Tuscany Cycling Holidays

Highlights of Tuscany Bike Tours

Cycling through Tuscany is a feast for the senses – think rolling hills draped in vineyards, sun-dappled olive groves, and medieval towns perched like crown jewels on hilltops. You can ride quiet Tuscan roads or even venture out on to the legendary strade bianche, white gravel roads that wind through postcard-perfect landscapes. Enjoy stops in iconic spots in Chianti and medieval towns like Siena and San Gimignano. Each ride rewards you with sweeping views and each descent leads to a rustic trattoria serving fresh pasta and world famous wine. Enjoy the very best of cycling in Italy with a Tuscan cycling adventure.

Types of Tuscany Cycling Holidays We Offer

Whether you want the freedom to explore at your own pace or the comfort of riding with a guide, Tuscany serves up the perfect cycling escape for every kind of rider. Choose a self-guided cycling trip in Tuscany and you’ll chart your own course through rolling vineyards, olive groves, and timeless hilltop towns, with our hand-picked Tuscan routes and local know-how guiding your way. Prefer a little more support? Our Tuscany guided cycling tours are led by passionate locals who’ll show you the best views, the hidden trattorias, and exactly where to stop for that perfect glass of Chianti. Either way, we’ve got the details sorted, from luggage transfers to boutique accommodation, so you can focus on riding, relaxing and falling in love with Tuscany, one pedal stroke at a time.

Ride Amongst Olive Groves and Vineyards in Tuscany

The Chianti region is legendary and willed with world famous vineyards. Pedal the gentle, rolling lanes between Greve, Radda, Gaiole and Castellina, framed by centuries-old olive trees and vineyards. Pop into iconic estates like Castello di Brolio or Volpaia for tastings – this terrain offers a perfect blend of cultural charm and scenic riding.

Discover Tuscan Hilltop Villages

Tuscany is scattered with hilltop villages that look like they’ve leapt straight from a Renaissance painting and riding between them is like cycling through history itself. Take San Gimignano, the “medieval Manhattan” with its skyline of ancient towers and cobbled streets. The climb up is always worth it, especially with a gelato from the piazza waiting at the top.

Then there’s Siena, a true Tuscan treasure. Ride through its historic gates and into the heart of the city where the Piazza del Campo, home to the legendary Palio horse race, spills out like a stone amphitheatre. Nearby, you’ve got Pienza, Montepulciano and Montalcino, each perched above rolling vineyards and serving up jaw-dropping views, delicious local fare and a serious sense of place. These villages aren’t just pretty stops, they’re the soul of Tuscany.

Family Cycling Holidays in Tuscany

Enjoy a family cycling holiday in Tuscany by riding from Pisa to Florence. Set off from the iconic Leaning Tower in Pisa and follow gentle, well maintained paths through rolling Tuscan countryside, passing fields of sunflowers and vineyards with charming rural villages along the way. Enjoy comfortable family friendly accommodations, seamless luggage transfers and a choice of bikes including hybrids, e-bikes and children's models. Pedal at your own pace, soak up the ever changing landscapes and finish in Florence where you can explore world famous art, architecture and gelato filled streets. It’s all designed to make cycling fun, accessible and unforgettable for every generation.