km, 1070/1500m ascent, 985/1500m descent

 

With this trip you will become familiar with the area as you make a full circle around the Poggio del Comune hill. From San Donato you go towards Castel San Gimignano passing by an unexpected sight for this very agricultural area, it is a prison. In Castel San Gimignano there is a great little bar where you can buy very good panini (sandwiches), then on in the direction of Volterra. Once you leave the asphalt road you enter the nature reserve which is mostly woods and some cow pastures, something rare in Italy. Leaving the forest behind you, you reach San Gimignano and you cycle straight through the old town centre stopping for a refreshing drink.

Challenge: 3.5 hours, 39.3 km, 1000m ascent, 1000m descent

 

Today you choose the ride which suits you best. Transfer to Colle Val d'Elsa and cycle through the gentle, 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.

Challenge: 3 hours, 40 km, 226m ascent, 106m descent, optional extention to Castellina: 12 km, 2 hours

 

On this rest day, you can choose to visit the nearby cities of Siena or Florence, both easy to reach with public transportation. Famous for its "Palio" horse race, promenade the narrow streets of Siena marveling at the magnificent palaces, churches and squares. Alternatively, visit the Duomo, the Ponte Vecchio Bridge, and experience the unforgettable Renaissance splendor of Florence.

 

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 romantic landscape between Castel San Gimignano and Casole d'Elsa is mostly open pasture used for sheep gazing and wheat cultivating. The essence of the Montagnola area shall captivate you with its quiet, peaceful countryside. Cross kilometers of beautiful rolling green hills and marvel at the small local churches and quintessential Tuscan farmhouses.

Challenge: 2.5 hours, 28 km, 532m ascent, 554m descent

 

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