This particular biking vacation in Italy is a fixed location cycle tour based just outside San Gimignano in a wonderful Tuscan farmhouse and estate. San Gimignano is a treasure on the hill and jewel of Tuscany, wonderful for cycling and exploring. With its thirteen outstanding medieval towers, it is clear why the town is on the UNESCO world heritage list. On this cycling holiday, you will ride over clouds of sunflower fields under the Tuscan sun and along cypress-lined country roads through olive groves and vineyards, which produce some of the world’s finest olive oil and wine. You shall savour the flavour of these ingredients in the outstanding local cuisine. Travel to Etruscan and Roman times, from one picturesque hilltop to the next, each with its own history and charisma. Get pinched, this is the real thing.
The rides are along well-asphalted country lanes, secondary roads with little traffic, and 1/3 of the time on good dirt roads. Near larger towns, the roads are busier which is unavoidable.
You stay in a family-run accommodation located 5km from San Gimignano, it is a wine and oil-producing Tuscan farmhouse. It is situated around 5km from the medieval town of San Gimignano.
It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.
The 4-night program includes day 1, 2, 4, and 6 of the 7-night program
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, the 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.
This day offers a lovely circle tour around the highest hill in the immediate area, Poggio del Comune. Pedal along country lanes to Castel San Gimignano where we recommend a stop at the local bar for a delicious sandwich (panino). Continue through a nature reserve of woods and cow pastures as you return to San Gimignano for a glimmering ride and a refreshing drink.
Today you choose the ride that suits you best. 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.
Today, 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 marvelling at the magnificent palaces, churches and squares. Alternatively, visit the Duomo, the Ponte Vecchio (OldBridge) and experience the unforgettable Renaissance splendour of Florence.
Transfer to the magic and mysterious Ancient Etruscan city of Volterra, where you can explore its Alabaster artisan shops, Roman Theatre, 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.
The romantic landscape between Castel San Gimignano and Casole d’Elsa is mostly open pasture used for sheep grazing and wheat cultivating. The essence of the Montagnola area shall captivate you with its quiet, peaceful countryside. Cross kilometres of beautiful rolling green hills and marvel at the small local churches and quintessential Tuscan farmhouses.
Depart after breakfast.
To Pisa/Florence airport and the by train to Siena and then by bus or by bus from Florence direct to San Gimignano. From San Gimignano short taxi ride to accommodation.