Cycling Holidays in Italy

Showing 23 out of 338 trips

There's something very special about Italy; Few countries on earth are as diverse as Italy, with mountainous terrain, sparkling coastlines, ancient history and sumptuous cuisine to enjoy.

Our cycling holidays in Italy are a great way to explore the famous sights and hidden gems that this beautiful country has to offer. From easy, flat- cycling through Venetian vineyards to exhilarating tours of Chianti, we have an array of different journeys for all abilities to enjoy .

Each of our guided and self-guided cycling tours in Italy gives you the opportunity to explore at your own pace, with the peace of mind that you won't get lost thanks to our handy GPS navigation system. Plus, accommodation is provided on all our cycling trips in Italy, so you don't need to worry about finding the best place to rest after a long day on your bike.



Many of our cycling tours in Italy have in-between days that allow you to explore by foot, using our detailed maps and route notes as your guide. These days are a great opportunity to delve into some of the tourist hotspots, getting up close to famous buildings and city centres.

Whether you're searching for a relaxing coastal route or a breathtaking journey through rolling countryside, our cycling tours offer something for everyone. Thanks to its relatively short flight time of roughly two hours, Italy remains one of the most popular holiday destinations for UK tourists. You can choose to add flights onto many of our cycling holidays to Italy, simply click on the dates and prices tab of your chosen trip to check availability.

Where can I go cycling in Italy?

Here are a few of our cycling holiday locations in Italy, which offer you the possibility of multiple destinations in one trip.

Veneto

Want to explore the luscious vineyards, olive groves, and sunflower fields that Italy is famous for? Veneto is one of Italy's most beautiful countryside locations. Admire panoramic views of the rolling countryside as you meander through hilltop villages and past apricot orchards, with day trips to Venice and Verona included.

Tuscany

Appreciate striking architecture as you cycle through the great artistic cities of Tuscany, spotting everything from the leaning tower of Pisa to the Duomo of Florence. Our cycling trips through Tuscany are a must for your bucket list.

Dolomites

The Dolomites are an iconic part of Italy's mountainous terrain, and we run multiple trips that pass through the area. You'll stop off at Venice and Lake Garda, and view stunning vistas of crystal-clear waters and endless vineyards.

Puglia

For those who love a sea view, our cycling holidays to Puglia cover sun-drenched coastlines and white sandy beaches. Here, you can uncover the UNESCO site of Alberobello and absorb the outstanding Baroque architecture of Lecce. 

Sardinia

With glittering turquoise seas and island-hopping opportunities aplenty, cycling holidays in Sardinia are special. Visit nearby St Antioco and San Pietro in one action-packed trip that will have you taking in everything from ancient archaeological sites to pristine beaches.

Italy : Puglia

Cycling the Heel of Italy - Alberobello to Lecce

£909


4.7 (40 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : The Dolomites

Cycling from the Dolomites to Venice

£1009


4.8 (6 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Umbria

The Wine Trails of Umbria Cycling

£1129


5.0 (1 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Cycling the Heel of Italy - Matera to Lecce

£1459


4.6 (10 reviews)

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Self-guided cycling

11 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Trentino

Brenner Pass to Venice Cycling

£1899


5.0 (2 reviews)

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Self-guided cycling

9 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Veneto

Heart of Veneto Cycling

£939


4.8 (72 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
single centre

Level: 1
Leisurely

Headwater
Navigation App

Italy : Veneto

Bolzano, Verona & Venice Ride

£1079


4.7 (18 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Printed route
directions

Italy : Veneto

Venetian Villas and Vineyards Cycling

£1079


4.7 (57 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 1
Leisurely

Headwater
Navigation App

Italy : Sicily

Secrets of Sicily Cycling

£1159


4.6 (22 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Tuscany

A Taste of Tuscany Cycling

£1219


4.9 (27 reviews)

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Self-guided cycling

7 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Sicily

Cycling through Baroque Sicily

£1479


4.4 (20 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Slovenia

Julian Alps to the Adriatic Cycling

£1889


4.8 (118 reviews)

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Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Puglia

Contrasts of Puglia Cycling

£1279


4.6 (123 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Piedmont

Gastronomic Barolo Cycling by e-bike

£2299


4.8 (88 reviews)

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Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Italian Lakes

Cycling Lake Garda with e-bike

£929


4.5 (2 reviews)

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Self-guided cycling

6 nights,
single centre

Level: 2+
Moderate plus

Headwater
Navigation App

Italy : Veneto

Adriatic Coast - Venice to Poreč Ride

£959

NEW FOR 2025

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Tuscany

Cycling in Tuscany: Pisa to Florence

£1089


4.6 (8 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Tuscany

Cycling the hills of San Gimignano by E-bike

£1359

NEW FOR 2025

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Self-guided cycling

7 nights,
single centre

Level: 2+ & 3

Headwater
Navigation App

Italy : Emilia Romagna

Emilia Romagna – Bologna to Parma Cycling

£1439


4.7 (3 reviews)

