Luxury Tuscany and Vineyards

Stages of your Tour

1. Welcome to tuscany ride

   25 km | 400 mt ElevAtion

   We start with a welcome ride to fire your imagination for the coming days. The roads in this part of Tuscany were ancient even before the Etruscans came to these beautiful hills. Between stone farmhouses and elegant cypress trees, we will make our way to Greve in Chianti, set on a small, fast-flowing river and host of the annual Chianti Classico wine festival and the magnificent Villa Vignamaggio, built fourteenth-century by the Gherardini family, whose cousin Mona Lisa Gherardini was later portrayed by Leonardi Da Vinci in the world’s best-known painting.

   Terre di Baccio - Greve in Chianti

2. castellina in Chianti

   55km, 1200m elevation.

   The promontories of the Chianti Hills are dotted with medieval towns still enclosed by their original 700-year-old walls. These stone military constructions somehow seem to us the most harmonious of buildings. Yet, in altogether less pacific times, the armies of warring Florence and Siena gathered here before the hostilities, and peace treaties were signed after them. After collecting our bikes, lovingly cleaned and serviced each evening by our staff, our morning coffee stop will allow us to contemplate the dreamy beauty of the Chianti Hills, the peaceful product of years of ancient strife.
   Terre di Baccio - Greve in Chianti

3. gaiole in chianti

   66 km, 1150m elevation

   From the fortified hilltop village of Radda in Chianti, we descend to gorgeous Gaiole in Chianti, home of the stunning Brolio castle and birthplace of the famous Strade Bianche race, which follows the rustic farm routes that crisscross the Tuscan panorama. Rivers too meander across the ancient battlegrounds. In his Divine Comedy, Italy’s greatest poet Dante Alighieri tells how one thirteenth-century conflict left one of the day’s rivers, the Arbia, running red with soldiers’ blood. When Siena comes into view, it is time to be overwhelmed by the medieval sublime.
   Hotel Belvedere di San Leonino - Chianti

4. San Gimignano

   70 km, 1000m elevation.

   Your Italy Bike Tours’ guides will lead you north-west from spellbinding Siena towards some of Tuscany’s most improbable attractions, like the astonishing, storybook castle of Monteriggioni where the Russell Crowe movie Gladiator was filmed – in reality, a entire fortified town that will take your breath away – or San Gimignano, where the noble families once competed among themselves to build the biggest tower. Now a UNESCO World Heritage Site, 72 towers rose above the town in the 13th century, creating  a medieval Manhattan. Fourteen of them still remain. An astonishing, unforgettable day

   Hotel Belvedere di San Leonino - Chianti

5. Buonconvento

   66 km, 950 m elevation.

   For two million years, an ocean covered the Crete Senesi, literally the ‘clays of Siena,’ so today you will trek across an ancient seabed of grey-blue clay, chalk and rock salt, which some compare to the surface of the moon. Unsurprisingly, these scenes inspired a celebrated painting tradition. Passing solitary cypresses, isolated farms and eerie, low-lying forests, you will discover one walled village after another: Asciano, purchased in the thirteenth century by Siena and surrounded by walls, and Buonconvento, whose gallery hosts the works of the famous Siena landscape.

   Il Miraggio - Val d’Orcia

6. Montalcino

   63 km, 1000 m elevation

   The stunning hillside town of San Quirico d’Orcia is mentioned in the oldest book in Western Europe, the Liber Linteus Zagrabiensis (300 BC). Monumental Montalcino, a military outpost in medieval times, was serendipitously located in a fantastically productive grape area, making it the home of two world-class wines, Brunello and Rosso di Montalcino. Yet neither is the aesthetic high point today. When you glimpse the UNESCO World Heritage Site of Pienza, at the easternmost point of the itinerary, you will know that you have at last seen perfect beauty.

    Il Miraggio - Val d’Orcia

7. ARRIVEDERCI!

   NO RIDE TODAY

   Sadly, all good things must come to an end. We will be delighted to assist you with your onward travel, or should you wish, we would be happy to arrange more days of beautiful cycling in Italy.

The perfect cycling holiday requires pedaling on the perfect bike. So should you not wish to bring your own bike with you we have a number of beautiful bikes that you can hire at very reasonable prices. If you are not sure what is the perfect bike for you then fire us an email and we will be delighted give you some expert advice. You can find more information about our bikes below. And yes you can buy our bikes if you fall in love with them!