Active Holidays in Sicily

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.

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Secrets of Sicily Walking
Italy: Sicily

Secrets of Sicily Walking

This triple centre holiday explores the unspoilt north western tip of Sicily and the nearby Egadi islands. It's a relatively undiscovered region where highlights include pristine sandy beaches, coral-lined grottoes, ancient hill villages and marvellously preserved nature reserves.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07MR
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2450per person, tour only

  • 96 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Volcanoes of Sicily Walk
Italy: Sicily

Volcanoes of Sicily Walk

Undoubtedly one of the most spectacular, varied and unique walks in our portfolio, taking in the beautiful Aeolian Islands as well as the immense and impressive Mount Etna - the largest active volcano in Europe!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07AI
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2555per person, tour only

  • 5 Reviews
  • All accommodation
  • All continental breakfasts
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
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$2510per person, tour only

  • 21 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$3410per person, tour only

  • 19 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)
Sicily: Vino & Volcanoes
Italy: Sicily

Sicily: Vino & Volcanoes

Uncover the hidden gems and must-see sights of Eastern Sicily. From local wine tastings to volcanic walks up Mount Etna, this independent tour highlights the very best of the islands natural beauty.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeT07SI
  • Holiday typeIndependent tour
  • Duration7 nights, hotel-to-hotel
  • Excellent for
  • From US$3800per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)

Frequently asked questions

Can you walk around Sicily?

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.

What time of year is best for walking in Sicily?

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.

How many days in Sicily is enough?

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.

What is the most scenic route in Sicily?

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!

What to expect from your walking holiday in Sicily?

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:

  • Hotel accommodation included and pre-booked by us
  • Routes, maps, and detailed notes
  • GPS route directions
  • Dedicated luggage moving, so you won't have to carry around your heavy bags
  • Optional flights and airport transfers

What should I pack for a walking holiday in Sicily?

You'll need to bring along your typical walking clothes, boots, and sunglasses, but we also recommend you pack:

  • Sun hat/cap
  • High SPF sun protection
  • Light jacket
  • Water bottles and/or hydration systems
  • Small backpack for carrying essentials
  • Basic first aid kit, including any medication you might need
  • Plenty of snacks
  • Wallet with foreign currency cash
  • Compass, notepad, and pencil

What should I wear on a walking holiday in Sicily?

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.

Where should I stay in Sicily for a walking holiday?

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.

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?

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

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.

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