13 DAYS • 12 NIGHTS
GROUP SIZE: 8 – 12
activity level: MODERATE
FROM € 6,300
DATES & AVAILABILITY
5 – 17 October 2026
SOLD OUT
6 – 18 April 2027
SOLD OUT – JOIN WAITLIST
9 – 21 APRIL 2027
4 – 16 October 2027
SOLD OUT
18 – 30 OCTOBER 2027
FOR PRIVATE GROUPS
OR OTHER INFO
This unique walking experience is a journey through time, leading you from prehistoric cave dwellings into the classical world of the Greeks and Romans, and emerging through the vibrant food and folklore of modern Sicily.
We explore the remote Madonie Mountains and the volcanic Aeolian Islands—named after the mythological god of the winds—where the island’s lively heartbeat is felt most strongly.
Sicily is a magical island-museum of unexpected treasures, where 2,000-year-old Doric columns stand against rugged mountains carpeted in wildflowers. From the sparkling emerald waters of the Mediterranean to the smoking peak of Mt. Etna, this journey invites you to walk at a perfect pace, absorbing the hospitality and “sun-drenched” flavors of Italy’s largest island.
Sicily means spectacular scenery, rich culture, warm hospitality and delicious regional cuisine shared with friends old and new. Each day on our Sicily Walking Tour brings a deeper sense of the island’s spirit, inviting you to connect with its people, places and stories at a pace that allows you to savour every moment.
PICK UP: 11.00 at Palermo airport
DROP OFF: 9.00 transfer to Palermo airport for flights departing after 14.00
We highly recommend staying 1-2 nights in the vibrant city of Palermo before the tour starts, to marvel at the abundance of Arab-Norman palaces, architecture and churches.
We meet at 11.00 at Palermo airport and travel west to enjoy lunch at a farm.
From here we walk along a forest track with a panoramic views of a IV century BC Greek temple. We explore the hilltop site of Segesta, its well-preserved Temple and a monolithic Theatre with a stunning view of the surrounding countryside.
We then continue to the mountain top town of Erice, one of Sicily’s oldest settlements, where you can wander cobbled streets and taste famous almond pastries before we meet for our welcome dinner.
Meals: Lunch, Dinner
Hike: 2 hrs / 7 km
Overnight: Erice
From Trapani we take a hydrofoil to the island of Levanzo. We walk across the hinterland to reach the hidden cave, Grotta del Genovese, containing a treasure of Palaeolithic and Neolithic drawings dating back over 11,000 years.
We continue around the island with views of Favignana and Marettimo, the other two islands of this archipelago, set in crystal clear blue waters.
We return mid-afternoon to explore the charming town of Erice.
Meals: Breakfast, Lunch, Dinner
Hike: 3.5hrs / 11km; Elev. +/- 400m
Overnight: Erice
A spectacular morning drive with an incredible panorama leads to the Zingaro Nature Reserve. Here we take a walk in its untamed and scented Mediterranean scrub that stretches along the coast over the emerald green and cobalt blue waters of the Mediterranean Sea. This is where the enormous Bluefin Tuna come to lay their eggs.
Enjoy the rugged, Sicilian coastline and learn how locals used to make a living from tuna fishing and basket weaving. If lucky, we may spot a peregrine falcon.
After lunch with a view we continue south to our next destination, the UNESCO heritage Valley of the Temples in Agrigento.
Meals: Breakfast, Lunch, Dinner
Walk: 4 hrs / 11 km
Overnight: Agrigento
Today we delve deep into the heart of Greek civilization. We visit the museum of Agrigento to see an excellent collection of artifacts, including votive offerings and a giant statue from the temple of Zeus.
We then walk through the Valley of the Temples, UNESCO world heritage site, discussing Greek civilisation and why Pindar described Akragas as ‘most beautiful of mortal cities’.
FOCUS: The ancient city of Agrigento, 600 B.C., was one of the greatest Mediterranean centres of antiquity. The remains of the Doric Temples which dominate the city and known as the Valley of the Temples are well preserved and are Testimony to one of the most prominent periods of Greek art and culture. They testify to the magnificence and supremacy of the ancient Greek culture.
