The very best of Tuscany can be discovered when going beyond the guidebook.

Tuscany sets the senses on fire. The word alone evokes visions of the greatest art and literature, and the tastes and smells of the most exquisite food and wines. The touch of ancient stone carved and sun-bleached into some of the most beautiful buildings, towns and cities in the world is unforgettable – and the old towns at the heart of Florence, Siena, Pisa, Pienza, San Gimignano and Montecatini Terme are all World Heritage Sites. The landscapes? Magical, like something from a storybook or a daydream. There is no better way of experiencing this enchanted place than with friends and by bike.

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. 

Viagnamaggio - Greve 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. 

Viagnamaggio - Greve in Chianti

66 KM, 1150M ELEVATION

After a leisurely morning and healthy Italian breakfast we start our ride, led by the now familiar friendly face of Alberto, who heads north east. The ride offers the chance to see up close farmers working the fields and skilled labourers tending to endless vineyards. Our coffee stop is a chance to say ‘ciao’ to our friend Monica the friendly barista (Bar Centrale) in Monteriggioni. The walled town is amongst the finiest in the whole of Italy. The ride continues towards San Gimignano and a visit to the home of Ciappi family, wine makers for over a 100 years. A rare insight awaits as they open the doors to one of the smaller wineries in Tuscany.

La Certosa di Maggiano - Siena

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

La Certosa di Maggiano - Siena

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 school 

Il Miraggio - San Quirico d’Orcia

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 - San Quirico d’Orcia

• 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.