Our cycling holidays in Italy
Cycling and Italy feel intrinsically linked, with so many divine landscapes made for exploring by bike from Puglia to the Dolomites, Sicily, Amalfi, Umbria and Tuscany. Guided small group trips offer a sociable and motivational atmosphere, while self-guided holidays give you the freedom to do your own thing. And relish the experience of staying in locally owned accommodations throughout, which will sometimes even offer home cookery lessons, a delicious way to explore Italian culture further still. You’ll cycle through areas that see relatively little tourism, so your stay (and healthy appetite) helps traditional communities and ways of life to survive.
Our top Cycling holidays in Italy
Sicily self guided cycling holiday in Italy
From
£1729 to £1949
9 days
ex flights
A wonderful introduction to baroque Sicily's south-east
Tailor made
Puglia self guided cycling tour
From
£1449 to £1884
8 days
ex flights
Eight day idyllic journey around the Puglia
Tailor made
Umbria self guided cycling holiday, Italy
From
€1300 to €3500
7 days
ex flights
Easy cycling across ancient towns and vineyards
Tailor made
Cycling holiday across Italy, Puglia to Sorrento
From
£3729
8 days
ex flights
Ride across the boot of Italy
Small group
Cilento and Amalfi cycling holiday, Italy
From
£2465 to £2805
9 days
ex flights
Colourful towns & lemon groves on the Amalfi
Tailor made
Piedmont cycling holiday, Italy
From
£2319 to £2749
9 days
ex flights
Gastronomy, rolling hills & sun drenched hamlets
Tailor made
Sicily cycling holiday in Italy
From
£1969 to £2369
8 days
ex flights
Sicily's UNESCO sites of Siracusa, Noto, Modica and Ragusa
Small group2026: 27 Sep, 4 Oct, 18 Oct, 2027: 11 Apr, 25 Apr, 2 May, 16 May, 23 May, 30 May, 20 Jun, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct
Highlights of Puglia cycling holiday
From
£1879 to £1999
11 days
inc UK flights
Explore Italy's beautiful, sun-drenched Puglia region
Tailor made
Puglia cycling holiday in Italy
From
£1955 to £1995
8 days
ex flights
Discover the 'heel' of Italy on easy cycle rides
Small group2027: 25 Apr, 9 May, 16 May, 23 May, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 17 Oct
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More about our cycling holidays in Italy
Self guided or small group holidays?
Cycling in Italy offers you a choice of either self guided tailor made trips where you have plenty of flexibility on your itinerary, or small group tours where you’ll be accompanied by a guide throughout. While both have their advantages, if you’re new to cycling in Italy a small group tour is a great way to try out routes with all the logistics taken care of for you, and with a supportive, sociable bunch of riders to cheer each other on. Whichever you opt for, you’ll have a wide choice of locations, and you can be confident the routes have been honed to perfection.
Amalfi Coast cycling holiday in Italy
Feted for its glitz and glamour, Italy’s Amalfi Coast also has a sterling reputation for providing cyclists with some of the most scenic coastal rides in Europe. Highlights include long, winding descents on the Strada Statale and the fishing villages and clifftop tracks of Cilento National Park. You’ll need to hold your nerve on some of the steeper sections, and July and August are best avoided if you don’t want to navigate roads cluttered with sightseeing coaches. But just a short distance from the main coastal strip you’ll find traditional life going on as it has for centuries in blissful tranquillity.
Puglia cycling holiday in Italy
The heel of Italy’s boot is flat, dry and sunny, and ideal for cyclists looking for easy-going rides amid beautiful scenery a long way from the main tourism destinations. Puglia has two coastlines – the Adriatic and the Ionian – providing plenty of spots to pull over for a dip, so bringing a swimsuit with you every day is a smart move. Late spring and early autumn are the best times of year to cycle in Puglia, while quiet roads with unchallenging gradients make this a great region to try out self guided holidays. Small, locally owned B&Bs in sleepy seaside villages welcome you every afternoon.
Sardinia cycling holiday in Italy
The windswept Costa Verde and white beaches of the Costa del Sud make Sardinia an idyllic place for cycling holidays. Two-wheel travel is the perfect way to explore the island’s natural beauty accompanied by an invigorating sea breeze. Skip the overpriced and overcrowded Costa Smeralda in favour of wetlands where flamingos strut their stuff, quiet fishing villages and pine woods populated with deer. Small group tours are led by guides as adept at stringing together Sardinia’s history through its ancient sites as they are at pointing out the best place to find seafood linguini at the end of the ride.
Dolomites cycling holidays, Italy
There are few more dramatic backdrops for Italian cycling holidays than the classic cols and alpine routes of the Dolomites. But it’s not all calf-straining climbs here; there are plenty of more leisurely routes taking you along riverside tracks, through fruit orchards and pausing at vineyards. For a cultural treat, consider a trip that descends from the Dolomites to Lake Garda, and then to Verona and Venice. Or a centre-based tour on purpose-built cycling roads, quiet lanes and old railway tracks through illuminated tunnels – and with a spa hotel waiting for you on your return.
Our Cycling holidays in Italy reviews
4.6
45Cycling holidays in Italy reviews
Dana Tupy11 Jul 2026
It was great vacation. Beautiful memories.read more
Denise Jones21 May 2026
Excellent bikes beautiful scenery and appropriate trip times each day. 5 stars.read more
Jacqui Pickles08 May 2026
Excellent. Loved that we got to visit so many remote places - support excellent. 5 stars.read more
