Cycling Tuscany: Chianti & Siena

Your Tuscan cycling adventure begins in the village of Poggibonsi, in the heart of Tuscany's rolling landscape. Relax and unwind at your villa; take a tip in the pool, wander around the exquisite gardens, enjoy a glass of wine on the panoramic terrace, or perhaps take a stroll around the picture-postcard Tuscan countryside.

After arrivng you’ll be met by one of our local representative's for a welcome breifing and bike fitting (the latter only if you opted for bike rental).

Following a breakfast, depart on a loop ride from heading towards the classic fortified town of Monteriggioni, its distinctive round shape dominates the surrounding Sienese plain. Continue to Colle Val d’Elsa, home to glass-blowing artisans, and perhaps visit one of the workshops.

Make sure to allow plenty of time for exploring the hilltop UNESCO Heritage Site of San Gimignano town, with its many towers. After your fill of the town head back to your countryside villa for a relaxing evening. 

Ascent/descent: 558m / 558m (1830 ft / 1830 ft)

Cycle Chianti’s winding roads through a landscape of verdant vineyards with superb wineries to the beautiful city of Siena. On reaching the cobbled streets of Siena, why not treat yourselves to a well-deserved gelato on one of Italy’s most famous squares—the Piazza del Campo? It is here in the shell-shaped town square that the famous Palio horse race is held twice a year.

Siena is a UNESCO World Heritage site and one of Italy’s must-see attractions. The city is well-known for its wine, Tuscan cuisine, art, museums and medieval Duomo architecture—soak up the atmosphere and revel in the ambience.

Ascent/descent: 408m / 261m (1338 ft / 856 ft)

Alternative longer route is 50km (31 miles) - ascent/descent: 733m / 586m (2404 ft / 1922 ft)

Today the landscape changes from vineyards to the linear cypress-crested hills near Buonconvento of the ‘Crete’. Ride through the little village of Murlo en route to your traditional accommodation. The ‘Crete Senesi’ consists of a range of hills, woods and villages; the literal translation is ‘Senese clays’. Their grey colour gives the landscape an almost lunar air.

The region is known for its black and white truffles and hosts a festival celebrating this rare and delicious delicacy.

Ascent/descent: 576m / 659m (1889 ft / 2162 ft)

Begin with the most challenging ride of the trip as you head for the tranquil red brick Benedictine monastery of Monte Oliveto Maggiore, dating from 1313. Complete with drawbridge, cyprus-lined alley and botanical medicine gardens it will no doubt prove to be another highlight of your trip.

Cycle on to your hotel in Montalcino, the winelands of the delicious Brunello red. Almost unknown until 20 years ago, Brunello di Montalcino is now one of the most famous Italian wines. We recommend trying a glass (or two!). 

Ascent/descent: 597m / 235m (1958 ft / 771 ft)

Enjoy an easier ride today as you descend to the peaceful Abbey of Sant’ Antimo, with luck, you may be able to hear the monk's Gregorian chanting.  In its hey-day, the abbey had authority over 38 churches from Pisa to Grosseto and control of around a thousand farm estates throughout Tuscany. The area is also known for its Chiusure artichokes and Montalcino honey as well as a unique grappa from the Brunello grapes and a special type of pecorino cheese. Tuck in!

Ascent/descent: 408m / 408m (1338 ft / 1338 ft) 

Alternative longer route is 50km (31 miles) - ascent/descent: 1000m / 1000m (3280 ft / 3280 ft)

Cycle through Val d’ Orcadia National Park, where you’ll find  the hilltop town of Bagno Vignoni dominated by a piazza complete with a large thermal bath, drawn from a volcanic aquifer. From here, continue to the renaissance town of Pienza, village of Montichello, before arriving at the famous wine producing town of Montepulciano for your final overnight. 

Ascent/descent: 858m / 831m (2815 ft / 2726 ft)

After a delicous breakfast you’ll be transferred to Chiusi train station, for your onward journey. If you'd like to extend your stay in Tuscany you can check out other cycling or walking holidays in the region.