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

Matera to Puglia cycle in Italy

From £1949 to £2249
8 days inc UK flights
Nestled between the Adriatic and Ionian seas
Small group2023: 2 Apr, 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct

Cilento and Amalfi Coast cycling holiday, Italy

From £1979 to £2449
8 days inc UK flights
Rocky ridges set between small picturesque inlets
Small group2023: 29 Apr, 13 May, 27 May, 17 Jun, 2 Sep, 9 Sep, 23 Sep, 7 Oct, 2024: 13 Apr, 11 May, 18 May, 15 Jun, 31 Aug, 7 Sep, 21 Sep, 5 Oct

Cycling tours in Italy, Dolomites to Venice

From £1999 to £2249
8 days inc UK flights
One of Europe's unique mountain landscapes
Small group2023: 22 Apr, 20 May, 3 Jun, 17 Jun, 1 Jul, 19 Aug, 2 Sep, 16 Sep, 30 Sep

Puglia cycling tour

From £1749
8 days inc UK flights
Reasonable easy cycling. Excellent bikes. Good weather.
Tailor made

Chianti self guided cycling holiday in Italy

From £2039
11 days inc UK flights
Pedal through the archetypal Tuscan countryside

Umbria to Tuscany cycling & cooking holiday

From €1540 to €1640
5 days ex flights
Cycling and cooking holiday between Umbria and Tuscany
Small group2023: 21 May, 28 May, 24 Sep

Trieste to Pula cycling tour, self guided

From €930 to €1090
8 days ex flights
Self-guided cycling tours through Italy, Slovenia and Croatia

Sicily cycling holiday in Italy

From £1820 to £2449
8 days inc UK flights
Ride through Sicily's UNESCO sites of Siracusa, Noto, Modica and Ragusa
Small group2023: 16 Apr, 23 Apr, 21 May, 28 May, 4 Jun, 18 Jun, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 2024: 14 Apr, 21 Apr, 5 May, 19 May, 26 May, 2 Jun, 16 Jun, 1 Sep, 8 Sep, 15 Sep, 22 Sep, 29 Sep, 6 Oct, 13 Oct

Tuscany cycling holiday through Siena & Chianti

From £2049 to £2199
8 days inc UK flights
Cycle the most evocative and romantic landscapes
Small group2023: 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 26 Aug, 9 Sep, 16 Sep, 23 Sep, 30 Sep

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]