Cycling holidays in Italy overview

Cycling and Italy are intrinsically linked, with a flash of green, white and red adorning apparel the world over, signifying the eternal bond between chic style and two wheels. Small group cycling lets you appreciate the social side of Italy, both in and out of the saddle. Tailor made tours offer the freedom to explore under your own steam and create unique experiences. From Venice and Turin to Puglia and Amalfi, via Tuscany and Umbria, the wine and pasta are always better in Italy, and we think the cycling is, too. Our Italy cycling holidays travel guide has more.

Our top Cycling holidays in Italy

Matera to Puglia cycle in Italy

From £1599 to £1999
8 days inc UK flights
Nestled between the Adriatic and Ionian seas
Small group2021: 29 Aug, 5 Sep, 8 Sep, 12 Sep, 15 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct, 2022: 3 Apr, 17 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

Cycling tours in Italy, Dolomites to Venice

From £1599 to £1999
8 days inc UK flights
One of Europe's unique mountain landscapes
Small group2021: 3 Jul, 18 Sep, 2 Oct, 2022: 23 Apr, 21 May, 4 Jun, 18 Jun, 2 Jul, 6 Aug, 20 Aug, 3 Sep, 17 Sep, 1 Oct

Cycling holiday across Italy, Puglia to Sorrento

From £2099
8 days inc UK flights
Ride across the boot of Italy
Small group2021: 4 Sep

Map & highlights

Cycling holidays in Italy run the length of the country and to Sardinia, where they are the best way to escape the crowds via hidden coves and forgotten communities. Steep climbs can be had in north-east Italy as the Dolomites spring up, while the rides are more sedate in Puglia, where there’s countryside and coastal scenery. Tuscany and Umbria are lined with hilly routes that offer ample opportunities to rest up with a coffee and a view. Around the Amalfi Coast you can freewheel between sleepy fishing villages, Ancient Greek settlements and beaches that invite you to take a cooling dip.
Amalfi Coast

1. Amalfi Coast

Cycle just a short distance from the curvature of the famed Amalfi Coast and you'll discover a world away from the hairpins that leave you just as exulted but without the stress. Cycling north from Capo Palinuro towards Positano, Ravello and Salerno unveils the Bay of Naples. Pedal to ancient Greek settlements and seaside villages, with steep climbs and plenty of freewheeling to the beach.
The Dolomites

2. The Dolomites

Italians are famed for drama and there’s no more dramatic stage for cyclists than the alpine routes and classic cols of the Dolomites. However, there are also some lovely leisurely rides from beautiful Bolzano where fruit orchards and vineyards run adjacent to the Adige River and tracks lead past Lake Caldaro en-route to Tyrolean treats in the traditional mountain villages of Ora, Egna and Salorno.
Puglia

3. Puglia

As the heel of booted Italy, Puglia serves cyclists with an enviable variety of countryside and coastal scenes all the way from Matera in the north to Santa Maria di Leuca in the south. Landscapes are flat, and distances are easy-going - don’t expect too many challenges. Prepare to pedal to the unique architecture of Alberobello and the ancient sites of Otranto, as well as seafood stops in Savelletri.
Sardinia

4. Sardinia

Find yourself in fishing villages and flamingo-fringed wetlands as you cycle Sardinia’s Costa Verde. Here, flat routes follow golden beaches and the foothills of the Monte Linas provide more of a challenge. Ferry rides to the islands of San Pietro and Sant' Antioco unlock further cycling secrets off the west coast of Italy, including rocky routes along headlands and sandy coves overlooking the Med.
Tuscany

5. Tuscany

Set between the Apennines and the Med, Tuscany always appeals, with the iconic sights of Pisa and the Renaissance art of Florence offering options for free days after time spent freewheeling. From the medieval ramparts of Vinci and the baths of Montecatini Terme, to Castelnuovo di Garfagnana and the Cinque Terre coast, cycling in Tuscany can be challenging but rewards are unforgettable.
Umbria

6. Umbria

Take your time on a self guided cycling holiday in Umbria or tackle the route from Florence to Rome via hilltop towns, back roads and felt-green fields. Umbria’s uncrowded undulations are ideal for cyclists with yellow seas of sunflowers and towns like Perugia, Assisi and Spoleto punctuating the journey. Discover medieval monuments, ancient basilicas and some darn fine early morning coffee.

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

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

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.

More holiday ideas

Sicily cycling holiday in Italy

From £1699 to £1999
8 days inc UK flights
Ride through Sicily's UNESCO sites of Siracusa, Noto, Modica and Ragusa
Small group2021: 4 Jul, 19 Sep, 26 Sep, 10 Oct, 17 Oct, 2022: 17 Apr, 24 Apr, 8 May, 15 May, 29 May, 5 Jun, 19 Jun, 11 Sep, 18 Sep, 25 Sep, 9 Oct, 16 Oct

Cilento and Amalfi Coast cycling holiday, Italy

From £1749 to £1999
8 days inc UK flights
Rocky ridges set between small picturesque inlets
Small group2021: 4 Sep, 11 Sep, 25 Sep, 9 Oct, 2022: 30 Apr, 14 May, 28 May, 18 Jun, 3 Sep, 10 Sep, 24 Sep, 8 Oct

Cycling holiday in the Prosecco Hills, Italy

From £1499 to £1779
8 days inc UK flights
A great variety of scenic roads and picturesque rolling hills
Small group2021: 11 Sep, 25 Sep, 2022: 14 May, 28 May, 11 Jun, 9 Jul, 10 Sep, 24 Sep

Umbria to Tuscany cycling & cooking holiday

From €1120 to €1160
6 days ex flights
Cycling and cooking holiday between Umbria and Tuscany
Small group2021: 18 May, 30 May, 13 Jun, 25 Jun, 9 Jul, 18 Jul, 27 Aug, 12 Sep, 24 Sep, 10 Oct

Dolomites cycling holiday in Italy

From £1549 to £1879
8 days inc UK flights
The Dolomites, while avoiding the need to ride up any long climbs
Small group2021: 17 Jul, 4 Sep, 11 Sep, 2022: 21 May, 11 Jun, 16 Jul, 3 Sep, 10 Sep

Puglia cycling tour

From £1749 to £1859
8 days inc UK flights
Reasonable easy cycling. Excellent bikes. Good weather.
Tailor made
Quote. The secret to a great holiday is that it's great for everyone - you, local communities and nature.
Tourist and Masai

More about Cycling holidays in Italy

Sardinia

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

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]