Pedalling through the Italian region of Tuscany is a great way to get a feel for the countryside.

It’s a hilly region so don’t expect an easy ride but your efforts will be rewarded with stunning views, from green hills broken up by vineyards and olive groves, to tilled fields topped off with a lone farmhouse or line of Cyprus trees. And then there’s the Tuscan wine.

Where to go in Tuscany


The oval-shaped Piazza del Campo has to be one of the most spectacular public spaces you’ll come across. Sip an espresso at a ring-side bar or join the masses reclining on the warm red bricks of the square’s oval centre. For more information read our feature on Siena

San Gimignano

Dump your bike and climb to the hilltop town’s old fortress. From the ramparts the towers and terracotta roofs of the medieval town peter out to a crumpled blanket of countryside, dotted with buildings and patched with neat vineyards.


This pretty lookout post was built to alert Siena to war-mongering Florentines. These days it’s much more relaxed – grab an ice cream and enjoy people watching on the main piazza.


One of the best-looking towns in Tuscany – and competition is stiff. After checking out the grand castle, crest-studded tower and medieval streets, duck into the Enoteca Osteria Osticcio near the Piazza del Popolo, to sample area’s famous Brunello.


This is a key wine town in the Tuscan area of Chianti – where Chianti Classico is made. At Le Cantine, the biggest enoteca in Chianti, you can learn the differences between Classico wines and the more experimental Super Tuscans, as well as being introduced to the “King of Tuscan wines”, Brunello di Montalcino.

How to get to Tuscany

The nearest cheap flight hub is Pisa, but it’s also worth checking flights to Florence. Chain Gang (+44(0)1392 66 22 62; run six-day cycling tours of Tuscany from May to October. If a cycle tour doesn’t appeal consider basing yourself in Florence or Siena and hiring bikes for a day or two to explore the nearby countryside.

What to take

You’ll need panniers, a helmet and, perhaps most importantly, a gel seats. If you’re on a cycling tour these may be provided but it’s worth checking.