San Gimignano Short Break Cycling Tour Map and Itinerary

Code: CItSSG2

5 Days & 4 Nights

Discover the best of San Gimignano and Chianti on two wheels

Daily Itinerary

Day 1: Arrive in San Gimignano
We recommend flying to Rome, Florence, Pisa, Perugia or Bologna airports. Connections are possible by bus and train to San Gimignano.
After arriving at your comfortable Tuscan farmhouse near San Gimignano unwind, breathe in the wonderful country air and explore the tiny medieval village of San Donato. Take a stroll in the Tuscan hills or perhaps just relax and soak up the warm sunshine.
Overnight: San Donato de San Gimignano
You will be staying at Fattoria Voltrona for the duration of your trip. A wonderful Tuscan wine and olive oil producing estate in San Donato, which is less than five kilometres outside San Gimignano.
The accommodation is comfortable Tuscan style. All rooms are ensuite, the restaurant specialises in authentic home cooked Tuscan cuisine and the swimming pools has views to die for. You will experience the real Tuscan way of life on a family farm, surrounded by the tranquil Tuscan countryside.
Website: Fattoria Voltrona

DAY 2 Cycling in Chianti
A day of tough choices as you have to decide which ride through the perfect countryside of Chianti suits you best. Perhaps something that is best done over a freshly brewed cappuccino?
Decision made, we will transfer you to Colle Val d’Elsan where your ride begins. Cycle through the undulating hills of the Val d’ Elsa to the perfectly preserved medieval hamlet of Monteriggioni. A great spot for a coffee, chat and relax in the sun.
Continue uphill, past endless rows of vines, tranquil woods and towards Lilliano or up to Castellina in Chainti, where the view seems to encompass the whole of Chianti.
Your ride continues to Colle Val d’Elsa, where our driver will meet you to whisk you back to your hotel.
Ride: 40 Km or 67 Km with extensions

DAY 3 Vineyards of Ulignano, Certaldo Alto & Barberino
Today you will cycle through impeccable vineyards towards Ulignano and the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio.
The ascent to Certaldo is by funicular or a very steep climb if you are feeling energetic. Visit the ceramic-decorated main square, marvel at the stunning churches and enjoy a drink on the piazza while you debate the extended ride to Barberino and Tavernelle in the Chianti Classico area. The panaoramic views of Chianti are worth every ounce of the extra effort!
Ride: 42 Km or 67 Km with extensions

DAY 4
Volterra to San Gimignano
We will transfer to the ancient Etruscan city of Volterra first thing. Explore its Alabaster artisan shops, Roman Theatre, palaces and Etruscan city walls.
Then hop on your bike for an exhilarating ride through a patchwork of wheat fields and Tuscan villas down to the valley.
The inevitable climb back up to San Gimignano follows. But you really can’t complain when the scenery is this good and a glass of chilled wine is waiting.

From: £405.00 Book