Explore Tuscany’s rich history and scenic roads on two wheels

Tuscany, Italy, is one of the country’s most beautiful regions, and there’s no better way to take it all in than on a bike. The area is rich in cultural heritage and offers some of the best cycling in the world, with scenic Tuscany road routes alongside UNESCO World Heritage towns and cities. Ride through Renaissance Florence, home to half of Italy’s most important artworks, Siena, the heart of the Strade Bianche race, and San Gimignano, with its iconic skyline of 14 medieval towers!

Explore Tuscany by bike: scenic routes and relaxing stays

Lucca, a perfectly preserved walled town in the west, is a favorite among international cyclists. The Val d’Orcia in central Tuscany features rolling hills, iconic in cinema and the epitome of classic Tuscany. The Chianti region is ideal for wine lovers. Even if you don’t drink, the vineyard views are unforgettable.

Cycling and relaxation in Tuscany: railored rours for every rider

Our Tuscany bike tours cater to your group’s needs. We typically stay in selected hotels or agriturismos in the countryside, perfect for enjoying Tuscany’s impressive road network. This cycling holiday is ideal for those who want to ride and then relax by the pool, enjoy yoga, stroll through vineyards, or have a massage. If you prefer city life, we can base the tour in a city like Lucca, offering easy access to both the hills and city attractions.

Cycling in Tuscany is a great way to get around and explore for cyclists of all levels. With its rolling hills and stunning landscapes, Tuscany has something to offer everyone. We usually host groups riding regular road bikes but have also had mixed groups with some e-bikes; for this and all special requests, make sure to add it to your inquiry and we will do our best to accommodate you.

Tuscany’s legendary cycling routes: from the giro d’Italia to epic challenges

For more experienced cyclists, Tuscany has plenty of routes that will challenge you. The hills of the region have tested the best riders for decades with stages of the Giro d’Italia, the Strade Bianche and the Eroica, a classic cycling event on vintage bicycles. The area is steeped in cycling history from the war time exploits of Gino Bartali, who carried messages hidden in his bike frame, to the more modern World Championships of 2013 from Lucca to Florence, a brutally epic race of 272.26km with the second longest winning time in history at almost seven and a half hours!

Ready to hit Tuscany road? Fill out the form below, and let’s start planning your journey on two wheels
or visit our bespoke tours page to discover how a custom tour is crafted.

Once the ride is done, there is no better destination for calorie replenishment; Italian food is the country’s most famous export and is taken very seriously. Fresh, seasonal ingredients are combined and “kilometre zero” or “farm-to-table” are unheard of concepts here simply because that’s just the way they’ve always done it. In addition to showing you the best back roads, climbs and scenic routes, an organised multi-day bike tour means that not a single meal is wasted. Our knowledge of Tuscany and the best places to eat is the second half of the Rolling Dreamers cycling experience.