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.
Self-guided walking
7 nights,
twin centre
Level: 2
Moderate
Headwater
Navigation App
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Self-guided cycling
7 nights,
hotel-to-hotel
Level: 1+
Leisurely plus
Headwater
Navigation App
Self-guided cycling
8 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
Tap here to filter results
Filter and sort
Holiday type
All
Destination
All
Departure month
All
Activity level
All
Accommodation type
All
Best for
All
Sorted by
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.
Of course! Sicily is an excellent location for walking enthusiasts, offering trails for beginners and experienced hikers. The beautiful region has something for everyone, which makes it a popular destination for walking holidays.
We recommend you book your Sicily walking tour for mid-to-late spring (April to May) or early autumn (September to October). The temperatures are ideal for walking, and you'll avoid the busy crowds who flock to the region in the heart of the summer months.
Our Sicily walking holidays offer seven-night stays, allowing you to explore the region at your own pace. You can spend your days sight-seeing, admiring the landscapes, or taking part in local activities. A week-long holiday will ensure you get to fully discover this Mediterranean paradise.
As the region is known for its diverse landscape, each Sicilian walking route provides picture-perfect scenery. With miles of beautiful coastline and ancient ruins to admire, you'll be spoilt for choice whichever route you take. Our Secrets of Sicily walking route explores the unspoilt north western part of the island, as well as the nearby Egadi islands. Head down to the pristine beaches, stroll through the ancient hill villages, and marvel at the preserved nature reserves. Perhaps you'd like to take on our Volcanoes of Sicily walk? It's one of our most marvellous and unique walks - you'll get to wander the beautiful Aeolian islands while volcano spotting along the way!
If you've always wanted to explore Italy on foot, our walking holidays in Sicily could be just right for you. Ideal for those who love the great outdoors and enjoy staying active, our walking tours will ensure you are up and about for most of the day.
Each of our self-guided walking tours comes with a full itinerary, allowing you to explore the region at your own pace. You'll have the opportunity to get involved with the local cuisine, history, and culture, which will make for the perfect adventure.
When you book with Headwater, you can expect an excellent level of service. We want to make your holiday as smooth as possible, with benefits including:
You'll need to bring along your typical walking clothes, boots, and sunglasses, but we also recommend you pack:
Walking in Sicily will typically require you to dress for the warm and humid conditions. You must wear comfortable, weather-appropriate, and breathable clothing, as well as sturdy walking boots. Ensure you stay protected from the sun and wear a hat, sunglasses, and plenty of SPF.
You'll pass through towns on your route which are home to hotels. However, when you book a holiday with us, we'll arrange all your accommodation to guarantee hassle-free travel.
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.
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.
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.
There are four ways to start your Sicily cycling tour booking with us:
