There aren’t many better ways to see a country than by bike. Eco-friendly, fast, and able to reach those places a little further of the tourist trails, a good, old-fashioned cycling holiday led by a local means you can get further off the beaten track than ever before, and enjoy that freeing sensation of sweeping along beautiful roads to fascinating new discoveries.

And Italy is no exception to the, better explored by bike, rule. Our cycling holidays in Italy show you the very best of the landscape, the rolling hillsides and acres of vineyards in Umbria, to the offbeat rural experiences or hidden city gems in Puglia you simply wouldn’t find alone.

Cycling Adventures in Italy

Cycling holidays allow you to reach places and see sights that ordinarily would be out of reach. When you jump on a bike, there is virtually nowhere out of reach. You can make it deep into the countryside to discover unique rural experiences, you can navigate the narrow tracks or alleyways that big tour buses can’t, and you can achieve the childish sense of joy that comes from discovering new sights at every bend as the wind rushes through your hair.

In Italy, a cycling holiday isn’t just about vineyards and wineries in Tuscany (even if there are plenty about), it’s about getting right off the beaten track and discovering small villages in Umbria, about stumbling upon ancient olive groves and atmospheric, authentic fishing villages.

There are few feelings as rewarding as getting back from a long day out in the Umbrian countryside, enjoying the sweeping country roads and the beautiful hillsides, before sitting back in a beautiful walled, hilltop town, sipping a glass of local red wine as the sun goes down, or firing up a fish grill in Puglia after a day discovering the local hidden gems between the shady lemon groves and misty sea cliffs.

A cycling holiday in Italy with Not In The Guidebooks takes you directly to these authentic experiences thanks to your local guide. All our guides and hosts are passionate about showing off the best, non-touristy parts of their home, they want to show you the best trails and the best roads to cycle on, and the unique, local things to do at the end of them.

Forget planning routes and worrying that you’re missing out on the best sights and things to do, you can simply relax as you freewheel through the stunning scenery.

Where to experience cycling holidays in Italy

Head to the lesser-known neighbour of Tuscany to discover cycling holidays in Umbria that explore rolling green hillsides, shady vineyards and beautiful walled towns and villages complete with medieval churches and elegant little piazzas. One look at the eye-wateringly beautiful town of Assisi, glowing softly in the evening light, shows you exactly why there is an air of spirituality around the place, and with stunning food and wine, it’s the perfect place to pedal and soak up the special atmosphere.

Alternatively, the white-washed heel of the boot of Italy, Puglia, is a honeycomb of secret misty coves, stunning white-sand beaches, charismatic coastal towns and rugged, fascinating countryside. Getting off the beaten track here opens up the uncharted part of the region where you’ll find the most rewarding experiences and authentic sights.

Wherever you go for a cycling holiday in Italy, you can be sure that you’ll create memories of unique experiences that last a lifetime.

Who are our Italian cycling holiday guests?

People who haven’t ridden a bike since they were 12, those looking for offbeat trails and long days in the saddle, or those just looking to experience a place in a more unique way, everyone is welcome on our cycling holidays in Italy.

Your guides will be experts in judging the length and difficulty of each ride, and make sure that they take you to the very best places along safe routes, so that you can simply relax and drink in the scenery, and enjoy the sensation of sweeping through the Italian countryside.

All you need to bring is energy, a sense of curiosity and a thirst to discover something new. Sound like you?

Why choose Not In The Guidebooks?

We’re passionate about helping people find the most amazing experiences on their travels, through meeting local people, exploring new places, and discovering alternative activities that make holidays special. We do this by carefully selecting partners in countries around the world who are experts in their local area, sourcing interesting people who can guide you through immersive experiences.

We’ve got local partners all across Italy, from the rolling hills of Umbria, all the way to the pristine beaches and honeycomb caves of Puglia. Choosing a Not In The Guide Books holiday in Italy means you don’t have to choose between a beach holiday or an activity-filled break, you can get the best of both worlds with a unique trip.