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Road Cycling Holidays in Italy

Here at Saddle Skedaddle, we offer a fantastic choice of road cycling holidays in Italy for you to choose from.

We offer the option of guided road cycling holidays in Italy as well as self-guided road cycling holidays in Italy, meaning there’s something to suit all abilities and preferences. Discover the stunning Italian countryside and coastline as you cycle through some of the most beautifully unspoilt regions of Italy, experiencing the fresh air and peaceful surroundings all at your own pace.

Our road cycling holidays in Italy are graded to make sure they are suitable for all riders. Italy offers a great range of scenery and landscape, from the dramatic to the serene, making it an extremely popular road cycling holiday destination.

If you’re not 100% set on a road cycling holiday in Italy, then don’t forget to have a look at our range of road cycling holidays in Spain, as well as our choice of road cycling holidays in France and throughout Europe.

Use the tabs below to find out more information about our road cycling holidays in Italy, request trip notes and book online today.

Not looking for Road Cycling Holidays in Italy?

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Found 9 holidays

Here's our featured trips. For all departure dates see menu below.

09 to 20 May - Don't miss our latest Grand Tour date! A fantastic exploration of some of Europe's finest coastal routes. Guaranteed to run.

France and Italy - Grand Tour of the Med - Road Cycling Holiday Thumbnail
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This superb road cycling holiday in France and Italy has become our signature road cycling tour and deservedly so with its miles of great classic riding; it really is a distinctly varied cycling adventure. Following arrival and an evening of superb Nicoise cuisine in the chic capital of the French Riviera, we ride out of tow...
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Prices From:

£1,985 p.p.

Duration: 12 days

Departure Dates
TRIP NOTES

Here's our featured trips. For all departure dates see menu below.

12 to 19 Apr - Explore this exotic Italian island by road bike and discover the many historical sights as you cycle along - just one space left!

07 to 14 June - Looking for sparkling sea's and white sandy beaches? Look no further! Guaranteed to run and getting full!

Italy - Sardinia - Coastal Explorer - Guided Road Cycling Holiday Thumbnail
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A coastal road cycling holiday in Italy on the island of Sardinia. Famed as Italy's most exotic island, it is blessed with a fantastic network of well-surfaced and car-free roads and you'll be assured of some great cycling. The island has a stunning coastline which we will explore throughout this cycling tour. Starting in th...
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Prices From:

£1,080 p.p.

Duration: 8 days

Departure Dates
TRIP NOTES

Here's our featured trips. For all departure dates see menu below.

20 to 27 June - Take on the mighty Dolomites and awesome Alps during this challenging road cycling tour. Time to get your climbing legs on!!

Italy - Dolomites & Alps - Road Cycling Holiday Thumbnail
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This is a great example of a challenging road cycling holiday in Italy that visits the Italian Alps and the mighty Dolomites. Huge castles, vineyards and dramatic mountain peaks mark the far north of Italy as a genuinely special riding destination. To the north are the High Alps of Austria, to the west the Swiss Alps and to the ...
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Prices From:

£1,310 p.p.

Duration: 8 days

Departure Dates
TRIP NOTES

Here's our featured trips. For all departure dates see menu below.

27 June - 04 July - Explore the lovely Italian Lakes during a week of beautiful road cycling and gorgeous food and wine - guaranteed to run!

Italy - Lakes of Lombardia - Road Cycling Holiday Thumbnail
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A superb road cycling holiday in Italy which explores the Nothern Lake District, an area synonymous with cycling history. The Giro d'Italia almost always visits the region and, perhaps even more famously, it is the setting for the Tour of Lombardy, or "the race of the falling leaves", the Autumnal one-day classic which, each yea...
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Prices From:

£1,270 p.p.

Duration: 8 days

Departure Dates
TRIP NOTES

Here's our featured trips. For all departure dates see menu below.

20 to 27 Sept. - Timeless Tuscany on this road cycling tour in Italy. Beautiful accommodation and gorgeous food complete an impressive holiday package.

Italy - Tuscany Tourer - Road Cycling Holiday Thumbnail
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An easy paced road cycling holiday in Italy that explores one of the country's premier cycling locations. Tuscany - the word itself is evocative, conjuring images of classic Italian landscapes, rolling hills, cypress trees and medieval hill-top towns. The region also offers superb cycling and is an international training gro...
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Prices From:

£1,270 p.p.

Duration: 8 days

Departure Dates
TRIP NOTES

Here's our featured trips. For all departure dates see menu below.

18 to 26 April - Discover the mountain routes of charming Sardinia - a Mediterranean gem perfect for road cycling

Italy - Sardinian Mountains - Road Cycling Holiday Thumbnail
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Our road cycling holidays in Italy have never been more popular and Sardinian Mountains is proving to be a great road cycling alternative to our ever popular Sardinia Coastal Explorer holiday. The island of Sardinia is a beautiful Mediterranean gem famous worldwide for its sea and its coasts, yet more than 80% of its territory i...
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Prices From:

£1,210 p.p.

Duration: 9 days

Departure Dates
TRIP NOTES

Here's our featured trips. For all departure dates see menu below.

18 to 25 July - Want to combine your love for challenging climbs and fine wine? Look no further! Our first trip of the year is now a confirmed departure. Join us in this special place in Italy.

Italy - Passes of Piemonte - Road Cycling Holiday Thumbnail
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Piemonte is the destination for this road cycling holiday in Italy. Situated in the far north western corner or Italy, surrounded by the Alps and sharing borders with France and Switzerland it is something of a hidden gem for cyclists. Almost half of Piemonte can be described as mountainous whilst most of the remainder is co...
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Prices From:

£1,190 p.p.

Duration: 8 days

Departure Dates
TRIP NOTES
Italy - Garfagnana - The Mountains of Tuscany - Road Cycling Holiday Thumbnail
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A fantastic road cycling tour in the undiscovered mountains of the Garfagnana region of Northern Tuscany in Italy. The chances are that you won't have heard of this region of Italy, but this is good for us, as it allows us to get off the beaten track of "tourist" Tuscany, yet we're close enough to still reap the advantages. ...
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Prices From:

£1,295 p.p.

Duration: 8 days

Departure Dates
TRIP NOTES

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Skedaddle News, Views and Holiday Stories

Brand New Grand Tour Date Added!

Roll up, roll up! Due to popular demand we’re pleased to announce that a brand new departure has been added to our Grand Tour Road Cycling Holiday. Exploring some of the most stunning coastal scenery in France and Italy, our … Continue reading

Last Updated: 19/02/2015

To Infinity and Beyond!

Intrigued by our brand new Hors Categorie tours? Coined by the French to name climbs that are beyond regular categorization, it’s no surprise these tours take on some of the big European climbs avid roadies dream of getting under their wheels! Specifically tailored to suit experienced … Continue reading

Last Updated: 11/02/2015

Mountain Riding: Thine be the Glory!

You may have heard us wax lyrical about our brand new Hors Categories tours and as well as a super tailored roadie schedule, each HC holiday also incorporates a RAID challenge to really kick things up a gear. Not heard of a … Continue reading

Last Updated: 03/02/2015

Road Cycling in Mediterranean Europe…

The lure of cycling in golden sunshine, under blue skies, set against a sparkling coastline is almost impossible to resist. Combine those things with stunning mountain scenery, fantastic fresh food and roads with un-rivalled views, it’s little wonder our Mediterranean road cycling tours remain amongst … Continue reading

Last Updated: 02/12/2014

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