Meals: Breakfast, Lunch, Dinner
Walk: 2 hrs + 3 hrs / 8km
Overnight: Agrigento
We drive to Piazza Armerina, located in the heart of Sicily known as ‘the bread basket of Rome’. Here we visit the fine Roman Imperial Villa Casale, another beautiful UNESCO heritage site, with pictorial mosaic floors illustrating the lifestyle of rich roman citizens. We end the day in Siracusa on Ortigia Island with an orientation walk of the town.
FOCUS: The Villa Romana, 300-400 A.D., a great example of luxury Roman living in the centre of the island of Sicily. The exceptional beauty and quality of the mosaic floors underline the importance of Sicily in imperial Roman times.
Meals: Breakfast, Lunch, Dinner
Walk: 2 hrs Walking in the archaeological ruins and 1 hr in the island town of Ortigia
Overnight: Siracusa
We meet after breakfast to go for a 2 hour guided walking tour in Siracusa’s archaeological park to explore the monumental Greco-Roman remains including a quarry, open-air theatre, sacrificial altar and an amphitheatre. We learn how Siracusa, as the arch-enemy of ancient Athens for a while became the most powerful city of the ancient Greek world.
The rest of the day is for free exploration. Don’t forget to stroll around the lively market with fishmongers, colourful fruit and vegetables displays, an array of spices and local cheese. This is a great place to pick up something tasty for your lunch!
FOCUS: Greek Siracusa in 800 B.C. – the birthplace of Archimedes, the remains of Greek temples under the town hall and inside the Cathedral which has also been a mosque! and most amazing of all, a Greek theatre carved out of a single stone hillside.
Meals: Breakfast
Walk: 2hrs exploring the archaeological ruins
Overnight: Siracusa
We head out for a vigorous, stunning walk in the Unesco World Heritage site of Pantalica, a marvel of archaeology and nature immersed in the breath-taking and silent gorges of the Iblei Mountains.
This mysterious place is a deep limestone ravine that has been carved out over time by the Anapo river. At the top is a unique archeological testimony from the Prehistoric to the Byzantines ages; there are thousands of rock-cut tombs of various shapes and sizes on the steep cliffs of the canyon making it look like a giant honeycomb! As we reach the bottom, we find lush vegetation and a plethora of flourishing flora as we walk the old tunnels and trails of a disused railway.
We now continue to our hotel in Castelmola, just above Taormina.
Meals: Breakfast, Lunch, Dinner
Hike: 3hrs/9.5km; Elev. +/- 200m
Overnight: Castelmola
Free day to explore the charming streets of Taormina, Sicily’s most famous resort town. Visit the Greco-Roman amphitheatre, do a little shopping, sit in a street café and watch the world go by. Optional guided walk along ancient mule tracks down into Taormina.
FOCUS: Mount Etna Views– the most active and highest volcano in Europe is of geological, scientific and cultural value; with intense and persistent volcanic activity. Mount Etna dominates the skyline in Taormina and is visible from everywhere.
Meals: Breakfast, Dinner
Walk: 1.5 hrs / 5 km
Overnight: Castelmola
We drive to Milazzo and catch a hydrofoil to Vulcano for the unforgettable experience of walking up and down a volcano*, going around the rim and looking into the sulfurous crater.
Afternoon private boat excursion to reach our accommodation in Panarea.
FOCUS: the Aeolian Islands, a 7-island archipelago (Panarea, Stromboli, Vulcano, Alicudi, Filicudi, Lipari and Salina) located north of the coast of Sicily have volcanic origins and separated from Sicily by deep waters.
Meals: Breakfast / Lunch / Dinner
Hike: 4 hrs / 9km / ascent +500 m
Overnight: Panarea
*Vulcano crater walk is occasionally inaccessible.
Scenic circular walk around the island of Panarea (optional hike to the very top), and onto the ancient crater wall where a Bronze Age village has been discovered. These islands are inspirational to film makers. Take an afternoon stroll around the village and an aperitif by the port and enjoy the slow pace of this special place.
Meals: Breakfast, Lunch, Dinner
Walk: 3 hrs. / 10 km, +/- 450m
Overnight: Panarea
Today we return to the mainland to immerse ourselves in the authentic local life of Castelbuono. We meet with a local producer to discover the unique flavours of the Madonie mountains, a region celebrated for its commitment to the “Slow Food” movement and traditional methods.
