Cycling Holiday Sicily

Explore Sicily’s Scenic Routes and Different Cultures on Two Wheels

Mountain Illustration displaying a cycling tour difficulty rating of nine out of ten

Overview of Our Best of Sicily Cycling Holidays

Sicily is both a distinct land and culture; a land of wild natural beauty, breathtaking wonders, and extraordinary architecture; and a culture shaped by a patchwork of different civilizations and cultures dating back to the Phoenicians, Greeks, and Romans. Steeped in history and tradition, the unique identity of Sicily is at the very heart of our cycling adventure, both on and off the bike.

Ancient cultures have left their mark on the architecture, language, and cuisine, however today the Sicilian culture and way of life is very much Italian. It is a culture filled with warmth and passion for all things Sicilian first and Italian second – and captivates you in so many different ways as you traverse its deep agricultural heart, and take in the scenes around every windswept turn and up every rock-walled climb of what often feels like a forgotten land in Southern Italy.

Traveling coast to coast, and from west to east, expect beautiful Spring days on daily rides that take you across the stunning and diverse landscape; from the sea to the mountains, and across the rugged hills, rolling farmlands, and wildflower lined backroads in-between.

You’ll ride your bicycle through countless beautiful villages and towns dotted across the landscape, including the captivating towns of Ragusa, Caltagirone, and Palazzolo Acreide, known for their stunning baroque architecture; navigate delightful seaside towns from Trapani to Siracusa and San Vito to Avola; and find yourself immersed in the enchanting and timeless piazzas of Ortigia and Taormina. Many of these towns, such as Palazzolo Acreide, are recognized as UNESCO World Heritage Sites, highlighting their cultural and historical significance. You’ll also spin past olive trees and pistachio groves, orange orchards and green-hued vineyards, ancient Roman hilltop villages, fields filled with black lava rocks, and Greek temples that have been standing for 2500 years. Your cycling adventure will culminate in a challenging ascent of Mt. Etna, the largest active volcano, followed by a rewarding 50km downhill journey.

Our Sicily bike tour is a true adventure; a feast for your senses where every day delivers unexpected vistas, a journey through the distinctive and diverse food and wine cultures of the island, a multitude of unique Southern Italian tastes, and a level of interaction with the locals that only Sicily’s distinct and warm, open-hearted people offer.

Over 10 days, you’ll experience a taste of the best that Sicily has to offer.

Get ready for the adventure of a lifetime – both on and off the bike.

Sicily Cycling Itinerary

Experience cycling in Sicily, Italy.

Our daily rides through Sicily ensure you experience the diverse landscapes it has to offer, from the turquoise seas along coastal roads, through the ancient ruins, olive groves, and citrus orchards, up beautiful climbs to mountains of volcanic rock and to towns with their own mark on the ancient history of Italy. You’ll definitely enjoy cycling through Sicily, Italy, with its wild beauty and stunning, rugged landscapes, and finishing each day’s ride with time to relax and enjoy the beautiful places we stay.

An utterly spectacular start with a beautiful climb up to discover a charming and ancient Roman hilltop village. This will give you the opportunity to make micro adjustments to your bike fitting as you stretch the legs after your travels

Highlight: The vista of the rugged mountain toward San Vito Lo Capo from the hairpin corners.
Distance: 38.2km
Elevation: 819m

Rolling out of our seaside village, we hug the coastline before heading into the rock-strewn rugged hills and through quiet villages on our way to one of Sicily’s iconic seaside spots

Highlight: The contrast of the vivid turquoise waters against the rugged backdrop.
Distance: 86.9km
Elevation: 981m

We will start the day with a short transfer in the van to our start location. From there we’ll proceed around the Sicani mountains and beautiful arid country dotted with olive groves as far as the eye can see, before changing tact and heading for the Valley of Temples.

Highlight: Rolling past Greek temples that have been standing for 2500 years.
Distance: 101.9km
Elevation: 1686m

An undulating day through the agricultural heart of Sicily on our way to Caltagirone and then on to our Masseria. We’ll wind our way through a landscape of open golden fields, patches of olive groves, roads lined with spring wildflowers and cacti, and punctuated with small villages and hills.

Highlight: The landscape’s golden vastness and silence.
Distance: 83.1km
Elevation: 1499m

A beautiful undulating loop taking in the surrounding hills and the picturesque villages below, with a mix of open roads and hairpin-laden descents, provides a day that is a feast for your senses. Gravel bikes are perfect for these diverse terrains, offering a thrilling adventure through Sicily’s scenic beauty.

Highlight: The rugged landscape in what feels at times like a forgotten land.
Distance: 95.4km
Elevation: 1546m

A seriously sensational day on the quiet rock-wall-lined roads as you traverse the eastern part of the coastal route through the Iblei mountains and the beautiful baroque towns that sit atop them.

Highlight: The vista of the final km as we roll into our hilltop village for the night.
Distance: 104.1km
Elevation: 1264m

You’ll awaken to the sounds of the sea and after a leisurely breakfast, we’ll start with a flat spin past small beaches, national wildlife and natural reserves, and views of Ortigia from the East & West and Greek ruins and all before our mid-ride espresso.

