ITALY CYCLING HOLIDAYS GUIDE
Cycling and Italy are intrinsically linked, with a flash of green, white and red adorning apparel the world over to signify the eternal bond between chic style and two wheels. There’s just something about feeling the road, every lump and bump, of watching vineyards roll by, without windows, that allows you to understand what makes Italians tick. You just don’t get that in a car, or on two legs; it’s that added freedom that sets cyclists apart from the pack.
Italians get cycling, their heroes cycle, it’s in their DNA. This goes for drivers too; they’re used to seeing cyclists road training and you might even get cheered on as they pass.![]()
Cycling as part of a small group lets you appreciate the social side of Italy, both on and off the saddle. Tailor made tours offer the freedom to explore under your own steam to create unique experiences; ones that you’ll never want to forget. From Venice and Turin to Puglia and Amalfi, via Tuscany and Umbria, no matter where you are, the wine and the pasta always taste better in Italy, and we think you’ll find the cycling does, too. Read on in our Italy cycling holidays guide.
Our Italy cycling Holidays
Matera to Puglia cycle in Italy
Nestled between the Adriatic and Ionian seas
From
£1499 to £1899
8 days
inc UK flights
Cycling tours in Italy, Dolomites, Lake Garda & Venice
One of Europe's unique mountain landscapes
From
£1549 to £1899
8 days
inc UK flights
Trieste to Pula cycling tour, self guided
Self-guided cycling tours through Italy, Slovenia and Croatia
From
€590 to €760
8 days
ex flights
Cycling holiday across Italy, Puglia to Sorrento
Ride across the boot of Italy
From
£2049 to £2099
8 days
inc UK flights
Puglia cycling tour
Reasonable easy cycling. Excellent bikes. Good weather.
From
£1749 to £1859
8 days
inc UK flights
Dolomites cycling holiday in Italy
The Dolomites, while avoiding the need to ride up any long climbs
From
£1549 to £1649
8 days
inc UK flights
Cycling holiday in the Prosecco Hills, Italy
A great variety of scenic roads and picturesque rolling hills
From
£1499 to £1599
8 days
inc UK flights
Umbria to Tuscany cycling & cooking holiday
Cycling and cooking holiday between Umbria and Tuscany
From
€1120 to €1160
6 days
ex flights
Tuscany cycling holiday through Siena & Chianti, Italy
Cycle the most evocative and romantic landscapes
From
£1529 to £1699
8 days
inc UK flights
Cilento and Amalfi Coast cycling holiday, Italy
Rocky ridges set between small picturesque inlets
From
£1699 to £1899
8 days
inc UK flights
Sicily cycling holiday in Italy
Ride through Sicily's UNESCO sites of Siracusa, Noto, Modica and Ragusa
From
£1399 to £1849
8 days
inc UK flights
Umbria cycling holiday
Scenic pedalling through olive groves and historic towns
From
£1695 to £1809
11 days
inc UK flights
E-bike tour from Italy to Austria
Bike through Italy, Croatia, Austria and Slovenia
From
€2090
8 days
ex flights
Highlights of Puglia cycling holiday
Explore Italy's beautiful, sun-drenched Puglia region
From
£1879 to £1999
11 days
inc UK flights
Tuscany self guided cycling holiday in Italy
Experience local Tuscan life on two wheels
From
£1679
8 days
inc UK flights
Venice cycling holiday, Italy
Venetian countryside surrounded by olives, poplars and cherries
From
£1245 to £1299
8 days
inc UK flights
Single track mountain biking holiday in Europe
Biking "off the radar" trails in Slovenia
From
€1760
8 days
ex flights
Matera to Lecce cycling holiday in Italy
Discover the jewels of Southern Italy from Matera to Lecce
From
€710 to €1710
8 days
ex flights
Chianti self guided cycling holiday in Italy
Pedal through the archetypal Tuscan countryside
From
£1835 to £1969
11 days
inc UK flights
Cycling holiday in Italy and Switzerland
Cycling with the spectacular scenery of the Italian Lakes
From
£1879 to £1979
8 days
inc UK flights
Cilento to the Amalfi Coast cycling holiday
Cycle the dramatic coastline of Cilento National Park
From
£1435 to £1572
8 days
inc UK flights
Pisa to Florence cycling holiday, Italy
The highlights of beautiful Tuscany by bike
From
£760 to £900
8 days
ex flights
Piedmont self guided cycling holiday in Italy
Rolling hills, sun-drenched hamlets and exquisite wines
From
£1465 to £1809
9 days
inc UK flights
Alpine Cols of the Tour de France
Spectacular cycling route through the Italian and French Alps
From
£1479 to £1579
8 days
inc UK flights
E-Bike cycling holiday in Umbria and Tuscany
Pedal your way through the rolling Tuscan hills by e-Bike
From
£1095 to £1895
8 days
ex flights
Piedmont cycling holiday, Italy
Softly rolling hills & sun-drenched hamlets
From
£2185 to £2399
9 days
inc UK flights
Florence to Pisa cycling holiday
Fall in love with provincial Italy on this cycling adventure
From
£1440
8 days
ex flights
Self guided Puglia cycling holiday
Cycle the heel of Italy in the sun drenched region of Puglia
From
£0
1 days
inc UK flights
Pisa to Florence cycling holiday in Tuscany
Cycle between two iconic cities and pedal through delightful Tuscan landscapes
From
£1599 to £1779
8 days
inc UK flights
Italy cycling holiday, Venice & Veneto
Wonderfully easy cycling route exploring the pretty villages
From
£1415 to £1469
9 days
inc UK flights
TAILOR MADE OR SMALL GROUP CYCLING?
