ENJOY A MIXED SELECTION OF WINE WHEN YOU BOOK IN MARCH*
 

Walking & Cycling Holidays in Sicily

Showing 5 out of 338 trips

Our activity holidays in Sicily are based in the undiscovered west of the region, rich in historical interest; the south-east of the region, famous for its UNESCO World Heritage towns, chocolate and wines; and the Aeolian Islands, the volcanic archipelago in the Tyrrhenian Sea north of Sicily.

The west is a former Arab kingdom, Palermo's Conca d'Oro (a ring of citrus groves) is an Arabian import. Many towns with their white-washed low walled square houses, such as Marettimo, would not look out of place in North Africa. The countryside is gentler here, than on Etna's flanks, characterised by sloping vine-terraced hills giving way to shingle coves and sandy bays lapped by sapphire waters.



The south has always been the preserve of the Spanish - Ragusa, Noto and Ispica were all rebuilt according to Spanish Baroque in the 17th century after an earthquake. Today their cathedrals could grace any Andalucian square. These gracious towns perch above dramatic limestone gorges, lined with oleander and carob trees. On the coast, you'll find miles of unspoilt, wide sandy beaches. Home to Europe's largest volcano, Mount Etna, this is a land of fertile terraces, bougainvillaea-decked squares and rocky volcanic shores, perfect for exploring on a gentle activity holiday.

The pristine western coast is a region of tranquillity, with azure waters and picture-perfect sandy coves. Just off Trapani lies the Egadi Islands, which are a true walkers' paradise. When walking in Sicily, you'll see a fantastic mix of volcanoes and interesting towns, and taste delicious local cuisine. If you're ready to plan your next adventure, feel free to contact our friendly team of experts today.

Where can I go walking in Sicily?

We've hand-picked some of the most picturesque and scenic routes for our Sicily walking holidays - look at some of the locations below:

Zingaro

Our Secrets of Sicily walking trail takes you to the Zingaro Nature Reserve, where you'll wind your way through the wild fennel, pomegranate, and citrus trees. You'll find amazing viewpoints which overlook the beautiful coastline, and the reserve is home to around 40 bird species - perfect if you're an avid bird watcher, and even if you're not, who can resist watching rare Bonelli eagles and other birds of prey on the wing?

Marettimo

Marettimo, the most remote of the three Egadi islands, is an ideal destination for those who want to learn more about Sicilian history and culture. See where the Romans and Carthaginians fought the First Punic War in the second century BC, and visit the 12th-century Norman Castello di Punta Troia. Don't miss the stunning whitewashed houses that dot the landscape against a backdrop of shimmering, turquoise waters.

Aeolian Islands

Book our Volcanoes of Sicily walk to island hop between the Aeolian Islands. Admire the spectacular Greek theatre of Taormina and visit Mount Etna, the largest active volcano in Europe. This Sicilian slice of paradise offers clear blue waters and volcanic beaches for those who fancy a refreshing swim en route

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.

READ MORE

Italy : Sicily

Walking the Highlights of Western Sicily

£1159


4.5 (104 reviews)

VIEW TRIP

Self-guided walking

7 nights,
twin centre

Level: 2
Moderate

Headwater
Navigation App

BOOK NOW & RECEIVE A SELECTION OF WINE

VIEW TRIP

Italy : Sicily

Volcanoes of Sicily Walk

£1499


4.4 (12 reviews)

VIEW TRIP

Self-guided walking

7 nights,
hotel-to-hotel

Level: 2
Moderate

Headwater
Navigation App

BOOK NOW & RECEIVE A SELECTION OF WINE

VIEW TRIP

Italy : Sicily

Secrets of Sicily Cycling

£1339


4.6 (25 reviews)

VIEW TRIP

Self-guided cycling

7 nights,
hotel-to-hotel

Level: 1+
Leisurely plus

1 meals
included

BOOK NOW & RECEIVE A SELECTION OF WINE

VIEW TRIP

Italy : Sicily

Cycling through Baroque Sicily

£1629


4.5 (23 reviews)

VIEW TRIP

Self-guided cycling

8 nights,
hotel-to-hotel

Level: 2
Moderate

3 meals
included

BOOK NOW & RECEIVE A SELECTION OF WINE

VIEW TRIP

Italy : Sicily

Sicily: Vino & Volcanoes

£1449


5.0 (2 reviews)

VIEW TRIP

Cultural tour

7 nights,
hotel-to-hotel

8 meals
included

Headwater
Navigation App

BOOK NOW & RECEIVE A SELECTION OF WINE

VIEW TRIP
Tap here to filter results

Filter and sort

Holiday type
All

  • Self-guided walking
  • Self-guided cycling
  • Ski holidays
  • Canoeing
  • Multi activity
  • Pilgrimage
  • Private guided walking
  • Cultural tour
  • Guided group walking
  • Guided group cycling

Destination
All

  • Italy
  • Spain
  • France
  • Portugal
  • UK
  • Albania
  • Andorra
  • Austria
  • Belgium
  • Bermuda
  • Bosnia
  • Canada
  • Cape Verde
  • China
  • Costa Rica
  • Croatia
  • Cyprus
  • Czechia
  • Denmark
  • Ecuador
  • Egypt
  • Estonia
  • Faroe Islands
  • Finland
  • Germany
  • Greece
  • Holland
  • Iceland
  • India
  • Ireland
  • Japan
  • Malta + Gozo
  • Montenegro
  • Morocco
  • New Zealand
  • Norway
  • Peru
  • Romania
  • Slovakia
  • Slovenia
  • South Africa
  • Sri Lanka
  • Sweden
  • Switzerland
  • Thailand
  • USA
  • Vietnam
  • New Zealand

Departure month
All

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Activity level
All


  • Leisurely

  • Moderate

  • Demanding

  • Challenging

Accommodation type
All


  • Single centre

  • Twin centre  

  • Hotel-to-hotel

Best for
All

  • Singles
  • Couples
  • Families
  • Food lovers
  • Wine lovers
  • Nature lovers
  • Bird watchers
  • Historic sites
  • Vegetarians
  • Swimming opportunities
  • Electric bikes
  • Tandem bikes
  • Headwater Navigation App
  • Dog friendly
  • Positive impact
  • In luxury
  • Coastal routes
  • Island exploring
  • Lakes and rivers
  • High peaks
  • Parador hotels
  • Multi-country trips
  • New holidays
  • Bestsellers

Sorted by


  • Price

  • Duration

  • Level

Update filters

 

Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.

Why choose Headwater for walking or 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.

LEARN MORE ABOUT HEADWATER