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. Venice to the Dolomites

Just because you’re in the Dolomites, it doesn’t mean the cycling always needs to be hilly. The Drava Cycle Path runs alongside the Drava River and you can cycle it between South Tyrol in Italy and East Tyrol in Austria – the path even continues on to Slovenia. Our Venice to Dolomites cycle holiday stays for two nights in Venice before transferring you for point-to-point cycle rides between Cortina, Dobbiaco, Brunico and Bressanone. Follow river valleys and railway lines, and enjoy peaky views all around.

Our top selling trip: Venice to the Dolomites cycling holiday
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

The Costa Smeralda on Sardinia is a favoured haunt of royalty, a-listers and luxury yachters, but why let them have all the fun? This tailor made cycling holiday weaves inland and along the coast through some simply gorgeous scenery, exploring San Pantaleo, Gallura and also the small islands of Maddalena and Caprera. Opt for an ebike if you like, and be sure to pack a swimsuit.

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

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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. Pisa to Florence, Tuscany

Slow travel has its roots in Italy, which is why there’s no finer way to enjoy the country’s charms than on a self-guided cycling holiday, allowing you to set your own pace. Cycle from Pisa to Florence over eight days – and you can choose the longer or shorter route each day, depending on your mood. Whichever you choose, you’ll follow quiet, undulating roads past olive groves, vineyards and historic towns and villages.

Our top selling trip: Pisa to Florence cycling holiday
Read more: Slow travel in Italy

9. Tuscany

Cycling holidays in Tuscany never go out of fashion and they offer a richly rewarding alternative to wrestling crowds and coaches in Florence and Siena during the summer months. Enjoy unhurried cycling on quiet country roads between Renaissance hill towns, with opportunities to fill your saddle bags with everything from pecorino cheese to olive oil, truffles and wine as you go.

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

10. 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.
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]