Italy Cycling Tours | Cycling Holidays in Italy | Eat Sleep Cycle
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Italy

Italy
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Cycling Holidays in Italy

Italia! Pizza! Pasta! The Giro! Italy is a classic destination for cycling holidays, 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.

Italy cycling tours offer something special for every cyclist. Whether you’re looking for mountain ranges, excellent food or to ride around the lakes, our cycling holidays in Italy have you covered.

From the high mountains of the Alps and Dolomites in the North, to the Italian Lakes of Lombardia & Piemonte, to the rolling hills of Tuscany and Emilia Romagna, and off-shore to the islands of Siciliy & Sardinia, Italy promises to wow!

OUR FAVOURITE cycling tours in Italy

Florence to Rome Gravel - Self Guided
Italy
|
7 days
|
Advanced
|
Gravel

Florence to Rome Gravel - Self Guided

1999.00
Ride the ancient pilgrimage route of the Via Francigena from Florence…
4
Self Guided
449 km
7,725 m
New
Dolomites & Italian Alps Everesting Challenge
Everesting
|
6 days
|
Epic
|
Road

Dolomites & Italian Alps Everesting Challenge

3499
Keen on an unforgettable Dolomites climbing experience? Join an official Everesting…
Next Departures
29 June 2026
3
4
Scheduled
439 km
13,655 m
New
Strade Bianche
Italy
|
5 days
|
Advanced
|
Road

Strade Bianche

3299.00
Welcome to the picturesque Chianti region for a warm welcome to…
4
Custom tours
309 km
4,120 m
Tour of Tuscany Self-Guided
Italy
|
6 days
|
Intermediate
|
Road

Tour of Tuscany Self-Guided

2199.00
Soak up the Tuscan sunshine at your own pace on our…
4
Self Guided
215 km
4,550 m
Tour of Piemonte
Italy
|
7 days
|
Intermediate
|
Road

Tour of Piemonte

3899.00
Discover a hidden gem & unknown cycling paradise in the north…
3.5
Custom tours
382 km
5,200 m
Classic Climbs of the Giro
Italy
|
7 days
|
Advanced
|
Road

Classic Climbs of the Giro

3399.00
This is an epic tour designed for big mountain-lovers. Tackle up…
4
Custom tours
440 km
11,045 m
The Prosecco Hills
Italy
|
7 days
|
Intermediate
|
Road

The Prosecco Hills

4999.00
Join us on a jaunt around the UNESCO Prosecco Hills on…
4
Custom tours
362 km
5,260 m
New
Florence to Rome Gravel
Italy
|
7 days
|
Intermediate
|
Gravel

Florence to Rome Gravel

3799.00
Ride the ancient pilgramage route of the Via Francigena from Florence…
Next Departures
29 September 2025
25 May 2026
28 September 2026
4
Scheduled
449 km
7,725 m
New
Trans Dolomites Challenge
Italy
|
8 days
|
Epic
|
Road

Trans Dolomites Challenge

4499.00
Welcome to the beautiful Dolomites. The tour begins in the charming…
Next Departures
8 September 2025
6 July 2026
7 September 2026
4
Scheduled
507 km
15,271 m
Top seller
Tour of Tuscany
Italy
|
7 days
|
Intermediate
|
Road

Tour of Tuscany

3699.00
Welcome to the picturesque Chianti region, a perfect place to be…
Next Departures
13 October 2025
27 October 2025
1 June 2026
4
Scheduled
320 km
5,850 m
Top seller
Tour of Sicily
Italy
|
6 days
|
Intermediate
|
Road

Tour of Sicily

3899.00
Join us on on the beautiful island of Sicily and discover…
4
Custom tours
282 km
5,560 m
Custom Tours
Custom
|
Custom
|
Custom
|
Custom

100% CUSTOM TOUR

1723
Custom hotels
Self Guided
Custom kms
Custom m
Custom

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.

Italy Team

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.

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.

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!

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!

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.

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.

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FAQs

1
What happens if I need to cancel the trip?
We have a flexible cancelation policy - please take a look at our cancellation policyat the time of booking. If you have any doubts please reach out and we're happy to help.
2
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!
3
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!
4
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 provider before you travel.

Any Questions?
Contact Us