Our cycling holidays in Italy

Cycling and Italy feel intrinsically linked, with so many divine landscapes made for exploring by bike from Puglia to the Dolomites, Sicily, Amalfi, Umbria and Tuscany. Guided small group trips offer a sociable and motivational atmosphere, while self-guided holidays give you the freedom to do your own thing. And relish the experience of staying in locally owned accommodations throughout, which will sometimes even offer home cookery lessons, a delicious way to explore Italian culture further still. You’ll cycle through areas that see relatively little tourism, so your stay (and healthy appetite) helps traditional communities and ways of life to survive.

Our top Cycling holidays in Italy

Verona to Venice cycling holiday in Italy

From €495
5 days ex flights
Easy cycling holiday through the best of Veneto
Tailor made

Lake Garda to Venice cycling holiday, Italy

From €795 to €940
8 days ex flights
Easy linear cycling holiday from Verona to Venice

Sicily self guided cycling holiday in Italy

From £2349 to £2629
9 days inc UK flights
A wonderful introduction to Sicily's south-east
Tailor made

Trieste to Pula cycling tour, self guided

From €960 to €1130
8 days ex flights
Self-guided cycling tours through Italy, Slovenia and Croatia

Matera to Puglia cycle in Italy

From £2099 to £2619
8 days inc UK flights
Nestled between the Adriatic and Ionian seas
Small group2024: 7 Apr, 14 Apr, 21 Apr, 28 Apr, 5 May, 12 May, 19 May, 26 May, 2 Jun, 9 Jun, 16 Jun, 23 Jun, 1 Sep, 15 Sep, 22 Sep, 6 Oct, 13 Oct, 20 Oct

Matera to Lecce cycling holiday in Italy

From €965 to €2045
8 days ex flights
Discover the jewels of Southern Italy from Matera to Lecce
Tailor made

Cilento and Amalfi Coast cycling holiday, Italy

From £2199 to £2489
8 days inc UK flights
Rocky ridges set between small picturesque inlets
Small group2024: 13 Apr, 11 May, 18 May, 15 Jun, 31 Aug, 7 Sep, 21 Sep, 5 Oct

Dolomite valley cycling holiday in Italy

From €1670 to €1870
8 days ex flights
Incredibly scenic tour through dramatic mountain landscapes
Tailor made

Florence to Pisa cycling holiday

From £1970 to £2125
8 days ex flights
Fall in love with provincial Italy on this cycling adventure
Small group2024: 27 Apr, 11 May, 25 May, 15 Jun, 29 Jun, 13 Jul, 27 Jul, 3 Aug, 17 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct

More about our cycling holidays in Italy

Self guided or small group holidays?

Cycling in Italy offers you a choice of either self guided tailor made trips where you have plenty of flexibility on your itinerary, or small group tours where you’ll be accompanied by a guide throughout. While both have their advantages, if you’re new to cycling in Italy a small group tour is a great way to try out routes with all the logistics taken care of for you, and with a supportive, sociable bunch of riders to cheer each other on. Whichever you opt for, you’ll have a wide choice of locations, and you can be confident the routes have been honed to perfection.

Amalfi Coast cycling holiday in Italy

Feted for its glitz and glamour, Italy’s Amalfi Coast also has a sterling reputation for providing cyclists with some of the most scenic coastal rides in Europe. Highlights include long, winding descents on the Strada Statale and the fishing villages and clifftop tracks of Cilento National Park. You’ll need to hold your nerve on some of the steeper sections, and July and August are best avoided if you don’t want to navigate roads cluttered with sightseeing coaches. But just a short distance from the main coastal strip you’ll find traditional life going on as it has for centuries in blissful tranquillity.

Puglia cycling holiday in Italy

The heel of Italy’s boot is flat, dry and sunny, and ideal for cyclists looking for easy-going rides amid beautiful scenery a long way from the main tourism destinations. Puglia has two coastlines – the Adriatic and the Ionian – providing plenty of spots to pull over for a dip, so bringing a swimsuit with you every day is a smart move. Late spring and early autumn are the best times of year to cycle in Puglia, while quiet roads with unchallenging gradients make this a great region to try out self guided holidays. Small, locally owned B&Bs in sleepy seaside villages welcome you every afternoon.

Sardinia cycling holiday in Italy

The windswept Costa Verde and white beaches of the Costa del Sud make Sardinia an idyllic place for cycling holidays. Two-wheel travel is the perfect way to explore the island’s natural beauty accompanied by an invigorating sea breeze. Skip the overpriced and overcrowded Costa Smeralda in favour of wetlands where flamingos strut their stuff, quiet fishing villages and pine woods populated with deer. Small group tours are led by guides as adept at stringing together Sardinia’s history through its ancient sites as they are at pointing out the best place to find seafood linguini at the end of the ride.

Dolomites cycling holidays, Italy

There are few more dramatic backdrops for Italian cycling holidays than the classic cols and alpine routes of the Dolomites. But it’s not all calf-straining climbs here; there are plenty of more leisurely routes taking you along riverside tracks, through fruit orchards and pausing at vineyards. For a cultural treat, consider a trip that descends from the Dolomites to Lake Garda, and then to Verona and Venice. Or a centre-based tour on purpose-built cycling roads, quiet lanes and old railway tracks through illuminated tunnels – and with a spa hotel waiting for you on your return.
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.
[Self guided or small group holidays?: TRAILSOURCE.COM] [Amalfi Coast: Sander Crombach] [Puglia: Don Heffernan] [Sardinia: Exodus Travel] [Dolomites: TRAILSOURCE.COM]
Photo credits: [Page banner: ikick] [Culture : Giuseppe Milo] [Walking : Berthold Werner] [Cycling : Lucio De Marcellis] [Family holidays : fhwrdh] [Where to go in Italy : Glen MacLarty] [Types of holidays : Guldem Ustun]