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Cycling Holidays in Italy

Our cycling holidays in Italy offer a unique way to explore the country’s varied landscapes and rich heritage. From steep climbs of the Dolomites and Alps to cruising through Tuscany and the coastlines of Sardinia, there’s something for every rider at every level. 

Whether you’re drawn to quiet country roads, challenging mountain passes, or lakeside routes, Italy combines great cycling with incredible food, local wine and a deep cycling culture. An Italian cycling holiday is the perfect blend of adventure and discovery, best enjoyed in spring or autumn. Discover our tours today.

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Our Favourite cycling tours in Italy

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Italy Highlights

Romeo & Juliet

Romeo & Juliet

Shakespeare’s balcony is in the city of Verona and is a symbol of romance & tragedy, and the perfect place to finish a beautiful cycling adventure!

The Italian Lakes

The Italian Lakes

The lakes region in northern Italy are the playground of the rich and famous and for cyclists too! Lake Garda & Lake Como are just two of a stunning network which must be visited on our Italian cycling tours.

Strade Bianche

Strade Bianche

The white gravel roads of Tuscany play host to the world-tour race every March. The race starts and finishes in the Tuscan city of Siena.

Passo Gavia

Passo Gavia

The Passo Gavia has it all: stunning scenery, narrow tarmac, a pitch black tunnel and an illustrious cycling history. In 1988 Andy Hampsten battled apolcalyptic conditions crossing the snowy pass to take the Giro lead and cement the Gavia’s place in cycling legend.

Passo Stelvio

Passo Stelvio

The Stelvio needs little introduction. At an elevation of 2,757 m the Stelvio is the second highest pass in the Alps and links Bormio in the south to Prato & Switzerland. A regular feature of the Giro D’Italia, the Stelvio is notorious for its 48 hairpins and is certainly a highlight of our Italy cycling tours.

The Sella Ronda

The Sella Ronda

This Italian cycling route is a must for anyone riding in the Dolomites. The Sella Ronda offers a 50 km loop with mind-blowing views across the four climbs of the Campolongo, Gardena, Pordoi and Sella.

ICONIC CLIMBS

Tackle legendary Giro d’Italia passes in the Alps, Dolomites, and Apennines, routes that define European road cycling.

RICH CYCLING CULTURE

Ride in a country where cycling is a deep-seated passion - embraced by riders, cheered by locals, and honoured in every region.

DIVERSE LANDSCAPES

From high mountains to rolling vineyards and coastal roads, Italy offers every kind of terrain, all on beautifully rideable routes.

FUELLED BY FLAVOUR

Every ride ends with something delicious. Enjoy fresh pasta, authentic pizza, regional wines and the perfect post-ride espresso.

Italy Team

Lydia

Lydia

Lydia is an ex-pro track cyclist and engineer from Ireland. She’s lived in Spain for many years and recently relocated to Girona to focus on her career as a guide.

Eloi

Eloi

After leaving his career as an Engineer to explore the world by bike with his partner, Eloi has returned home to Catalunya to
start a new career as a guide. Eloi has a deep love of life on two wheels and the great outdoors – he’s looking forward to the adventure with you!

Matteo

Matteo

Matteo is from the shores of Lake Como but has spent a lifetime travelling and guiding all over the world. Matteo brings good humour and a wealth of hospitality & guiding experience to the team.

Gethyn

Gethyn

Gethyn is from Wales but has been living in Catalonia for 14 years, and having found a quiet spot in the forest not far from Girona, he has no intention of leaving. Gethyn’s been a part of the ESC team since the early days and loves the job. He rides road and gravel with friends and MTB with his dog.

Emanuela

Emanuela

Emanuela is Italian and after many years living in Barcelona relocated to Mallorca. She started triathlon 10 years ago and has made it her life! Alongside guiding Emanuela hosts guests from all over the world in her Airbnb.

Mario

Mario

During the past 10 years, Mario has lived in different countries, but now he’s back home in Conegliano to ride every steep hill in the area! Despite his focus on road cycling, he’s had some amazing moments with his beloved steel gravel bike! Mario has been a member of the ESC Team since 2019 and couldn’t be happier! He looks forward to seeing you on the road soon!

Find Out More About

Italy
Why is cycling popular in Italy? 
Italy

Why is cycling popular in Italy? 

It’s difficult to meet with cyclists for a ride, or just a coffee, and not touch on the subject of cycling in Italy in some...

The best cycling routes in Italy
Italy

The best cycling routes in Italy

We have spent years curating the best cycling routes in Italy to give you the chance to ride these roads. But our passion for cycling...

Italy Cycling Rules 101
Italy

Italy Cycling Rules 101

Even if you’ve been cycling in Italy before, we recommend reading these tips and best practices as a brief reminder before your trip. 

FAQs

1
What level of fitness or cycling experience do I need?
You don’t need to be a pro, but you should have regular cycling experience and some comfort with sustained riding and climbs. 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 than happy to speak to you on the phone and help to find you the perfect trip!
2
When is the best time of year to cycle in Italy?
The prime seasons are spring (April to June) and autumn. During these periods you’ll usually get milder weather, fewer crowds, and more stable road conditions. Summer can be hot and busy, especially in popular regions.
3
Which regions or routes are ideal for a cycling holiday in Italy?
Italy’s variety is one of its strengths. Popular options include: - The Alps and Dolomites for epic climbs and alpine scenery - Tuscany and Chianti for rolling vineyard landscapes and Strade Bianche roads - Piemonte and the Langhe wine country for quieter hills - Sicily for coastal riding, inland climbs, and Mount Etna - The Prosecco Hills for beautiful roads and Giro d’Italia heritage You can pick tours by region or style (road, gravel) depending on your preference.
4
Are there self-guided or custom cycling tours available?
Yes, there are self-guided options where you ride independently with route support, as well as custom and private tours tailored to your needs. This flexibility means you can ride at your own pace, or opt for guided support if preferred.
5
Do I need to bring my own bike, or can I hire one locally?
You have both options. A fleet of high-quality rental bikes (road, gravel, e-bikes) is available, but if you prefer to bring your own, that’s possible too. It’s best to check at the time of booking to confirm arrangements.
6
What safety rules or cycling etiquette should I be aware of in Italy?
A few key points: - Always ride on the right side of the road - In urban areas, riding two abreast is tolerated; outside towns you may be expected to ride single file - Lights are recommended, and reflective gear is required outside urban areas from sunset until half an hour before sunrise These guidelines help ensure safety and respect for local traffic norms.
7
What happens if I need to cancel or change my booking?
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.
8
Is Italy suitable for first-time or family cycling holidays?
Absolutely, though you’ll want to choose a moderate route. Some tours feature gentler hills, scenic backroads, and shorter daily distances, which are well suited for beginners or families. Italy’s rich cultural and culinary attractions also make it a rewarding destination for non-riders.

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