Highlight: The continual view of Mt Etna through the changing landscapes.
Distance: 44.4km
Elevation: 338m

A short 75 minute transfer to our start location. From here we’ll ride around Mt Etna volcano, with the gentle giant always visible over our shoulder. We’ll roll through orange orchards, pistachio groves, the black lunar landscapes from previous lava flows and past ancient hilltop towns, before a final 10km descent into our stunning mountain-side resort

Highlight: The continual view of Mt Etna through the changing landscapes.
Distance: 68.5km
Elevation: 1952m

The pinnacle of the tour is where we’ll tackle the gentle giant Etna volcano. We’ll ease into the ascent and steadily climb for the first 27km through forests and old lava flows, before reaching the rifugio at the road’s end. Enjoy the view as we take in some refreshments before we have an utterly amazing descent back to our volcano-side hotel

Highlight: A 30+km descent!
Distance: 76.6km
Elevation: 1945m

Sicily Bike Tour Pricing & Dates

8995
per person twin share / Maximum 14 guests

Show Price As

2025

10th to 19th May 2025 – 3 Places Available

1995
(deposit)

2026

13th to 22nd May 2026

1995
(deposit)

Want to enjoy cycling in Sicily, Italy, on your very own tour? Ask us about a privately run tour for your group.

Start Location & Details

City: Palermo, Italy
Pick Up Location: Piazza Verdi
Pick Up Time: 11:00am

Finish Location & Details

City: Catania, Italy
Drop Off Location:
Taormina or Catania-Fontanarossa Airport
Drop Off Time: 11:00am

Sicily Bike Tour Inclusions & Details

Accommodation & Meals

A rider getting their hire bike adjusted on a Italian cycling holiday

Ride Support

Transfers & Activities

Two piece italian made cycling kit

Ride Kit

Not Included

Bike Hire & Gear

Carbon Road Bike with Electronic Shifting

You can choose to hire a Wilier Cento 10SL carbon road bike with Sram Rival Etap, a compact crankset, with a 32 rear cassette & disc brakes.

Carbon Road Bike with Mechanical Shifting

You can choose to hire a Bianchi Sprint bike with a mechanical Shimano Ultegra groupset, a compact crankset, with a 32 rear cassette & disc brakes.

Non-Riding Partners

As part of our cycling holiday in Sicily, non-riding partners enjoy an active and dedicated travel program, designed to deliver a diverse range of activities and the best experiences Sicily has to offer. Whether it’s beautiful hikes in national parks and on Mt Etna, guided walks of historic towns and their unique architecture including the medieval old town, of Erice, or the maze-like, narrow streets, and expansive piazzas of Ortigia, or exploring olive groves and enjoying private olive oil tastings and cooking classes, non-riding partners experience the beauty and uniqueness of each area we visit. With an itinerary curated by Nancy and delivered together with a range of partners and guides whom she personally selects. It’s sure to be a holiday in Sicily you’ll never forget.

As our non-riding partner program is an active adventure, there is a minimum walking requirement for non-riding guests for each tour. Please enquire when booking.

Sicily Cycling Tour Accommodation

Enjoy our personally and carefully selected range of authentic Sicilian accommodation. From staying in an architecturally restored Masseria with a ‘window’ overlooking ancient sites, beautiful seaside villas with views over turquoise seas, historic locanda’s in the old town, and in the quiet countryside where family run farms are still producing wine and olive oil, this diverse experience brings together the beauty of ancient, historic Sicily with the rustic, modern and sometimes chic Sicily.

Food & Wine

Cannolo, Caponata, Pistachio Gelato, and Pesce Spada; Sicilian classics are always on the menu. We’ll sample these tastes and a whole lot more as we venture further and deeper into the diverse Sicilian cuisine. We’ll delve into the very local specialties and grape varieties of every region in which we stay, and dine in a diverse range of settings as we sample a wide range of flavors. Of course, we’ll start with seafood, either “crudo”, cooked on charcoal, or in the sweet and sour “agrodolce” and progress through the specialty pasta of each region, with a long list of local ingredients that are often only grown in the rich volcanic soils of Sicily, or in the warm Tyrrhenian seas surrounding the island – from local sardines and prawns, to pistachios and almonds, carciofi, wild fennel and pomodori daterini, and of course the famous Sicilian citrus – we’ll enjoy a full seasonal menu on our Spring tasting adventure.

You’ll try some wines that you may not have had before – including Etna Bianco, Insolia, Grillo, and Catarratto. Frappato, Perricone – and some that you may have, including Nero d’Avola and the sensational Etna Rosso.

Our food and wine experience in Sicily will feel like a tour within the tour.

Testimonials

Frequently Asked Questions

Our route directions are meticulously planned, providing you with turn-by-turn comfort and safety. You’ll also have access to GPS files on tour to support your guided rides throughout your cycling adventure.
The routes are designed to cater to experienced riders, with options to ride sections of our more challenging rides. Our guides will provide support, and we can adjust the difficulty of each day’s ride as required.
We provide detailed pre-trip information, including tips on what to pack and how to prepare for Sicily’s diverse terrain. Our team is also available to answer any specific questions you may have before your departure.
Sicily is a melting pot of cultures, and on this trip, you’ll explore its rich history influenced by Greek, Roman, Arab, and Norman civilizations. From architecture to cuisine, you’ll experience a variety of cultural delights.
The best time for a cycling holiday in Sicily is during the spring (April to early June) and autumn (late September to October). These seasons offer milder weather, making it ideal for cycling and exploring the island’s diverse cultures and landscapes.

Have More Questions About Our Sicily Cycling Tour?

Check out our FAQ section.

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