Sicily & Aeolian Islands Grand Tour



13 – 25 May 2021 > Click HERE TO BOOK this tour

5 – 17 April 2022 > Click HERE TO BOOK this tour

17 – 29 October 2022 > Click HERE TO BOOK this tour

Discover Sicily and the Aeolian Islands with us on our walking tour. Sicily is a magical island-museum full of unexpected treasures. spectacular scenery and superb food. We also explore the historic and mythological Volcanic Aeolian Islands situated in the Mediterranean Sea north of Sicily and named after the mythological god of the winds, Aeolus.

On our Sicily & Aeolian Islands Grand Tour, you will see many of the world’s most beautiful and evocative monuments, traditions, flavours, and peculiarities. We will walk through the best parts of Sicily and the Aeolian Islands including many of its UNESCO World Heritage Sites. Our passion for guiding in Caspin’s unique style will deepen your knowledge of Sicily and the Aeolian Islands, the Heartbeat of the Mediterranean.

  • Reviews 0 Reviews
  • Vacation Style Holiday Type
    Walking & Hiking
  • Activity Level Moderate
  • Group Size Small Group
All about the Sicily & Aeolian Islands Grand Tour.

Sure Footed Sicily

DURATION: 13 days

PICK UP & DROP OFF: Palermo Airport

Sicily itinerary map with Caspin Journeys
Discover Sicily with Caspin Journeys

“Sicily has had 13 foreign dominations and this is reflected in its culture. Nothing is quite like it! Sicily is a fascinating place, quite unlike any other.”
Andrea Camilleri

We journey at a walking pace through scenery and monuments giving us time to enjoy and absorb each moment to the full. Sicily is a living testimony to the contribution made by different cultures over time. Sicily is also famous for hospitality, gourmet food, panoramas and not least tales, legends and curiosities re-evoked time and time again. Think of Homer’s Odyssey and Francis Ford Coppola’s infamous Godfather!

On this well-tested tour you will travel at a perfect pace. Our small group walking tour of Sicily is immensely popular. It is a large island and you are accompanied throughout by knowledgeable historians and archaeologists.

Sicily is a magical island-museum where you can see many unexpected treasures and walk in spectacular scenery. Picture the 2000-year-old columns of a superbly preserved Doric Greek temple standing at the foot of rugged mountains, bathed in sun and colourfully carpeted with wild flowers. Experience the remote Madonie mountains, encounter seas of wild flowers, visit a hidden cave with Paleolithic and Neolithic paintings, and enjoy picnic feasts among vines and olives.

Piazza Armerina Mosaic detail

We visit the forty mosaic floors in the finest Roman Villa ever to have been discovered. There are mosaics decorating fine Norman Cathedrals. And then walk along medieval cobbled streets where time seems to have stood still and dip your toes in the breathtaking blue and emerald green of the Mediterranean Sea while enjoying spectacular views of the active volcano Mt Etna.

Sicilian people are welcoming, warm and hospitable; the food embraces the aromas of the sun, sea and soil; a wonderful blend of woodland and sea flavours; swordfish, pine nuts, raisins and wild fennel; oranges and lemons simply bursting with sweet juices; ricotta cheese in specialties such as Cannoli; the ingredients are delicious, hearty and great fun at the end of every exciting day.

In Sicily everything is a high point: you are at the heartbeat of the Mediterranean; a mythical island of great enchantment, bathed in sun, blessed by its plants, flowers and fruit, and home to people who are warm and hospitable and greet the stranger as a far-flung friend.

If you would like to speak with us to know more about our Sicily & Aeolian Islands Grand Tour and to get help planning your trip, please write us an email. We would be happy to hear from you and help you planning your next adventure!

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 2 experienced guides 24/7
  • All breakfasts, lunches and dinners as per itinerary
  • Wine, water & coffee with meals
  • All accommodations
  • All gratuities for hotel porters and waiters
  • Minibus transport from start to finish
  • Entrance fees to museums, events and parks as listed on itinerary
  • Local specialist guiding fees
What is not included in this tour?Items that are not included in the cost of tour price.
  • Flights
  • Transfer to the meeting point
  • Travel insurance and other emergencies
  • Visa fees and entry clearing fees
  • Single room accommodations
  • 2 lunches, 1 dinner
  • Minibar
  1. Arrival - Lo Zingaro Nature Reserve - Erice walk 12km

    We meet at 13.00 at Palermo airport; drive to Scopello to walk in the Zingaro Nature Reserve (boots required). Enjoy the rugged, Sicilian coastline and learn how locals used to make a living form tuna fishing and basket weaving. If lucky, we may spot a peregrine falcon. High above the coast, admire the colours of the Mediterranean. In the afternoon enjoy a gelato or cappuccino in a local cafe and stroll around the charming narrow streets of Erice. The town has a sweeping view of the valley below and is famous for almond pastries. The cobbled streets of Erice are charming to explore and its roots date back to the Trojan refugees.

