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Self Guided 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.

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Secrets of Sicily Cycling
Italy: Sicily

Secrets of Sicily Cycling

Explore the undiscovered western coast of Sicily by bike to find pristine nature reserves, ancient monuments and Baroque towns. Highlights include Segesta's amphitheatre and Selinunte Archeaological Park.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MR
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2360per person, tour only

  • 20 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling through Baroque Sicily
Italy: Sicily

Cycling through Baroque Sicily

This eight-night, self-guided cycling holiday provides a wonderful introduction to Sicily's south east, a part of the island renowned for its beautiful, unspoilt coastline, spectacular Baroque architecture and sumptuous regional cuisine.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08BS
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3200per person, tour only

  • 18 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)

Frequently asked questions

Is Sicily good for cycling?

Absolutely. Sicily is one of the best locations in Europe to experience on two wheels.

Why? An ideal climate in the months either side of summer make it a wonderful spring or autumn getaway. The hilly, mountainous landscapes filled with ancient Greek, Roman and 17th century Baroque architecture, scrumptious Sicilian cuisine, and an unspoilt coastline make it a truly unforgettable spot to visit.

Which area of Sicily is best for cycling?

The sensational landscapes and terrains of Sicily make it a cyclist's paradise no matter where you head, but many repeat visitors to the island certainly have their favourites. Palermo in the west is Sicily's central hub and also a font of Baroque architecture. And Noto, found at the very tip of the southeast coast in Syracuse, is rife with architectural and academic history among many great cycling trails.

Rest assured, our cycling tours of Sicily take in some of the very best areas the island has to offer.

How long does it take to cycle around Sicily?

Taking on the entirety of Sicily by bike would be a wonderful but rather mammoth challenge. So, we've created weeklong-plus packages that focus on a specific region of the island and the best parts within it. You can spend seven nights on the west coast or eight nights in the southeast Baroque region, and in that time we're confident you'll see everything you want while enjoying a relaxing tempo to your trip.

How do I book a Sicily cycling holiday?

There are four ways to start your Sicily cycling tour booking with us:

What to pack for a cycling holiday in Sicily?

Your packing list for a cycling holiday in Sicily should be centred around the typical clothing and equipment you would take for a warm weather cycling excursion. With that said, it's always worth packing for colder and wetter weather too, just in case. You should also check on the activity level of your chosen trip and make sure you have all the supplies and support equipment to meet your needs across your travels.

Bear in mind that we take care of the bike hire for you, and that Sicily is geared towards cyclists and cycling tourism. So, if you do happen to forget anything, you will likely be able to find it during your trip.

What time of year is best for a cycling holiday in Sicily?

The annual window for cycling in Sicily is relatively broad, but even the most hardened cyclists will usually steer clear of the island's hottest conditions across the peak summer months of July and August. To enjoy a more moderate, but still beautifully balmy climate, we'd recommend visiting in spring, early summer or autumn – and that's exactly when you can book both of our bike tours of Sicily.

Why choose Headwater for cycling tours in Sicily?

You can trust us to deliver when it comes to making your Sicily cycling tour the trip of a lifetime. Our 40-plus years of experience in creating handpicked adventure holidays make us one of the UK's industry experts, and we're passionate about making your trip the best it can possibly be.

  • The best locations, carefully chosen - We tailor every detail of our tours to ensure we're providing you with the best possible experience of the area.

  • Highly rated - Don't just take our word for it. Take a look at our reviews on Feefo to see why our customers love our products and our customer service.

  • We take care of the logistics for you - Booking a cycling tour in Sicily comes with an awful lot of administrative responsibility, but not when you book with Headwater. We take care of all the logistics of your trip, from accommodation and flights through to navigation, bike hire and luggage transfer, so you can focus on enjoying every moment of your time away.

  • Award winners - We're proud to have won at the British Travel Awards 2022.

  • Green minded - We're keen to be as sustainably focused as possible. Take a look at our People, Places, & Planet Plan and Nature Net Positive initiative to see how we're looking to combat climate change.

  • ABTA- and ATOL-protected - Your cycling holiday in Sicily is both ABTA and ATOL protected, so you can book with absolute confidence. Find out what your key rights are when booking a holiday with us.

  • Community driven - We love all of the locations we provide self-guided tours to, from our cycling tours of Sicily through to our adventures all across Europe. With that in mind, we want the areas we cover to benefit from the incoming tourism, which is why we established the Exodus Travels Foundation to empower and protect the communities and environments that our customers visit.

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