This afternoon we visit Cefalu’s charming old quarters, the Norman Cathedral and have some free time to explore the bustling fishing town. The Arab-Norman architecture of Cefalu’ (1130-1194) is a unique historical example of the fruitful coexistence of different religions and cultures, Christians, Muslims and Jews.
Meals: Breakfast, Lunch, Dinner
Walk: strolling around Cefalù
Overnight: Castelbuono
Our final walk takes us into the heart of the seldom explored Madonie Mountains, a UNESCO Global Geopark with an incredible biodiversity of over o over 1,600 plant species. We hike through lush forests to discover the Madonie’s most well-kept secret: some of the oldest and largest Holly Oak trees in Europe. These ancient, monumental giants—some nearly a millennium old— create a fairytale atmosphere that is utterly unexpected in Sicily.
In the evening we head back to explore Castlebuono and enjoy our farewell dinner, in a very special place.
Meals: Breakfast, Lunch, Dinner
Walk: 4 hrs / 13km; Elev. +/-300m
Overnight: Castelbuono
13 DAYS • 12 NIGHTS
GROUP SIZE: 8 – 12
activity level: MODERATE
FROM € 6,300
DATES & AVAILABILITY
05 – 17 October 2026
SOLD OUT
6 – 18 April 2027
SOLD OUT – JOIN WAITLIST
9 – 21 APRIL 2027
04 – 16 October 2027
SOLD OUT
18 – 30 OCTOBER 2027
FOR PRIVATE GROUPS OR OTHER INFO
We believe we are likely the only tour that covers the sheer breadth and depth of Sicily in a single journey. While many itineraries focus on one corner, we traverse the entire island from North to West, South, and East. You will explore the prehistoric Grotta del Genovese on the Egadi Islands in the west and ascend the volcanic craters of the Aeolian Islands in the north-east. From the remote Madonie Mountains to the ancient Greek soul of Siracusa , this “island-museum” experience offers an unparalleled look at 5,000 years of history alongside modern Sicilian hospitality.
We meet at 11.00 at Palermo airport on Day 1.
*It is possible we can arrange a pick p at 9.00 at the NH Hotel in Palermo city centre. Please double check with us before the tour starts.
For international travellers arriving from the US, Canada, or Australia, the most efficient route is to fly into Palermo International Airport (PMO).
We highly recommend staying 1–2 nights in the incredible city of Palermo before the tour starts to settle in and beat jet lag.
This tour is rated as Moderate offers a mix of archaeological strolls and invigorating hikes.
Sicilian cuisine is a true “tour of the senses” featuring sun-drenched flavours that range from fresh seafood and the famous Bluefin Tuna of the Mediterranean to the iconic sweet ricotta cannoli and almond pastries of Erice. Throughout the journey, you will savour authentic meals at local farms and tiny villages, meet producers, and be hosted by private chefs.
We stay in locally-owned, high-quality hotels chosen for their character and location. From a mountain-top town above Taormina to a unique overnight stay on the island of Panarea , our accommodations balance authentic culture with superior service and comfort.
We schedule our tours for early spring and late autumn to ensure the most comfortable hiking conditions.
Sicily’s terrain is diverse, so we recommend a versatile layering system.
How do I book this tour with Caspin Journeys?
To book, click on the BOOK NOW button next to your preferred departure date on our website or contact us via inquiries@caspin.com
A deposit reserves your spot, and the balance is due ahead of the tour.
Is travel insurance required?
Yes. All participants must have comprehensive travel insurance that covers medical emergencies, trip cancellation, evacuation, and loss/damage of personal items.
Can I join as a solo traveller?
Yes — solo travellers are welcome. In the moment of booking, choose the single room option.
What about tips?
This question comes up a lot. Tips and gratuities for most services during the trip such as restaurant staff, porters etc. are included and handled by Caspin Journeys.
As for your tour leaders we at Caspin leave this gesture to your discretion.
SICILY | OCTOBER 2027
Our Autumn departure is full, so we’re considering another Sicily tour.
Register your interest here — no commitment, no deposit. If enough walkers come forward, we’ll confirm this 18 – 30 October 2027 departure and you’ll be first to hear it.
We’ll be in touch as soon as possible. Your information stays with us — no third-party marketing, ever.
If you have already booked to travel with us,
the link below will redirect you to your WeTravel account — our secure booking platform — where you can manage your booking, check your payment status, and much more.
DON’T HAVE A BOOKING YET?
