Cycling Holidays in Italy

Our expert local guides know the scenic backroads, the best viewpoints, and the quieter ways into even the busiest spots. With perfectly paced routes and charming stays, this is Italy by bike as few ever experience it. We know just where to pause for the best view of the rolling lemon groves and glittering bays – and the perfect photo stops with friends, old and new.

Yes. All our Italian cycling trips are small group tours with 5 to 16 people , so you’ll enjoy a sociable yet personal feel throughout. Whether you choose an e-bike adventure or a traditional road cycling trip, our guides know how to adjust a derailleur, recommend the best post-ride spritz, and explain the history of a ruined monastery – in one breath.

Most of our cycling holidays in Italy are graded Moderate (Activity Level 3), ideal for those with a decent base fitness. Expect a mix of flat, hilly, and occasionally demanding terrain, with distances averaging 30 to 37 miles (50 to 60km) per day. For example:

• Cycling Puglia & Matera: Mostly paved roads with two hilly days, plus time to explore UNESCO-listed towns like Matera and Alberobello.
• Cycling in Sicily: Rolling countryside, coastal climbs and flat stages, plus optional dips in the sea to cool off.
• Cycling in Sardinia: A blend of scenic coastlines and inland hills, with some gravel and sandy sections to keep things interesting.
• Cycle Cilento & Amalfi Coast: Undulating routes, longer climbs, and thrilling descents, with views that reward every uphill.

E-bike options are available on many tours for those wanting extra support. Read more about our activity levels for cycling trips.

Absolutely. Many of our cyclists travel solo, and our small group format is ideal for sharing the road and the ride with like-minded people.

Cycling in Italy is a carefully designed blend of landscape, culture and connection. Some favourites include cycling from Puglia to Amalfi Coast on an e-bike,
crossing the country from the cave dwellings of Matera to the clifftop villages of Amalfi. Cycling in Sardinia leads you past flamingo-filled wetlands, ancient Phoenician ruins, and gleaming beaches like Portixeddu. On Cycle Cilento & Amalfi Coast, you’ll ride to 2,500-year-old Paestum and follow one of the world’s most scenic coastal roads. Cycling in Sicily takes you through the baroque jewels of the Val di Noto, past citrus groves and canyon landscapes. But the real highlights happen apres-cycle: the shared dinners and drinks, the sneaky ocean dips and the swopping of numbers of new friends from all over the world.

Always. We like to think they’re baked in like a good focaccia. You might wander the whitewashed alleys of Ostuni before dinner, visit an olive oil mill in Puglia, or stand among ancient Greek columns at Paestum. Local cuisine, family-run wineries, and traditional cooking (or chocolate tastings in Modica) form the heart of each day. One traveller shared: “The cave room, the trulli stay, the Masseria with its own wine and oil, the morning swim in Otranto — every stop had a story.”

We carefully choose each route for its wow-factor – and some surprises along the way. Our tours explore a mix of Italy’s most spectacular and lesser-known regions, from the heel to the toe, the coast to the hills. In southern Italy, you might ride across Puglia, with its trulli-roofed villages like Alberobello and stone city of Matera. On the island of Sicily, you’ll pedal through the baroque towns of Modica and Noto, with ample photo stops among the citrus groves. In the southwest corner, Sardinia’s Costa Verde offers a wild landscape of dunes, Phoenician ruins and sea breezes. Meanwhile, the Cilento and Amalfi Coast, south of Naples, rewards riders with more than just great drinks spots – vineyard-covered hills, sparkling bays and ancient temples.

We choose stays that add local flavour to every ride – and not just at mealtimes. In Puglia, Masseria Bosco offers vaulted ceilings, a cooling pool and olive grove views, while Sicily’s Feudo Bauly surrounds you with heritage and home-cooked dishes from the Corsino family. On the Cilento Coast, Agriturismo Zio Cristoforo serves up rustic charm and in Palinuro, you might check in at Santa Caterina – home to the town’s oldest ice cream shop. It’s rest, reward and regional flair – rolled into one.

Yes, and they’re a game-changer. Our Italy Coast to Coast by E-bike tour lets you cross from the Adriatic to the Tyrrhenian without breaking a sweat (unless you want to). You’ll still earn your views – like the cinematic arrival in Sorrento – but with a little extra power on the climbs. Prefer pedal power? Ask our team about standard road bikes.

Spring (April to June) and autumn (September to October) are ideal. You’ll enjoy warm temperatures, quiet roads, and landscapes in full bloom or golden glow. Summer brings the heat, great for coastal dips and longer days, but perhaps a little sweatier inland. Whatever the season, we’ve timed our cycling tours to make the most of it.