Self Guided Walking Holidays & Cycling Holidays


Cycling in Italy

All Cycling in Italy

Cycling Holidays in Italy

Italy is one of the great biking cultures. With a range of landscapes from the mountainous regions of the north, where the roads snake their way up and over mountain passes to the roads that wind their way along the Mediterranean or Adriatic coasts there are plenty of options for cyclists. Browse our full range of cycling holidays in Italy. 

You can cycle in Tuscany, from Pisa to Florence or explore Tuscany's little-known neighbour cycling in Umbria. You can take in waterways of Venice by Bike & Boat, or the beautiful coastlines of Puglia. All of our self guided cycling holidays in Italy include hand-picked accommodation, baggage transfer, detailed information packs and emergency support. All you have to do is cycle, eat, relax and repeat.

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Cycle The Highlights of Puglia

Ride across the heel of Italy, cycling from the trulli houses of Alberobello to the Adriatic waters of Salento, relaxing each night in historic town houses and coastal hotels.

Duration: 9 days 8 Nights
Available: March to Mid-July & September to November
From £995

Tuscany: Pisa to Florence Cycling

Discover quintessential Tuscany on two wheels. From the world-famous city of Pisa and its iconic tower, you pedal through the Tuscan landscape, past scented vineyards and verdant olive groves towards Florence: birthplace of the Renaissance and city of timeless beauty.

Duration: 7 Days & 6 Nights
Available: March - November
From £535

Venice to Poreč

Cycle from Venice, along the Adriatic coast, to Poreč. Discover the delights of Venice, the Adriatic Coast, Trieste, coastal Slovenia, beautiful Istria and historic Poreč by bike.

Duration: 8 Days & 7 Nights
Available: April - October
From £595

Cycle Puglia In Style

Cycle Puglia, the heel of Italy, from the Adriatic waters of Monopoli to the UNESCO protected town of Alberobello. Spend each night in stylish comfort, including 2 nights in a lovingly restored trulli house, unique to Puglia.

Duration: 6 days 5 Nights
Available: March to Mid-July & September to November
From £895

Cycling Tuscany: Chianti & Siena

Experience the very best of classic Tuscany on a self guided cycle tour. Take to two wheels and cycle bella Italia, discovering picture-postcard Medieval and Renaissance hill-top villages as well as must-see Siena, accompanied by sumptuous cuisine and the famed Chianti, Brunello and Nobile wines.

Duration: 8 Days & 7 Nights
Available: March - Early November
From £995

Puglia: Cycle the Salento Coast

Discover Puglia, the heel of Italy, on this relaxed cycling tour of the Salento coastline.

Duration: 6 days 5 Nights
Available: March to Mid-July & September to November
From £625

Cycle Sicily's South

Discover the UNESCO listed Baroque towns and charming fishing villages of south east Sicily on this cycling tour of the ‘Val di Noto’.

Duration: 7 days 6 Nights
Available: March - October
From £795

Road Cycling: Florence to Siena

Ride from Florence to Siena through the heart of Tuscany’s Chianti postcard-perfect wine region.

Duration: 5 days 4 Nights
Available: May - October
From £505

Tour of Tuscany: Florence to Montepulciano

Take on our Tour of Tuscany cycling from Florence, through the world-class winelands of Chianti and Montepulciano.

Duration: 8 days 7 Nights
Available: May - October
From £985

Cycle Parma to Bologna

Discover the signature dishes and medieval towns of Emilia Romagna on this food lovers cycling tour from Parma to Bologna, spending each night in atmospheric, historic 4* hotels.

Duration: 8 days 7 Nights
Available: March - October
From £1,195
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