The Tuscan countryside is idyllic enough to inspire bursts of poetry from even the most cynical soul – but if you’re more interested in exploring it than in waxing lyrical about its numerous charms, there’s nothing better than a lengthy bike ride. Cycling is accessible for all ages, faster than hiking, and feels a lot more personal than driving. With all those undulating hills and lush vineyards, it’s no surprise that cycling is a popular sport in the region. Check out our four favourite cycle routes: not only can they help you get up close and personal with the famous scenery, they’re also easy to access from our luxurious Tuscany villa rentals.

Crete Senesi

Crete Senesi

This pastoral region is just a few miles south of bustling Siena, so it’s easily accessible for a day trip. As well as the usual olive groves and vineyards, the area specialises in growing grain, which covers the countryside in shimmering gold. There’s a good selection of biking trails, from easy going paths running past the famous travertine caves and hot springs, to more difficult routes that climb through the hills.


Villa montalcino - Villas in Tuscany - Oliver's Travels

Villa Montalcino, Tuscany – Oliver’s Travels

There’s more to this hilltop town than its fantastic wines: it also sits right in the middle of a great cycle route. Starting at the bottom of the slope, over a gradual 8km climb to Montalcino you’ll be treated to excellent views of the valley floor as well as glimpses of the town itself. After spending some time in the town itself, you’re spoiled for choice when it comes to descents, too, with roads leading to Torrenieri, Castenuovo dell’Abate, and Buonconvento. So why not unwind at our Villa Montalcino?!

Val D’Orcia

Pienza Villa - Villas in Tuscany - Oliver's Travels

Pienza Villa, Tuscany – Oliver’s Travels

This untouched region of Tuscany is famous for its breathtaking landscapes, made up of chalk plains and neatly divided fields. The winding back roads twist around hills, passing through the picturesque villages of Montisi, Trequanda, and Pienza. It’s certainly off the beaten track, and with little in the way of traffic you’re almost guaranteed a peaceful cycle wherever you are in the area. Our Pienza Villa is a great base for discovering this part of Tuscany.


More experienced cyclists looking for an adrenaline hit would do well to head over the Apuan Alps to Lucca. The landscape here is far more dramatic, with steep peaks replacing the rolling hills that Tuscany is famous for. You’re not likely to see many tourists, but don’t be surprised if you do spot some professional cyclists making the most of the challenging terrain.

Remember to plan your route before you head out in the morning, and let someone close to you know where you’re going to be. If you feel more comfortable with an experienced pro on hand, there are a number of companies in Tuscany who offer guided cycling tours.

For more properties to rent in Italy you can browse through our full collection, or just pick your favorite one from the Italian villas with private swimming pools

Photo credit: Crete Senesi image via Didier Baertschiger and Lucca image via heipei on Flickr
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