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.
Here are a few of our cycling holiday locations in Italy, which offer you the possibility of multiple destinations in one trip.
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.
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.
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.
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.
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.
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Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello and whitewashed Ostuni.
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From the northeastern Dolomites, cycle through the Alta Val Pusteria below the famous Drei Zinnen, through the valley of the ice cream makers and across the plains to reach Venice.
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This trip combines scenic pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include panoramic Montefalco, picture-postcard Spello and ancient Assisi.
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This 11 night cycling holiday starts in UNESCO Matera, in the Basilicata region and moves on to Puglia. Discover unspoilt villages and gently rolling hills, sandy beaches and interesting towns. Highlights include whitewashed Ostuni and Baroque Lecce.
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Taking you from the stunning Dolomites to Venice. The cycle route starts at the Brenner Pass, on the border with Austria and you'll follow gentle riverside tracks through fragrant orchards and vineyards. Enjoy a ferry ride across Lake Garda and continue through the beautiful cities of Verona, Padova to the canals and waterways of Venice.
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The perfect choice for people wanting a genuine grass-roots Italian experience. You'll stay on a family-run farm, in the heart of the Venetian countryside, with private pool and vineyards. Venice, Verona and Padua are all possible day trips.
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Spectacular riding from the stunning Dolomites to Venice. Starting from Bolzano, the capital of the South Tyrol, you'll follow gentle riverside tracks through fragrant orchards and vineyards to reach Lake Garda. Ride through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.
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Wonderfully easy hotel-to-hotel cycling route exploring the pretty villages, villas and castles of the Venetian countryside. Lots of historic interest and great regional cooking! A day trip to Venice is a 'must' with Padua and Vicenza also within reach.
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Explore the undiscovered western coast of Sicily by bike to find pristine nature reserves, ancient monuments and Baroque towns. Highlights include Segesta's amphitheatre and Selinunte Archeaological Park.
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Introducing you to quintessential Tuscany, this cycling holiday has all the ingredients to create a wonderful lasting impression of this rightly famous region. The landscapes, the food, the people and, of course, perfect cycling routes. This is not just a cycling holiday it is an immersion into local Tuscan life.
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This eight-night, self-guided cycling holiday provides a wonderful introduction to Sicily's south east, a part of the island renowned for its beautiful, unspoilt coastline, spectacular Baroque architecture and sumptuous regional cuisine.
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Our 10 night holiday takes you from the turquoise waters of Lake Bled, nestled below Slovenia's jagged Julian Alps, along the Alpe Adria Trail, passing into Italy. Wind down through the mountains to the island of Grado on the Adriatic coast. On route pass through the historic towns of Venzone, Udine and Palmanova.
DEPARTURE MONTHS
Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello and whitewashed Ostuni.
DEPARTURE MONTHS
Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night cycling holiday! The cycling takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.
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Embark on a picturesque cycling journey from Venice to Poreč, immersing yourself in the stunning landscape and rich cultural heritage. Explore historic towns such as Trieste and Piran, indulge in delicious cuisine and experience the beauty and diversity of the Adriatic coast on this unforgettable cycling adventure.
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Cycle from the iconic leaning tower of Pisa to the Ponte Vecchio in Florence, passing through beautiful Tuscan landscape that inspired artists and composers such as Leonardo da Vinci and Puccini. The gentle cycling is mainly along riverside paths and quiet roads.
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Journey between seven beautiful Italian Lakes as you explore this colourful and cultural region.
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Cycle through the heart of the San Gimignano region and its stunning surroundings. Ride through cypress dotted rolling hills, meander through valleys adorned with sunflower and poppy fields and explore Tuscany’s hilltop towns.
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Discover the flavours and art cities of Emilia Romagna on this tasty tour pedalling from Bologna to Parma.
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Superb cycling discovering the south west of Sardinia, with its glittering turquoise seas and pure white sand beaches. The trip includes island hopping to St Antioco and St Pietro, visiting the archaeological site of Nora and pedalling along Sardinia's spectacular Costa del Sud.
DEPARTURE MONTHS
Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello, whitewashed Ostuni and beautiful Baroque Lecce.
DEPARTURE MONTHS
Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night cycling holiday! The cycling takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.
DEPARTURE MONTHS
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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.
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.
We offer four different levels across our cycling trips 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.
The bikes you'll be riding during your trip will have the following features:
We also have e-bikes and tandem bikes available on selected holidays.
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.
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.
