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Adventure of the Week: Cycling Tuscany: Chianti and Siena
3 Min Read
14 November 2017
Adventure of the Week: Cycling Tuscany: Chianti and Siena

The very thought of Tuscany makes me happy. When I close my eyes and drift off into a Tuscan reverie, it is the feel of rough stone walls against my fingers, of feeling lightheaded from staring up at immaculately crafted towers. I can taste the rich depths of the Brunello and feel the hearty bread tear off in my hand. Tuscany, while beautiful, is not all about the external.  It is a region of passion, of enjoyment, of appreciation. There is no better way to explore this Tuscan experience than from the saddle of a bike. 

In a nutshell

Cycling Tuscany: Chianti and Siena does exactly what the name suggests. It allows you to explore the Chianti region and spend time in the glorious city of Siena. However, there is so much more to the trip than this. Distance: Each day on this trip you will cycle between 32 and 46km. There are a few days when you will take looped cycles, leaving and returning to the same point, so if you fancy exploring the town and giving the bike a rest for the day, you can certainly do this. Grade: Moderate. This being Tuscany, and there being a lot of hilltop villages, it means that there is some climbing involved in the trip. It mostly tends to be the final stretch as you climb up to your accommodation for the night, but some of the climbs can feel eternal.  However, it also means that first thing in the morning, you get to whizz down a beautiful curvaceous road to get your day started in a great way.

Winding roads in the Creti region 


Tuscany is in central Italy and this trip visits the southern part of the region, taking in some of its finest towns and cities. Starting off in the town of Poggibonsi, you cycle out and explore  Monteriggioni, and San Gimignano, before cycling south to Siena and onwards to finish in Montalcino.

Why Walk Here?

Towns! This trip takes you to some of the most mindbendingly beautiful towns and cities on the planet. These are places that I guarantee you will wander around and at least once, consider moving there. They showcase a way of life that most of us romanticise and yearn for. They are places for dreamers, places for those who take home a little of the culture to change their own day-to-day lives. First up I am going to go for the main draw, Siena. Siena is widely renowned as Italy's most beautiful medieval city. It has the world famous Il Campo Piazza, most famed for the annual Palio horse race. (see the James Bond film Quantum of Solace for more info!) The city is dominated by the Duomo, the red Palazzo Pubblico and its tower, Torre del Mangia. A perfect, and very photogenic city to visit.

When you see the 14 towers of San Gimignano appear on the horizon, you know you are cycling towards something very special. The architecture and old world feeling of the town is a joy to experience, as is the local white wine, Vernaccia di San Gimignano. Then there is the Crete region and its little medieval gem, Buonconvento. The Creti Senesi is an area in Tuscany which is unlike any other part.  Its grey, lunar landscape is a stark contrast to the rolling green hills you are used to by this point, but this is where you will snap your 'classic' Tuscany photograph. This is the land of cypress-lined roads, endless fields of crops all framed by the crumbling cliffs and grey, clay landscapes that define the region. Buonconvento has the dilapidated charm of an authentic, non-touristy medieval town. Plaster walls are cracked and trees grow from the walls, but it is a relaxing, lovely town and one of the hidden gems of Tuscany. 

San Gimignano in the distance

Then, of course, there is the food, the wine and the people. Tuscan people are endlessly friendly. Their willingness to help and insistence that you are their guest is unwavering. Add to this some of the finest wines in all of Italy (even the world, if you are willing to spend a bit extra) and rustic, honest food, all fresh, all local and just the way it should be.

Planning and preparation

You can head out to enjoy our Chianti and Siena trip anytime from March to November. Summer can be a bit warm, but the best times are from April to June, when the countryside is alive with colour. Flying to Pisa airport is the easiest way to go and from there it is only around an hour on the train to get to Poggibonsi and the start of your trip. Our team are always happy to offer advice on the ideal itinerary so please do get in touch via info@macsadventure.com.


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