Cycling Holidays in Sicily

Our self guided cycling holidays in Sicily are based on the west coast and south-east of the region, encapsulating beautiful coastlines, spectacular Baroque architecture, and sumptuous regional cuisine. With fantastic, hand-picked hotels and your luggage transported for you, everything is organised so that you can simply focus on your stunning surroundings and enjoy your cycling holiday in Sicily to the full.

Enjoy plenty of the famous TV detective Inspector Montalbano's favourite haunts, including atmospheric Scicli, and in-between pedalling through towns and old fishing villages, savour a fresh fish lunch in the salty sharp air, admire ornate cobbled streets, and discover nature reserves and saltwater lagoons, rich in birdlife.

Let us help you book your dream self-guided Sicily cycling tour

Ready to discover the very best cycling trails Sicily has to offer? With Headwater, you can book a self-guided cycling holiday of the region with ease - and we'll take care of all the logistics for you. Start your booking today or, if you have any questions, get in touch with us and a member of the team will be happy to help.

Where can I visit on a Sicily cycling tour?

Our cycling tours of Sicily offer routes that incorporate stunning coastlines, ancient ruins, exceptional food stops and the best of the island's traditional architecture. Here are a few of the things you can see on a trip with us.

Southeast Sicily

Opt for our cycling tour of Baroque Sicily and you'll enjoy an eight-night stay in one of the island's most culturally diverse regions. The lower right corner of Sicily is ripe with Roman and Greek architecture, with the city of Syracuse - a place Cicero once considered the most beautiful of all Greek cities - one of the highlights. Across southeast Sicily, you'll see a stunning portfolio of Baroque architecture, unscathed natural coastline and be spoilt with some of the best food around.

The west coast

Western Sicily is home to the island's economic and tourist capital in Palermo, but much of the west coast remains largely untouched and undiscovered. Our cycling holidays in western Sicily look to uncover the secrets behind this historically rich region. See the famous 3rd century BC temple at Segesta, and marvel at over two-and-a-half millennia of history at Selinunte Archaeological Park.