Top 10 cycling holidays in Italy

No matter whether you’re looking for a self guided cycling tour or you’d prefer to follow a leader as part of a small group, there’s something about cycling holidays in Italy that never fail to help travellers slip into gear (although Lycra is completely optional). From food and wine trails in Abruzzo and Treviso, to Renaissance roads in Tuscany, and coastal tracks around Puglia, our top 10 cycling holidays allow cyclists to find their pedalling pace as well as their very own piece of la dolce vita.

1. Trieste to Pula

Starting at the top of the Istrian Peninsula, in Italy, and cycling south through Slovenia and into Croatia, this route is perfect for pedalling past vineyards, olive groves and Venetian properties. Daily distances of 35-55km encourage exercise at a relaxed pace with the disused Parenzana rail road route leading to 33 Istrian towns and cities where guest houses and home cooked meals await.
Our top selling trip: Trieste to Pula, self guided
Read more: Italy cycling guide

2. Dolomites to Venice

Cycling from the South Tyrolean town of Bolzano really sets the scene for this route to Venice, with Lake Garda, Verona and Padua all appearing along the way. Average daily distances of 50km provide a moderate challenge, whilst undulations in the Monti Berici region and flat towpath trails along the Bacchiglione River paint a picture of green countryside, fruit orchards and Palladian villas.

Our top selling trip: Cycling tour of Dolomites, Lake Garda & Venice
Read more: Dolomites travel guide

3. Matera to Lecce, Puglia

Puglia is perfect for peaceful pedalling with gently undulating Apulian hills leading to medieval villages and Ionian seaside towns, such as Gallipoli. Matera, the 2019 European capital of culture, makes an ideal place to start before you head to Alberobello, Ostuni and Otranto, via the vineyards, olive groves and circular trulli houses to be found within the Valle d'Itria. Average distances: 60km.

Our top selling trip: Matera to Puglia cycling in Italy
Read more: Cycling holidays in Puglia

4. Sardinia

Although the hill climbs might look slightly daunting, there’s plenty of time to pause and soak up the mountainous interiors and Sardinian coastline as you cycle from the Sinis Peninsula to Cape Teulada, the island’s southernmost tip. Expect peaceful, people-free trails and empty beaches as you explore the little-visited corners of Italy's second-largest island.

5. Bologna to Parma, Emilia-Romagna

If you fancy combining your cycling with delicious dining, then head into Emilia-Romagna – Italy’s top (and undervisited) pasta making region. Gently rolling hills and old railroad trails allow an even pace for this self guided trip from Bologna to Parma... with the inclines best undertaken before wine tasting sessions. Conclude with a round trip to the hilltop Torrechiara Castle.

Our top selling trip: Self guided cycling and culinary tour in Italy
Read more: Italy cycling guide

6. Palazzolo to Syracuse, Sicily

Cycling in southeast Sicily combines Mediterranean highlands and valleys with coastal trails and marshlands - especially in Vendicari Nature Reserve - to create a fairly easy-going itinerary over 40-60km per day. From Baroque buildings in Palazzolo Acreide and Modica to the bird-filled wetlands on Capo Passero and the archaeological sites of Syracuse, cycling in Sicily is always an epic odyssey.

Our top selling trip: Sicily cycling holiday
Read more: Sicily travel guide
Travel Team
If you'd like to chat about Italy cycling or need help finding a holiday to suit you we're very happy to help.

7. Palinuro to Minori, Amalfi Coast

Although Italy’s Amalfi Coast is famed for its stunning switchbacks and dramatic descents, cycling the coast and canyon trails in Cilento National Park is often equally as exciting. Daily distances of 50km take cyclists from Casalvelino Plain and Capo Palinuro to ridge routes overlooking Sorrento and Positano, to ensure you’re left in no uncertain terms as to the area’s timeless natural beauty.

8. Poggio delle Corti to Bevagna, Umbria

If you want to cycle in Tuscany-type landscapes but without the crowds then head over to Umbria and you won’t go far wrong. This is an area that’s been left relatively untouched by tourism with easy-going, 32km, cycling routes leading between Perugia, Assisi, Bevagna and Montefalco. Ride right up to cellar doors, artists’ workshops and enjoy ample opportunities for long and lazy lunches.

Our top selling trip: Umbria self guided cycling holiday
Read more: Umbria travel guide

9. Tuscany

Cycling holidays in Tuscany never go out of fashion and despite a fair few crowds and coaches in Florence and Siena during July and August there's still plenty of time and space to enjoy the smooth rural roads over the Chianti hills. Gradual gradients lead between traditional market towns, like Greve, and revered Renaissance cities to create an unhurried ride in the Tuscan countryside.

Our top selling trip: Tuscany cycling holiday through Siena and Chianti
Read more: Tuscany travel guide

10. Classic Chianti

Yep, it’s Tuscany again. This self guided cycling holiday gives you the chance to delve into the Chianti region... which means, of course, time spent cycling the Chianti Wine Route, where you can dip into any vineyards that take your fancy. There’s no need to worry about how many bottles of Chianti Classico to bundle into your pannier, either – a collection service will whisk your purchases to your final hotel. Cypress-striped hills, bird reserves, alabaster chapels and a chance to take a break from the saddle in Florence paint the rest of the pretty picture.
Written by Chris Owen
Photo credits: [Page banner: ickick] [1. Trieste to Pula: Eugene Zhyvchik] [4. Sardinia: Leonard Cotte] [7. Palinuro to Minori, Amalfi Coast: Ihor Malytskyi] [10. Cortona circular via Assisi: silvia malatini]