Italy Cycling Tours

Italia! Pizza! Pasta! The Giro! Italy is a classic cycling destination with a huge variety of landscapes to explore & a history steeped in cycling culture. Italy is best enjoyed from April through to June and in the Autumn months.

OUR FAVOURITE cycling tours in Italy

Custom Custom Custom Custom


from €1.499

Custom hotels
Self guided
Custom kms
Custom m
Strade Bianche
Italy5 daysAdvancedRoad

Strade Bianche

€ 3.299

Welcome to Tuscany & the drama of Strade Bianche! Race the Strade Bianche Gran Fondo & spectate the pro race as it blasts through the Tuscan countryside. Cycle through the vineyards of the Chianti region and discover hilltop villages galore.

309 km
4120 m
TuscanyTop seller
Italy7 daysIntermediateRoad

Tour of Tuscany

€ 4.499

Welcome to Tuscany! Ride through the stunning Tuscan countryside, cycle through the vineyards of the Chianti region and discover hilltop villages galore.

320 km
5850 m
Trans Dolomites ChallengeTop seller
Italy8 daysEpicRoad

Trans Dolomites Challenge

€ 4.799

Cycle from Monte Zoncolan in the Carnic Alps, through the spectacular Dolomites & on to the Italian Alps taking in iconic climbs of the Giro d’Italia along the way. Discover the beauty of the Sella Ronda, climb with the ghost of Pantani on the Mortirolo, channel your inner Dumoulin on the slopes of the Stelvio.

507 km
15271 m
Classic Climbs of the Giro
Italy7 daysAdvancedRoad

Classic Climbs of the Giro

€ 3.399

Tackle the classic cycling climbs of the Giro d’Italia in Northern Italy. Ride out of two locations: Corvara in the Dolomites & Bormio in the Italian Alps and climb the most impressive climbs the region has to offer.

440 km
11045 m
Prosecco HillsNew
Italy7 daysIntermediateRoad

The Prosecco Hills

€ 4.999

Join us on a jaunt around the UNESCO Prosecco hills and visit iconic climbs of the Giro d'Italia.

362 km
5260 m
Show all tours


Italy team




Cyclist’s Guide To Italy

Italy has a special place in Eat Sleep Cycle history and we cannot wait to return to bring more of our amazing guests to this incredible country in the not too distant future. Italy has cycling deeply embedded in its culture & history. Capturing the depth of riding, the variety of terrain, the passionate cycling […]

Bikes & Gear

Why You Should Book a Custom Cycling Vacation

Any cycling tour is guaranteed to be an amazing and unforgettable experience of a lifetime, but if you want to take your cycling tour to the next level, or travel as a family or large group then perhaps it’s time to consider a custom cycle tour. Maybe you are thinking of travelling with friends and […]

Top 5 European Cycling Tours- The Most Popular 2019 Cycling Tours - Eat Sleep Cycle
Bikes & Gear

Top 5 European Cycling Tours: The Most Popular 2019 Cycling Tours

The cycling season is now well underway and we’ve already seen hundreds of guests fulfil their cycling dreams and experience some of the best cycling locations that Europe has to offer. Some destinations, however, are more popular than others, and when you look closer it’s obvious as to why: they’re simply amazing places to ride […]

1 2 3



What happens if I need to cancel the trip?

We have a flexible cancelation policy – please take a look at our cancellation policy at the time of booking. If you have any doubts please reach out and we’re happy to help.


Is the tour the right level for me?

We rate our tours from Level 1 (Leisure) to Level 4 (Epic). Each tour contains a description of the level, expected daily ride time, distance and elevation. If you have any doubts we’re more that happy to speak to you on the phone and help to find you the perfect trip!


What about bikes? Can I hire one or should I bring my own?

We recommend that you hire a bike for your tour and will work with you after you book to help you to choose the best size and model for your ride style. If you prefer to bring your bike, it’s no problem. Please be aware that on some of our epic trips we charge a supplement to transport your bike box to our finishing location. If you have any doubts, please ask!


Is insurance included?

Insurance is not included in our tour packages. We highly recommend contracting travel insurance at the time of reservation with a company from where you are from.

Health insurance which covers you for illness or injury whilst cycling in your chosen destination is mandatory, we’ll ask you for details of your insurance providor before you travel.