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Cycling Holidays in Italy

Join us for a cycling holiday in Italy for your chance to explore stunning countryside, dramatic coastline and of course world-famous culture. The Skedaddle Italia team are a passionate bunch and excited to share their love and knowledge for this country. With fantastic on-hand support and expert local advice, our holidays here offer the very best experience possible.  

We've lots of great cycling options here that are available as both self-guided and fully guided tours. Popular locations include exploring idyllic landscapes in Tuscany, the dramatic Cilento and Amalfi Coast, as well as holidays with food in mind in Piemonte and Sardinia.

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Found 5 holidays

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This cycling holiday in Austria and Italy, is ideal for those wishing to experience the beauty of the Alps in style. At times somewhat challenging, the riding is concentrated along the Via Claudia Augusta, a 2000 year old Roman built road which was for many centuries the main commercial route across the Alps. Originally used f... .. Read More

Prices From:

£1,520 p.p.

8 days

Departure Dates
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Trips to book before it's too late. For all other dates check-out the Departure Dates menu below

25 Mar to 1 Apr - A beautiful backdrop of outstanding colours, perfumes and crystal clear emerald seas will accompany you throughout the week. Sounds good? Book now...

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Cycling in Sardinia really doesn't get much better than this! Our Island Flavours holiday will see us cycling in Sardinia's south-west corner, a region bursting with variety; from expanses of vineyards, olive groves and oak wooded valleys, to high rugged cliffs dotted with Spanish watchtowers and splendid beaches, hiding seclude... .. Read More

Prices From:

£1,310 p.p.

8 days

Departure Dates
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Trips to book before it's too late. For all other dates check-out the Departure Dates menu below

28 Apr to 4 May - On this journey you will explore some of the best towns of the regions, including: Volterra, San Gimignano, Monteriggioni and Siena.

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This fantastic cycling holiday in Italy really showcases the beautiful Tuscan countryside. Rural Tuscany is synonymous with undulating green hills capped by medieval tile-roofed towns punctuated by cypresses, churches and stone farmhouses. The rolling green countryside will be the backdrop for most of our ride and we'll have the... .. Read More

Prices From:

£1,295 p.p.

7 days

Departure Dates
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Trips to book before it's too late. For all other dates check-out the Departure Dates menu below

14 to 21 Apr - Escape the crowds of central Italy and head to the heel for your chance to discover one of Italy's lesser known, but none-the-less beautiful landscapes.

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0 1 2 3 4 5

A guided cycling holiday exploring the Apulian region of Italy, located in the southeast in what is commonly known as the heel of Italy's boot – (and it's also its best kept secret!) This interesting and eclectic region is steeped in history and has been governed by the Greeks, Romans and Spaniards over the centuries,... .. Read More

Prices From:

£1,455 p.p.

8 days

Departure Dates
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0 1 2 3 4 5

Join us on this guided cycling holiday in Italy where we'll be tracing the steps of the ViaFrancigena, an ancient route packed full of historical gems and idyllic Italian countryside. Once the favoured route for merchants, armies and pilgrims travelling from Canterbury to Rome (and all the way through to Jerusalem), our version ... .. Read More

Prices From:

£1,610 p.p.

9 days

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Skedaddle News, Views and Holiday Stories

Customer Story: Bike, Boats and Pizza

We’ve been receiving some fantastic holiday photos and memories from you all Summer and its great to see how you’ve been getting along on your cycling holidays! One family returning from a leisure cycling holiday from Lake Garda to Venice in Italy sent us in a great selection of smiling cycling shots as well as ... 

Last Updated: 01/09/2017

Tuscan Tastes: Buon appetito!

dire pane al pane e vino al vine Translation: Call bread bread and wine wine… This classic Italian phrase means you should simply ‘tell it how it is’, an important philosophy which soaks into the country’s authentic approach to cooking… History, location and lashings of sunshine combine to create foodie heaven in Italy, a land ... 

Last Updated: 01/04/2016

Movers and shakers…

Thinking ahead to the New Year and in need of a little inspiration for your next cycling holiday? We’re taking a look at some of our most popular destinations, which are already proving a hit in 2016… The striking white towns of Puglia beckon cyclists with their promise of fewer tourists and stunning beauty, far from the busy ... 

Last Updated: 15/12/2015

Popular leisure tours in 2015

From azure coastlines to lush, alpine backdrops, our leisure bestsellers offer a unique insight into some of the world’s most spectacular destinations… For an epic cross-country adventure we recommend the Via Claudia, which takes you from the dramatic foothills of the Alps in Austria, to the sparkling shores of lovely lake Garda in Italy. Following ancient ... 

Last Updated: 16/11/2015



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