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.


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

Matera to Puglia cycle in Italy

Nestled between the Adriatic and Ionian seas

From £1749 to £2279 8 days inc UK flights
Small group travel:
2022: 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
2023: 2 Apr, 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 8 Oct, 15 Oct
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.

Is an Italy cycling holiday for you?

Go on a cycling holiday in Italy if...

… you're a fabulous foodie. Every region boasts its own best dish, so try something new or stick to carb-filled spaghetti – there’s a reason why Italian cyclists love Lycra. … you're prepared for anything. Even if undertaking a guided cycling tour, it’s still pertinent to know what to do with a puncture and how to protect yourself from the elements if a flash storm strikes. … you're into safe cycling. Learn some of the Italian Highway Code, bring your own helmet, get yourself seen, unplug your ears, avoid grappa at lunchtimes, and stick to recommended routes. … you want to stretch your mind. Build a free day into a tour so you can explore ancient sites, read up on local history or just practise Italian at the local gelateria.

Don't go on a cycling holiday in Italy if...

… you only want to stick to cities. Cycling in and out of Italian traffic is not fun, it’s dangerous. We recommend rural roads and peaceful paths leading through vineyards to hilltop towns and villages; save city sightseeing for once you've stowed the wheels. … you're more hare than tortoise. You may be cycling, but you’re still on holiday, so be honest, slow down and know your limits before donning your wraparound shades, wiggling your bottom and pumping pedals like Mario Cipollini. … you tend to ignore advice. Self guided route notes and expert local guides provide all you need to have a safe and successful cycling holiday in Italy. Please don't ignore expert advice if you want your trip to be unforgettable for all the right reasons.
Written by Chris Owen
Photo credits: [Page banner: ickick] [Tailor made or small group: Lucio De Marcellis] [Andrew Ross Quote 1: TRAILSOURCE.COM] [David Sear Quote: Winniepix] [Andrew Ross Quote 2: Xavi] [Go/Don't go: TRAILSOURCE.COM]