    Meals: Dinner
    Walk: 4hrs / 12km; Elev. +/- 500ft

  2. Egadi Islands Walk walk 11 km

    From Trapani we take a hydrofoil to Levanzo and walk across the hinterland to a hidden cave, the Grotta del Genovese (Cave of Genovese). Through an enlarged rabbit warren we enter the cave to admire a beautiful example of ancient art: the graffiti date back to 11-12 thousand years ago and they represent a treasure of Palaeolithic and Neolithic drawings. 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
    Walk:  3.5hrs / 11km; Elev. +/- 400ft

  3. Segesta - Agrigento walk 10 km

    We visit the Greco-Trojan city of Segesta at the top of Monte Barbaro to see the IV BC theatre which has a stunning view overlooking the countryside and sea, walking down afterwards to the unfinished Doric temple – situated one a truly incredible setting – and then on to a forest
    track on the other side of the river gorge for a delicious picnic lunch with a panoramic view of the temple. Afternoon drive down the south coast past vineyards, orange orchards and olive groves.

    Meals: Breakfast / Lunch / Dinner
    Walk:  3hrs / 10km

  4. Agrigento & Valley of the Temples walk 8 km

    A pleasant morning beach walk takes us to the unusual Scala dei Turchi promontory (2hrs/6.5km). In the afternoon we visit the museum of Agrigento with a local guide. Inside is an excellent collection of artefacts, temple decorations, a giant statue from the temple of Zeus, votive offerings and a model of the largest temple in Magna Graecia. 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., 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:  5hrs / 8km

  5. Piazza Armerina - Roman Villa Casale walk 8 km

    We drive to Piazza Armerina, located in the heart of Sicily known as ‘the bread basket of Rome’. Here we visit the very fine Roman Imperial Villa Casale, another beautiful UNESCO heritage site, with over forty pictorial mosaic floors life of the rich roman citizens. A pleasant walk takes us over a hill, past fresh water fountains and enters the medieval town of Piazza Armerina where we stop for a delicious gelato. We end the day in Siracusa on Ortygia Island.

    FOCUS: The Villa Romana, 300-400 A.D., a great example of luxury Roman living in Sicily. It is located far from the sea in the centre of the island at the foot of Mount Mangone. The exceptional beauty and quality of mosaic floors which decorate the villa illustrate its greatness and underline the importance of the island of Sicily in imperial Roman times.

    Meals: Breakfast / Lunch / Dinner
    Walk:  2.5hrs / 8km; Elev. +/-600ft

  6. Siracusa free morning - guided tour strolling through ruins

    A leisurely morning to explore the historic quarters of Siracusa and experience the lively fish market.

    In the afternoon our local guide explains the historical scenery as we explore the Ear of Dionysius, the Greek theatre, the Roman amphitheatre and the Altar of Hieron. We learn about Siracusa, arch enemy of Athens, once capital of Magna Graecia and the most powerful city of the Greek world.

    The day ends on the island of Ortigia at the 2500 year-old building which today is the Cathedral of Siracusa.

    FOCUS: The Ancient Syracuse including Ortygia, 800 B.C., birth place of Archimedes and founded by Greeks. Ancient Syracuse contains, among other things, the remains of the Temple of Athena still used today as the Cathedral, the single stone carved Greek Theatre and a Roman amphitheatre.

    Meals: Breakfast / Dinner
    Walk:  3hrs strolling

  7. Pantalica gorge walk 9.5 km

    We head out for a vigorous, stunning walk in the rocky gorge of Pantalica in the Iblei mountains. The canyon is like a honeycomb with thousands of 4000 year old burial chambers of various shapes and sizes. The gorge is a place of great natural beauty, a deep limestone ravine carved out
    over millennia by the Anapo and Calcinara rivers along which a variety of flora flourish.

    FOCUS: the Necropolis of Pantalica containing more than 5,000 tombs, mainly dating back from XIII to VII Centuries BC.

    Meals: Breakfast / Lunch
    Walk: 3hrs/9.5km; Elev. +/- 500ft

  8. Taormina - Castelmola free day

    Free day to explore the charming streets of Taormina, Sicily’s most famous resort town and also Castelmola. Visit the Greco-Roman amphitheatre, do a little shopping, sit in a street cafe and watch the world go by. Optional guided walk along ancient mule tracks down into Taormina and then continuing down to Mazzaro’ beach for lunch.

    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 almost everywhere.