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Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Navigation App

Italy : Sardinia

Undiscovered Sardinia Cycling

£1459


4.7 (19 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Navigation App

Italy : Italian Lakes

Cycling the Italian Lakes

£1649


4.0 (1 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

Italy : Puglia

Highlights of Puglia Cycling

£1869


4.8 (11 reviews)

VIEW TRIP

Self-guided cycling

10 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

Headwater
Navigation App

Italy : Piedmont

Cycling the Wine Villages of Piedmont by e-bike

£2199


4.8 (5 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2+
Moderate plus

Headwater
Navigation App

    Cycling Holidays in Italy

    Overall customer rating, based on 653 reviews

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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.

Frequently asked questions

What can I expect from my cycling holiday in Italy?

Taking in beautiful surroundings is at the heart of our cycling trips in Italy. And we take care of all the details for you, , ensuring your luggage and belongings are  transported ahead for you, so you won't need to worry. To get the most out of your holiday, we recommend reviewing our four grades of routes before choosing your trip.

Another decision you'll need to make is whether to go for a guided or self-guided cycling trip during your time in Italy. Guided trips will include an experienced guide and a vehicle filled with everything from spare parts to puncture repair kits, plus fellow cyclists to journey with.

Meanwhile, a self-guided cycling trip in Italy will begin with a briefing to make sure you're all set with the appropriate equipment and any information you might need. Thanks to our Headwater Navigation App , which is available on most of our cycling holidays, you'll have tailored instructions for your route. This will provide live GPS mapping and interactive information at dedicated 'points of interest'. Conventional maps are also available.

Can I use an e-bike during my cycling holiday in Italy?

You can ride an e-bike on many of our cycling holidays. The main advantage is that you'll be able to tackle longer rides or any steep hills with ease, making trips more accessible for anyone with lower fitness levels. Find out more about our e-bike holidays.

What are the different levels of cycling holidays in Italy?

We offer four different levels across our cycling trips in Italy.

  1. Bike: Flat, gentle routes are what you can expect at this level, making them a good option for families or beginners .
  2. Bike: This is a good choice for anyone looking for more varied terrain but at a comfortable cycling level that doesn't require technical skill.
  3. Bike: You'll cover longer and more strenuous routes, meaning you must be a reasonably confident cycler.
  4. Bike: These are more challenging cycling trips through more demanding terrain across Italy.

What should I pack for a cycling holiday in Italy?

Having the right footwear is important to make sure you can ride comfortably during your cycling trip through Italy. On top of this, sun protection, such as SPF, sunglasses, and sun hats are advised, as well as water bottles to help you keep hydrated.

What type of bike will I ride during my cycling holiday in Italy?

The bikes you'll be riding during your trip will have the following features:

  • 21 gears
  • Straight handlebars
  • Mudguards
  • Pannier rack
  • Gel saddles
  • A set of panniers
  • Puncture repair kit & tyre levers
  • A pump
  • A lock
  • Phone holder
  • Headwater bike briefing

We also have e-bikes and tandem bikes available on selected holidays.

Can I add flights onto my cycling trip to Italy?

Thanks to its relatively short flight time of roughly two to three hours, Italy remains one of the most popular holiday destinations for UK tourists. You can choose to add flights onto many of our cycling holidays to Italy. Simply click on the dates and prices tab of your chosen trip to check availability.

Why choose a cycling holiday in Italy by Headwater?

Our trusted reputation means you can breeze through a booking with Headwater knowing that we have your best interests at heart. We're experts with over 35 years of experience to our name, and take the time to make sure your cycling holiday in Italy is one to remember. We have plenty of booking perks to take advantage of too.

We're reputable - Past customers have rated us highly on Feefo, due to the attention to detail we bring to every aspect of our cycling tours.

Spectacular  destinations - Our five-step process means we can tailor our holiday packages down to a tee, removing the need for you to take time compiling an itinerary.

We can take care of your flights - After providing us with a few details, we can arrange flights for your cycling holiday in Italy.

ABTA- and ATOL-protected - When you book with us, you'll be ABTA- and ATOL-protected so you can relax knowing that your booking will be risk-free. Find out more about what your key rights are when booking with us.

Award-winning cycling holidays - We're proud to run award-winning tours. With impeccable customer service and attention to detail, our company has been recognised by the British Travel Awards.

Sustainable Travel - Our People, Places & Planet plan reinforces our mission of running our tours as sustainably as possible while working towards becoming Nature Net Positive and reducing our impact on the surrounding environment.

ABTA- and ATOL-protected - You can book with confidence knowing our walking holidays in Italy are ABTA- and ATOL-protected. Find out more about what your key rights are when booking with us.

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