Cycling holidays in Italy

We are really passionate about Italy as a cycling holiday destination and have selected cycling holidays that really showcase the varied nature of the country. For cycling holidays in Italy, Freewheel have the whole country covered, from the Dolomites in the north to cycling holidays in Sicily in the south.

You'll ride around wonderful cities like Venice, Florence and Verona, and also enjoy the remarkable scenery of rural Tuscany, Sicily and Sardinia on your bike. For something a bit different why not try our popular ‘Boat & Bike’ holiday between Venice and Mantova, or follow the Adriatic coast from Venice round to Porec in neaby Croatia? The islands of Sicily and Sardinia offer a great off-season choice for early or late in the year sunshine.

We have selected cycle tours with convenient starting points to make joining your cycling holiday as simple as possible. Many of the cycling holidays in Italy start close to main airports such as Milan, Pisa or Venice for ease.

You then transfer by local transport to the starting point of your cycle tour in Italy. We advise you on how to do this.

All cycling holidays in Italy include at least B&B accommodation, maps, route guide, bike hire and luggage transfers. Optional extras such as half board and E-bikes are available for a surcharge.

Milan to Lake Como Short Break

Beginning in the city of Milan, capital of Lombardy, you will soon immerse yourself in the unexpecte..

  • 4 Days
  • Easy
  • Families
  • Self-Guided
  • Lakes-rivers-canals
  • E-Bikes Available
View Holiday

Montecatini Terme to Florence

Cycle from Montecatini Terme to Florence on this unforgettable self-guided tour through Italy. Ride ..

  • 8 Days
  • Challenging
  • Self-Guided
  • Historic
  • E-Bikes Available
View Holiday

North Sardinia

Explore the northern part of Sardinia from Olbia to Alghero on this self-guided holiday. With breath..

  • 8 Days
  • Medium
  • E-Bikes Available
  • Self-Guided
View Holiday

Piedmont

Pure indulgence lures gourmets worldwide to this large mountainous region of Italy. In the Piedmont..

  • 8 Days
  • Challenging
  • E-Bikes Available
  • Self-Guided
View Holiday

Pisa to Florence

The landscape of Tuscany is one of the most beautiful in Europe, with rolling hills laced with verda..

  • 8 Days
  • Medium
  • Self-Guided
  • City
  • E-Bikes Available
View Holiday

Pisa to Siena (Via Francigena)

From Pisa, with its imposing tower and its magnificent baptistery, this tour will take you along&nbs..

  • 7 Days
  • Medium
  • E-Bikes Available
  • Self-Guided
View Holiday

Sardinia Short Break

Three days plunged into the savage, romantic beauty of south west Sardinia, amongst abandoned mines ..

  • 5 Days
  • Easy
  • E-Bikes Available
  • Self-Guided
View Holiday

Sicily Adventure

Explore the south east of Sicily, the largest Mediterranean island. You will cycle through the..

  • 8 Days
  • Medium
  • E-Bikes Available
  • Self-Guided
View Holiday

Siena, Chianti and Florence

The landscape of Tuscany is one of the most beautiful and evocative in Europe, with rolling hills la..

  • 8 Days
  • Medium
  • E-Bikes Available
  • Self-Guided
View Holiday

Turin and Piedmont

Discover a different side to the Piedmont region on this self-guided cycling holiday. Cycle along th..

  • 8 Days
  • Challenging
  • E-Bikes Available
  • Self-Guided
View Holiday

Turin to San Remo

Just like the famous cycle route from Milan to San Remo, this glorious bike tour takes you from the ..

  • 8 Days
  • Easy
  • E-Bikes Available
  • Self-Guided
View Holiday

Tuscany - One Hotel

Explore Tuscany by bike on this self-guided holiday in Italy. Each day’s cycling begins from t..

  • 8 Days
  • Medium
  • E-Bikes Available
  • Self-Guided
View Holiday

Tuscany Coast and Elba

Ride along the Tuscan coast from the leaning tower of Pisa to Elba on this self-guided holiday. Comb..

  • 7 Days
  • Challenging
  • E-Bikes Available
  • Self-Guided
View Holiday

Tuscany Hills - Road Bike

An unforgettable tour that takes in the Tuscan countryside and its most beautiful cities. Florence, ..

  • 8 Days
  • Extreme
  • Self-Guided
View Holiday

Umbria and Perugia

Cycling this magical landscape and among the gently rolling hills of Umbria you will find many conve..

  • 8 Days
  • Medium
  • E-Bikes Available
  • Self-Guided
View Holiday