    Meals: Breakfast / Lunch / Dinner

  9. Aeolian Islands: Vulcano walk - Panarea walk 9 km

    We drive to Milazzo and catch a hydrofoil to Vulcano for the unforgettable experience of walking up a volcano, going around the rim and looking into the smouldering sulphurous crater (1280ft). Afternoon boat excursion to reach our accommodations in Panarea (transportation by hydrofoil and private boat).

    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 the land of Sicily by 200 m deep waters. The two different kinds of eruption (Vulcanian and Strombolian) have given the science of volcanology a chance to enrich and improve their knowledge.

    Meals: Breakfast / Lunch / Dinner
    Walk: 4hrs/9km

  10. Panarea walk - Stromboli by night walk 8 km

    Scenic circular walk around the island of Panarea and onto the ancient crater wall where a Bronze Age village has been discovered at the south-west end of the island.

    In the afternoon we take a private boat across to the active volcanic island of Stromboli where you can still see the lava flows by night. These islands are inspirational to film makers and more recently Il Postino was filmed here. (walk 3-4hrs; private boat excursion).

    Meals: Breakfast / Lunch / Dinner
    Walk: 3hrs/8km

  11. Cefalù strolling around Cefalù

    We travel by hydrofoil back to mainland Sicily. Today we visit Cefalu’s charming old quarters, the Norman Cathedral with free time in the bustling fishing town. If you are feeling sprightly you can walk with us up to the Rocca promontory with walls and castle ruins offering magnificent views of the harbour, town and emerald blue sea. (hydrofoil; strolling day). *lunch independently.

    FOCUS: the Arab-Norman architecture, 1130-1194, dates from the time of the Norman Kingdom of Sicily. An architectural circuit winds its way through the civil and religious monuments of the city of Palermo and the cathedrals of Monreale and Cefalu. This is a unique historical example of social and cultural syncretism (amalgamation of different religions and cultures) and testimony to the fruitful coexistence of different religions and cultures, Christians, Muslims and Jews.

    Meals: Breakfast / Dinner
    Walk: strolling around Cefalù

  12. Madonie Mountains National Park 13 km

    A walk in the heart of the Madonie mountains, an area seldom visited and of ancient traditions. We stroll through the cobbled streets of Geraci Siculo where time seems to have stood still. Our hiking trail climbs through pine forests to Pizzo Corvo where we emerge and cross mountain pastures through awe-inspiring scenery with occasional views of Mt. Etna, the sleeping giant which looms at a distance of over 50 miles as we approach Petralia Soprana. (4hrs/13km) (Elev. +/-300m)

    Meals: Breakfast / Lunch / Dinner
    Walk: 4hrs/13km; Elev. +/-300m

  13. Departure

    Departure from our hotel at 9.00 to transfer to Palermo Airport.

    We recommend you book flights departing after 14.00; allow about 2.5 hours to reach the airport. If you wish, we can help you to extend your stay or make other independent departure arrangements such as early taxis to the airport.

    Meals: Breakfast

Sicilian Atmosphere

We will create unforgettable memories!

Accommodation Standard

Accommodations are an important point of your overall holiday experience. One of our first thought is to find and choose the best hotel and b&b solutions, ensuring that each night of your itinerary finds you comfortably settled in a space that is welcoming and full of authentic local charm.

When considering a hotel, we look at more than just the rooms and wherever possible, we arrange for stays close to the places you most dream of seeing like historically iconic, coveted high-design or supremely located at the edge of a wilderness.

Take a closer look at some of the properties we have chosen for your next Caspin Journeys holiday!

SicilySome of the dream hotels you will find on this tour
Relais Santa Anastasia
Hotel Villa Sonia
Hotel Baglio della Luna

Click here to send us an email with your enquiry. If you prefer us to call you back, please provide also your telephone number and the best day and time suite you to receive a call from us.

Yes, it’s possible.

Once you have chosen your tour, click on the Book Now button. It will redirect you to our online booking form. Once you have payed a 25% deposit out of the total tour price, you can consider your booking confirmed.

Feel free to decide the best payment method for your needs! We accept credit/debit cards and bank transfer.

Please don’t hesitate to contact us if you have any other requirement.

When it will be time to pay the balance, we will send you an email with the payment request. We will assist you through all the steps and we will be available to answer to all your questions.

Absolutely, no problem!
Request our bank details:

We will be happy to assist you with your booking!

You should fly into and out from Palermo Airport.

Pick up for this tour is at Palermo Airport.

Drop off is at Palermo Airport too.

If you plan on arriving a few days early and will not be flying in on pick up day, contact us and we can work together to arrange a more convenient pick up location for you.

Overall Rating