Cycling, Road Cycling

Cycle of the Week: Road Cycling – Florence to Siena

20 Oct , 2016  

When in Tuscany there are a few things that you are guaranteed to see whilst peddling along; an Italian pensioner sitting at the side of the road with an espresso (or a vino) watching the world go by, one of those three-wheeled Ape Piaggios, and quite a few road cyclists. Road cycling has long been a popular past-time in Italy. This is partly due to the dry weather and dramatic roads but also because it was Italian companies that were at the heart of much of the technological innovation in racing bikes throughout the 20th Century, think Colnago, Bianchi, and De Rosa. This week we look at a trip that is steeped in road cycling heritage, a 5 day trip from Florence to Siena

Caffè e Pasticcini

Caffè e Cornetto

In a nutshell:

Where is it?

Starting in Florence with a dose of renaissance era architecture and history you will go on to ride through the heart of Tuscany’s Chianti region along stereotypical, Cyprus tree-lined roads as you wind your way south to Siena. Besides cycling along sections of the Giro d’Italia you will spend a few days in Radda, the capital of the Chianti wine region where you will have more than a few chances to quench your thirst.


170 km


Moderate to strenuous. The 170 km total distance is split over 3 days of cycling on rolling hills, with each day including several short hill climbs between 5 – 8km with a maximum gradient of 12%.

The Road to Siena

The Road to Siena

Why Cycle Here?

  • Explore the historic and architecturally important city of Florence. Soak up the culture in the countless art galleries and museums and indulge yourself in the cuisine as you tread in the footsteps of the Medicis and da Vinci in the city which was the cradle of the renaissance.
  • Learn about and taste the finest of the Chianti region’s wines on a trip to the Casa del Chianti Classico, a restored convent that dates back to the 1100s,  that serves as the home to the Chianti Classico wine consortium.
  • Cycle sections of the Giro d’Italia stages before filling up on rustic regional dishes such as parpadelle pasta.

Young Vines in the Chianti Region

Planning and Preparation:

To Florence

Florence Airport is served by a limited number of scheduled and low-cost airlines and is approximately a 20 minute bus or taxi journey to Florence Central Station.

Alternatively a direct train from Bologna Central will pull in to Florence Central Station within 45 minutes. Bologna Airport is well served by a number of low-cost airlines, a shuttle-bus from the terminal to the train station takes 20 minutes.

Flying into Pisa is another option, and is within an hours train journey of Florence.

From Siena 

Siena does not have an airport but is on a main train line and has a number of daily services to the following cities:

Pisa, 1hr 45min journey time. Daily services, up to 2 per hour.

Florence, 1-2 hours journey time. Daily services, up to 2 per hour.

Rome, 3.5 hours journey time. Daily services up to 5-6 per hour.

For more information on train times and tickets visit The Trainline Europe or the trenitalia website.

If you have any queries about the cycling tours we offer, whether they be road cycling, mountain biking or leisure cycling then do not hesitate to get in touch with a member of the team on [email protected]

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Having graduated in 2015 I joined the team here at Macs Adventure in May 2016. I split my time between spreading the word about our range of fantastic walking and cycling tours, building my knowledge of digital marketing and deciding where to travel next...