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Italy Short Break Cycling Holidays

Our Favourite Cycling Weekends in Italy

Italy has some gorgeous sights you can view on a cycling weekend, from the hills of Tuscany to the ancient city of Bologna.

As a holiday destination, Italy is famed for its stunning countryside, delicious cuisine, and passionate locals. The diverse landscape of verdant hills, dotted with picturesque wineries and historic castles, make a cycling weekend in Italy a must for your bucket list.

Exploring on two wheels is an ideal way to take in the glorious landscapes at a leisurely pace, working up an appetite to enjoy the delicious food and wine. And with easy flights to the cities of Perugia, Florence and Bologna, an Italy cycling weekend has never looked so appetising. 

Cycle through vineyards and olive groves, delve into the Renaissance art scene, and take in the spectacular countryside. For would-be cyclists wary of Italy’s famed hills, we offer e-bikes to give you an extra boost for exploring the hilltop towns of Tuscany and Umbria, so you can cover more ground on your Italy cycling weekend without getting too tired. 

For many travellers, the highlight of an Italian adventure is the food and wine. Italy’s diverse regions each offer their own local specialties. The wineries of Chianti in the Tuscan countryside surrounding Florence are amongst the most iconic in the world. Foodies should head to Emilia Romagna to learn how Parmesan cheese is made, or to explore Bologna – the foodie capital of a country renowned for its cuisine. 

Whether you’re seeking a few days of exploring at your own pace or prefer to get the inside scoop from an expert guide, we can tailor you an incredible cycling weekend in Italy.

The Umbrian Experience

Explore the famed Tuscan and Umbrian countryside on a guided cycling holiday. Starting on the Tuscany borders, this magical e-bike tour is a gourmet adventure into the hills and valleys of classic Umbria. After flying into Florence, pedal your way gently along quiet side roads and tracks, travel the ancient ‘via Flaminia’ highway of the Roman empire and feast on wondrous Italian fayre.

An e-bike tour is the perfect way to discover the rolling hills of the region. Gone are the days of huffing and puffing your way to the top; e-bikes make light work of the undulating terrain, leaving you free to take in the spectacular scenery with the wind in your hair. 

Up in the hills of southern Tuscany, with spectacular views of the surrounding valley and Lake Trasimeno, you’ll take in ancient castles of the Niccone Valley. Meander along riverside paths and country roads to medieval Montone where you’ll feast on a fabulous dinner prepared by celebrity chef, Giancarlo Polito. Cycle by Roman ruins and discover castles set amongst vineyards and olive groves. This timeless landscape inspired St Francis’ love of nature and his ideal that humanity and nature can coexist in harmony. If you’re looking to experience the best of Umbria on your Italy cycling weekend, this cycling tour is the perfect choice.   


Indulge yourself on Umbrian wines, delicious food and gorgeous scenes as you embark on a cycling holiday. Call our cycle experts today to find out more.

Umbria cycling holidays
Umbria Cycling Holidays

Flavours of Emilia Romagna

Treat yourself on our self-guided weekend cycling tour through Italy’s premier pasta region. Indulge in tantalising selections of balsamic vinegar, truffles, gelati, cheese and prosciutto on this exploration of Bologna, Modena and Parma. You’ll get away from the main tourist trail and pedal quiet roads, enjoying behind-the-scenes visits of parmesan cheese and balsamic vinegar producers. By day, visit ancient castles and UNESCO World Heritage Sites, before returning to your beautiful accommodation, which includes an agriturismo – a country house hotel with a working farm.

Start in Bologna, known for its long tradition of studies, arts, and gastronomy. Enjoy stunning views on the ‘rails-to-trails’ bike path that follows the old railway track to the fortress town of Bazzano, before heading on to magnificent Modena. A steady pace will burn off most of the calories gained from savouring the abundant regional delights. The sights, including fortress town Bozzano and the fifteenth century Torrechiara Castle, more than match the culinary experiences. After leisurely days in the saddle, refuel with gourmet evening meals that will include some of the finest traditional cuisine in the world. This Italy cycling weekend is a must for wine lovers and gourmands.


Experience Bologna to Parma through a stunning region of Italy where history, art, culture combine with fantastic food to deliver the unforgettable Flavours of Emilia Romagna.

Emilia Romagna cycling holidays
Tuscany Cycling Holidays

For more recommendations on the best destinations for your Italy cycling weekend, give us a call on 020 7471 7760.

We Can Tailor-make
a Holiday to Suit You…

We have a team of experts on hand to help you choose the perfect holiday. From a luxury cycling holiday weekend in Tuscany to a big adventure in through the Loire Valley, we’re whatever you want your holiday to be.