Italy

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

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100% CUSTOM TOUR

from 1,697 $

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

Strade Bianche

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.

Next Departures:
4★
Scheduled
309 km
4120 m
essential tuscany
Italy6 daysIntermediateRoad

Tour of Tuscany Self-Guided

2,490 $

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

Next Departures:
4★
Self guided
215 km
4550 m
New
Italy7 daysIntermediateGravel

Florence to Rome Gravel

4,302 $

Ride a magical gravel route from Florence to Rome in the tyre tracks of L'Eroica and the Strade Bianche, discover the Via Francigena.

Next Departures:
9 June 2025 29 September 2025 25 May 2026 28 September 2026
4★
Scheduled
449 km
7725 m
New
Italy7 daysIntermediateGravel

Florence to Rome Gravel – Self Guided

2,264 $

Ride a magical gravel route from Florence to Rome in the tyre tracks of L'Eroica and the Strade Bianche, discover the Via Francigena.

Next Departures:
4★
Self guided
449 km
7725 m
TuscanyTop seller
Italy7 daysIntermediateRoad

Tour of Tuscany

4,189 $

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

Next Departures:
25 May 2025 16 June 2025 13 October 2025 27 October 2025 1 June 2026 5 October 2026
4★
Scheduled
320 km
5850 m
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Italy
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Italy

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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 policy at the time of booking. If you have any doubts please reach out and we’re happy to help.

1

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!

1

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!

1

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.

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