Italy cycling holidays fall into two camps: small group trips with a guide, or tailor made holidays that are self guided. If you enjoy the social side of cycling, and the reassurance of cycling with a tour leader who knows the language, the points of interest and the best places to eat, then small group cycling in Italy may be your thing. On the other hand, if you prefer to cycle at your own pace, enjoy reading route notes and following a map, but also quite like the thought of your luggage ready and waiting for you at the next hand-picked small hotel, then tailor made cycling tours in Italy are going to put the most air in your tyres.
David Sear and Andrew Ross, experts from one of our leading European cycling holiday companies, Exodus, share their advice on tailor made and small group cycling holidays in Italy:
Andrew Ross: “I love the atmosphere and camaraderie of a cycling group, but every once in a while you cannot beat heading off on your own and losing yourself in the experience of riding in a foreign land. After years of exploring on two wheels it is very apparent that there are always many different ways of getting from A to B and the actual planning of a daily route is also something that I find very rewarding. For these reasons I do love the self guided concept.”
David Sear: “Group cycling holidays allow you to travel solo and meet likeminded people who all enjoy cycling and have a sense of adventure. I think it really adds to the experience when you share the trip with other people; on our challenging trips the physical effort really brings the group together, whereas on our leisurely trips the group provides a great atmosphere, conversation and fun. You are guaranteed to make friends on a group tour and having a local guide to give you all the information means you don’t miss a thing.”
Andrew Ross: “The great thing about a guided ride is that the tour leader will share their knowledge and passion for what is likely to be their home region. Not only will you learn a huge amount about the history and culture, but you’ll also get a genuine insight into life here. Whether you’re in a group or on a self guided trip, Italy is the perfect destination as cycling is ingrained within the culture.”
Our top Italy cycling Holiday
Matera to Puglia cycle in Italy
Nestled between the Adriatic and Ionian seas
From
£1499 to £1899
8 days
inc UK flights
Small group travel:
2021: 4 Apr, 25 Apr, 2 May, 9 May, 12 May, 16 May, 23 May, 6 Jun, 13 Jun, 20 Jun, 4 Jul, 29 Aug, 5 Sep, 8 Sep, 12 Sep, 15 Sep, 19 Sep, 26 Sep, 3 Oct, 10 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
2021: 4 Apr, 25 Apr, 2 May, 9 May, 12 May, 16 May, 23 May, 6 Jun, 13 Jun, 20 Jun, 4 Jul, 29 Aug, 5 Sep, 8 Sep, 12 Sep, 15 Sep, 19 Sep, 26 Sep, 3 Oct, 10 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
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.
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More about Italy cycling
The best time to go on a cycling holiday in Italy is May or September although the further south you cycle the longer the season extends.
If you’ve always fancied a cycling holiday in Italy but didn’t know where to start, don’t panic; we’ve got cycling in Italy covered from top to toe.
Cycling holidays in Italy come in all shapes and sizes, from relaxing foodie tours to challenging mountain rides.
Although Italy’s Amalfi Coast has long been a haven for glitz and glamour, it’s also provided cyclists with some of the world’s most scenic coastal rides.
Cycling in Puglia has a lot to recommend it: the heel of Italy’s boot is flat, as well as dry and sunny.
Cycling in Sardinia lets you explore the island’s magnificent natural beauty while avoiding overcrowded beaches and resorts.
Read our top 10 cycling holidays in Italy and find out where you could be pedalling off to in the not too distant future.
Find out what our Italian cycling experts have to say about where to ride, what to pack and why preparation is the key to successful cycling holidays, in our Italy cycling advice.
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