You move on between hotels every two days, and we transport your bags, so on our cycling holidays in Italy you don't need to carry a lot in your panniers and you're free to explore Italy. In-between days are a great opportunity for some local exploring, using our detailed maps and route notes as your guide while you are cycling in Italy on the quiet backroads. We've a wide range of cycling holidays in Italy - from easy, flat cycling through the Ventian vineyards, to an exhilarating tour of Chianti. Or perhaps you'd prefer a relaxing coastal route exploring the delights of Sicily? To find out more about any cycling holiday in Italy, simply follow the links below.
For full holiday details click on the appropriate cycling holiday. Italy offers a great selection of activity holidays, take a look at our activities section for further information or visit our cycling holidays section to find out how cycling in Italy with Headwater works.
Sort by:
Secrets of San Gimignano Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | Upper 2 bikes
This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panormic pools - views extend as far as Corsica on a clear day!
Departures: JFMAMJJASOND
Aspects of Assisi Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | Lower 2 bikes
This 8-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include mediaeval Bevagna, Etruscan Perugia, picture-postcard Spello and ancient Assisi.
Departures: JFMAMJJASOND
Contrasts of Puglia Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | 2 bikes
Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello and whitewashed Ostuni.
Departures: JFMAMJJASOND
Cycling in Emilia Romagna
From Please call
Cycling holiday in Italy | Hotel-to-hotel | Upper 1 bike
One of the flattest cycling routes in our programme, this is a great holiday for older couples or first timers. Highlights include gorgeous Comacchio, historic Ravenna and the splendid Renaisance city of Ferrara.
Departures: JFMAMJJASOND
Gastronomic Barolo Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | 2 bikes
Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night cycling holiday! The cycling takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.
Departures: JFMAMJJASOND
Heart of Venetia Cycling
From Please call
Cycling holiday in Italy | Single centre | Choose 1 or 2 bikes
This single centre cycling holiday is a perfect choice for people wanting a genuine grass-roots Italian experience. You'll stay on a family-run farm, in the heart of the Venetian countryside, with private pool and vineyards. Venice, Verona and Padua are all possible day trips.
Departures: JFMAMJJASOND
Secrets of Sicily Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | 2 bikes
This 8-night cycling route explores Sicily's unspoilt western coast, a sun-drenched landscape of golden bays, azure waters, swaying vines and tiny farming hamlets unchanged over the years. Lots of historic interest too: mediaeval Erice, ancient Segesta and sea-facing Marsala.
Departures: JFMAMJJASOND
Villas and Vineyards Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | 1 bike
Wonderfully flat hotel-to-hotel cycling route exploring the pretty villages, villas and castles of the Venetian countryside. Lots of historic interest and great regional cooking! A day trip to Venice is a 'must' with Padua and Vicenza also within reach.
