Cycling holidays in Italy will place you in some of the country’s best loved regions where ancient towns and agricultural landscapes can be appreciated on two wheels as well as on foot. Choosing a tour should suit your cultural and gastronomic expectations as well as your fitness levels; there’s no point undertaking a challenging tour of the South Tyrolean Alps if you’d far prefer a pootle past the sunflowers and vineyards of Umbria and Tuscany. Are you looking for a leisurely break by bike or a testing experience over tough ascents? Do you want a small group guided tour or would you prefer to pedal independently on a tailor made holiday? Both options will include luggage transfers if you’re cycling from place to place, as well as road transfers to the start of trails, so you can make the most of those all-important views as soon as you start to cycle. The best advice is to be honest with yourself and your tour company when it comes to choosing the right route for you. Below are just some of the types of cycling holidays in Italy that we offer.
Easy cycling

Easy cycling

Packing a Pecorino picnic in your panniers is what makes pedalling in Italy an absolute pleasure. Our easy, introductory cycling holidays will take you over smooth tarmac roads with just a few undulations to ensure you get to enjoy views from the top of a hillside, but without getting too out of puff. Puglia is particularly easygoing, as are some sections of Tuscany, Umbria and even the Dolomites, especially around the lakes. Be honest with yourself: if you’re looking for lazy lunches, afternoons by the beach, or lay-ins after vineyard afternoons - choose an introductory itinerary with distances and gradients to suit.
Moderate cycling

Moderate cycling

There are plenty of cycling holidays in Italy that require a moderate level of fitness. Be honest about what you can cope with and don’t opt for a trip with long daily distances (50km) or Tyrolean mountain ascents unless you’re willing and fit enough to push muscles and mind that little bit more strenuously. Moderate cycling tours in Italy are for those who like a challenge, but don’t want to go too far over the top. The route from the South Tyrolean town of Bolzano to the canals of Venice, for instance, includes several challenging climbs around the Berici Hills as well as flat routes along the Bacchiglione River en route to Padova. Just make sure you’re ready for a bit more than a pootle through the park.
Challenging cycling

Challenging cycling

Lombardy, in particular, has lots of lovely ups and downs with iconic climbs on Monte Baldo and Monte Grappa just as challenging as the not so well known ascents over the hillsides of Padova and Vicenza. A challenging cycling tour in Italy is for those who want to tackle the Madonna del Ghisallo and the Muro di Sormano - where metres above sea level are marked on the road and the sweat of contestants in the Giro di Lombardia has been burned into the tarmac.

Our top Italy cycling Holiday

Matera to Puglia cycle in Italy

Matera to Puglia cycle in Italy

Nestled between the Adriatic and Ionian seas

From £1899 to £1999 8 days inc UK flights
Small group travel:
2022: 3 Apr, 10 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep
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.
Point to point or centre

Point to point or centre based

Our cycling holidays in Italy can either be undertaken as part of a small group or on a tailor made and self guided basis. Both options use locally owned accommodation, and the next day’s route will begin from the guesthouse front door or after a short road transfer to the trailhead.

Point to point cycling holidays involve cycling from one place to the next so you’ll be unpacking and packing, but getting to experience different places. Luggage will be transferred for you, so don’t worry about stuffing it all into your panniers. Popular point to point cycling routes include Cabras to Cagliari along the Costa Verde in Sardinia, and Cilento to Minori along the Amalfi Coast.
Centre based cycling holidays in Italy allow you to settle into a hotel or guesthouse and undertake circular routes or trails close to your accommodation. These sorts of trips can be really relaxing and allow you to get comfortable in one place as well as having the chance to duck out of a day’s activities if you just fancy a rest by the pool. Villabassa and Lake Como in the Lombardy region make for great bases if you’ve got plans to cycle in the Dolomites. Surrounded by both flat lakeside trails and challenging climbs, these locations offer great adventures for any cyclist looking to get unpacked, get orientated and wake up in the same bed each morning.
History, culture & food

Historical, cultural & foodie cycling holidays

Southeast Sicily sings to cyclists seeking the ancient sites of Syracuse as well as Baroque beauty in the towns of Ragusa Ibla and Modica. Opt for a cycling tour in Tuscany and no end of walled hilltop towns and medieval heritage comes to the fore, with the undulating route from Pisa to Florence littered with cultural delights amongst swathes of sunflowers and crumbling farmsteads. Abruzzo offers a feast of locally caught and cooked culinary delights to complement easy going itineraries. Think: olive oil tasting, Chieti wine paths and hearty homemade evening meals. Any cycling tour in Italy will place you in close proximity to no end of vintage villages, verdant vineyards and world famous towns; it’s up to you to decide how much time to spend in the saddle, and how much strolling over cobbled piazzas and tucking into tasty treats

Are friends electric?

Lots of our small group and tailor made cycling holidays in Italy allow you to hire an electric bike in place of a regular push bike. If you’ve never tried an electric bicycle before then do consider giving it a go. They are really easy to get the hang of, and take a fair amount of effort out of an uphill climb. It’s a bit like getting an extra push. You still use your leg muscles but you also get to enjoy the scenery and not feel too out of puff at the end, when you’re enjoying a coffee and cornetti at a cafe. For more details, see our electric bikes travel guide.
Written by Chris Owen
Photo credits: [Page banner: ickick] [Intro: Matt Watkins] [Easy cycling: Michela Simoncini] [Moderate cycling: Winniepix] [Challenging cycling: Sjaak Kempe] [Point to point or centre based 1: John Spooner] [Point to point or centre based 2: Michael Costa] [Historical, cultural & foodie : .sighele] [Are friends electric?: Ciclismo Italia]