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Cycling Holidays in Italy

It’s no surprise that Italy has produced some of the world’s greatest artworks and a host of respected artists, the country is truly inspiring. From ancient Roman ruins and diverse landscapes to delicious cuisine and passionate locals, every aspect of a holiday in Italy is enchanting.

The highlight for many is the food and wine. Local dishes vary throughout the country; the cuisine is heartier in the north and more Mediterranean along the Amalfi coast. Visit the wineries of Chianti in Tuscany, see how Parmesan cheese is made in Parma and balsamic in Modena. 

Cycle through vineyards and olive groves, delve into the Renaissance art scene and take in the spectacular countryside. Our e-bikes are a great way to get around the hilltop towns in Tuscany and Umbria, as well as enabling you to travel further without getting too tired.

What's included?

  • Delicious restaurant meals each night
  • Bed & breakfast accommodation
  • Unrivalled on the ground assistance
  • Luggage carried between your hotels
  • Fully serviced bikes, option to e-bike
  • ABTA & ATOL protected
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George, Cycle Expert

Rolling hills stretch as far as the eye can see in Tuscany, crowned with hilltop villages. In between cycles, play the connoisseur at a Prosecco or wine tasting, admire the towering peaks of the Dolomites or taste the regions finest delicacies on a Softies holiday.

Cycling in Italy

Take in the postcard-perfect views of vine-covered valleys, hilltop villages, cypress-lined Roman roads and the shores of Lake Garda's emerald waters on a cycling holiday in Italy. Have a break when you reach historical sights, scenic viewpoints and wineries, olive oil farms or local delicacy tastings.


We have e-bikes for those that would rather conserve their energy for exploring churches, monasteries and sweet villages. Electric bikes offer battery-powered assistance to help you up inclines or allow you to travel further distances.

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Italian cuisine and wine

Our favourite aspect of Italian cuisine is cucina di nonna – the tried and tested recipes passed down through generations of Italians. A common misconception is that Italian cuisine revolves around pizza and pasta when it is centred around meat, fish and vegetables.


After exploring the area by bike, start your meal with a small plate of pasta. Then try the fresh seasonal ingredients of vegetables, seafood, meat and grains with a generous douse of olive oil. The full-bodied Chianti red wine is a perfect accompaniment to any dish.

When to visit

Our tours run between April and October, which tend to be the drier and warmer months. We can tailor your trip so you aren’t cycling during the heat of the day and still see the sights.

Historical sights

Dating back to the 6th and 7th century, the ancient Roman ruins of Pompeii at the foot of Mount Vesuvius are an absolute must-see in Campania as you cycle along the Amalfi Coast. Once the capital of the Western Roman Empire, Ravenna is home to Dante’s tomb, Sant’Apollinare Nuovo and the UNESCO-listed mosaics of San Vitale.


In Venice, admire the city’s Gothic architecture from a gondola as you weave along the city’s canals. Delve into the Renaissance masterpieces in Florence’s Uffizi, the incredibly lavish Pitti Palace and the 360-degree view from the bell tower of Santa Maria del Fiore.

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Our insider tips

  • Taste dry, medium-bodied Chianti wines at local wineries while you learn about the grape harvest and wine production.


  • Cycle around the stunning lakes of northern Italy – Lake Trasimo and Lake Garda are our favourites – then park your bicycle up for a picnic on the shore.


  • Learn to make home-made pasta in Umbria with Gianna, who is an expert in old fashioned Italian home cooking.

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