Cycling holidays in Italy

We are passionate about Italy as a cycling holiday destination and have selected cycling holidays that showcase the varied nature of the country. For cycling holidays in Italy, Freewheel has 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 nearby 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 options and luggage transfers. Optional extras such as half board and E-bikes are available for a surcharge.

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Featured Trip

Ride along the Tuscan coast from the Leaning Tower of Pisa to Elba on this self-guided holiday. Combine the hilly landscape of Tuscany with the Etruscan coastline as you follow the vineyards and olive trees to the coast. A real highlight of the trip is the Isle of Elba, the place of Napoleon’s exile.

With picturesque trails winding through national parks, olive groves and vineyards and a host of cultural attractions, this is an unforgettable holiday!

Price range

£3000

26 Results found

Ljubljana to Piran – Emerald Route
Calender 8 days

Difficulty: Leisurely

Merano to Lake Garda
Calender 7 days

Difficulty: Leisurely

North Sardinia
Calender 8 days

Difficulty: Moderate

Parenzana Trail
Calender 5 days

Difficulty: Moderate

Piedmont Round Trip
Calender 8 days

Difficulty: Challenging

Pisa to Florence
Calender 7 days

Difficulty: Moderate

Turin to San Remo
Calender 8 days

Difficulty: Moderate

Tuscany Coastline
Calender 7 days

Difficulty: Challenging

Venetian Highlights Plus
Calender 8 days

Difficulty: Moderate

Venice to Florence
Calender 8 days

Difficulty: Moderate

Venice to Poreč
Calender 8 days

Difficulty: Leisurely

GOT ANY QUEStions?

call 01706 618155 for all bookings and enquiries

We have officially merged Wheel2Wheel Holidays into Freewheel Holidays. If you have been redirected from a search engine result, welcome to Freewheel Holidays!

You’ll still find similar cycling holidays to the product range as previously displayed on Wheel2Wheel Holidays. However, if you cannot see what you are looking for, please contact us.