sicily hiking cultural tour

Sicily’s ancient ruins are some of the best in the Mediterranean

Greek and Roman civilizations left their mark on Sicily, the largest island in the Mediterranean. Our hikes bring us to the Madonie Mountains, the idyllic Aeolian Islands, and Mt. Etna as we celebrate Sicily’s natural beauty and multi-layered culture.

Photo by Brian McGilloway

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Hiking in Sicily route-map

Trip Details at-a-Glance

Cost From: $5195  
Length: 11 days
Arrive: Palermo, Italy
Depart: Catania, Italy
Lodging: 10 nights small inns and hotels
Meals: All meals included except 1 lunch and 4 dinners
Activity: Hiking / Trekking, Cultural Adventures
Trip Level: A mix of moderate walks and hikes, some steep trails, 2-4 hours a day, altitudes up to 10,000 feet, van support (for luggage or if you wish to skip a day's hike)


  • Hike the spectacular coastal trails of Zingaro, the mountain gorge of Pantalica, and on fiery Mt. Etna
  • Neolithic rock tombs, Norman cathedrals, Greek temples
  • Seaside Cefalú, picturesque Taormina, amazing mosaics of Villa Romana del Casale, a World Heritage Site
  • Delight in Sicily’s unique cuisine, fresh from the land and sea

I would recommend this trip to anyone who wants to walk and experience Sicily in an up close and personal way. The three trip leaders made this happen.Paul M.—Olney, MD

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Choosing the Right Trip

We work hard to help you choose the right trip for you, paying attention to your individual interests, abilities, and needs. If you have questions about the level of comfort or any of the activities described in this itinerary, please contact us.


We are proud to have an exceptionally high rate of repeat travelers. For more information, we would be happy to put you in touch with a client who has traveled with us.

Sicily is a sun-drenched world all its own, with a fascinating 3,000-year-old history and flourishing traditional culture. On this captivating island, you’ll hike coastal trails above a turquoise sea, meander across rolling vineyards, and head into Sicily’s wild inland mountains, a pastoral world of tiny farms and villages. Our adventures include a breathtaking hike on Mt. Etna, the rock tombs of the Pantalica Gorge, and the grand mosaics of the Villa Romana del Casale. Along the way, you’ll feast on fragrant cuisine infused with tangy North African flavors—wonderful frutti di mare, arancini, caponata—this is Sicily!

Itinerary at a Glance

For a more complete description, Download Full Detailed Itinerary

Days 1-4
Palermo / Segesta / Zingaro Nature Reserve / Monreale / Cefalú

Our visit to Segesta’s stunning Greek temple is followed by a cove-to-cove hike above isolated beaches at Zingaro. After a hike through vineyards and orchards, we head to Monreale’s 12th century cathedral to see its dazzling Greek and Byzantine mosaics. From Cefalú, our hike is in the Madonie Mountains, where Sicily’s deeply rustic culture still thrives.

Days 5-8
Piazza Armerina / Pantalica Gorge / Siracusa

View the extraordinary mosaics of the Villa Romana del Casale, then enjoy a cooking class at a local winery. A hike in the Pantalica Gorge reveals thousands of rock-hewn Neolithic tombs adorning the canyon walls, and in Siracusa, you’ll explore breathtaking Greek and Roman ruins on foot.

Days 9-11
Mt. Etna / Taormina / Catania

Our hike on Mt. Etna brings you across extraordinary lava landscapes, and in Taormina, perched high above two sweeping bays, we explore the town’s palazzi-lined streets and 3rd century BC Greek amphitheater, still in use for concerts. Depart on Day 11 via Catania.

For a more complete description, Download Full Detailed Itinerary

What the Trip is Like

This trip is Level 3, or Moderate, according to our trip grading system, and is designed for those who have at least some hiking experience. It features day walks and hikes of 3-8 miles. While the mountains of this beautiful island are not high, the trails can be steep and a bit rugged in places. Please also note that the hiking can feel more demanding at times because the weather can occasionally be hot, even in the lovely spring and early fall periods when we make our journeys. We will carry just a daypack with water bottle, sunscreen, camera, and anything else you want with you while on the trail. Luggage is transported for us by van, so it is always possible to ride in the van if you wish to opt out of a day’s hiking.

After breakfast in our hotel, we generally set off by 9 am. Each day is a bit different. Some days encompass 3-5 hours of country walking; others involve a half day or more exploring, for example, one of the ancient towns on foot. On many days, we have a scenic drive of an hour or two to a starting point for our walk, and get picked up at the end of the walk and driven to our night’s lodging. Our van will meet us for lunch on several days, bringing a picnic of local cheeses, breads, cold meats, assorted salads, fresh vegetables, fruits of the season, and mineral water. Those not up to the afternoon’s walk can often continue with the van back to our hotel.

For maximum enjoyment of the trip (and the wonderful scenery, food, wine, art and history that are a part of it), we recommend you make a special effort to be in good physical condition. Daily brisk walking and/or regular hiking (or using a stair-climbing machine at your gym) are excellent preparatory exercises.

The meals included in the trip itinerary will be taken at the hotels where we are staying or at restaurants in the towns, with the occasional picnic lunch. For lunches and dinners “on your own,” the Trip Leader will be happy to advise you or accompany you to local restaurants and trattorias. Please note that in Europe, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 7:30 pm.

We spend our nights in small, picturesque inns, full of Italian charm and ambiance. All hotels are chosen for their local history and central location. Since they are often in historic buildings the rooms may not conform to uniform international standards. Our leaders try to assign rooms in a fair way so that all participants experience an equal advantage throughout the trip as a whole. Single rooms can be requested, but are not always available, due to the limited space in some of our hotels. If you require a single room, please make the request as early as possible. European single rooms are often smaller than US singles.

Explanation of Trip Levels


Departures & Leaders

Apr 16-26, 2016   Sebastiano Leone
May 7-17, 2016

Sep 10-20, 2016   Francesco Selvaggio
Oct 8-18, 2016

Trip Cost

Prices are for 2016
$5195 (11-15 members)
$5695 (6-10 members)
Single supplement: $830
Forced single supplement: $630
more on pricing

Trip Payment Schedule

At time of reservation: $600
90 days prior to departure: Balance

Cancellation and Transfer Fee Schedule

Up to 91 days prior to departure: No charge!
61-90 days prior to departure: 25% of trip cost
46-60 days prior to departure: 50% of trip cost
45 days or less: 100% of trip cost

Trip Cost Includes:

  • Expert leadership of a Wilderness Travel Trip Leader and local guides
  • Accommodations in hotels and small comfortable inns
  • All meals included except 1 lunch and 4 dinners
  • A glass of wine or beer with dinner
  • Ground transportation throughout the trip

Trip Cost Does Not Include:

International airfare, independent hotel/airport transfers, any meals not specified after each itinerary day in the Full Trip Brochure, airport departure taxes, optional tipping or gratuities to leaders or staff, additional hotel nights that may be necessary due to airline schedule changes or other factors; pre-trip expense of medical immunizations (if any), travel insurance or passports; and other expenses of a personal nature (alcoholic beverages, laundry, etc.).

Arrival & Departure Information

You are responsible for your own transportation to the arrival and from the departure cities listed below. For more detailed information, including transfers, please download the Detailed Itinerary.

Please do not purchase your tickets until you are confirmed on the trip. Once your tickets have been purchased, please send us a copy of your airline schedule.

2016 Departures

Meeting Place:
Palermo, Italy
Date: Day 1

Suggested Arrival Airport:
Palermo, Italy (airport code PMO)
Suggested arrival time:  11:30 am for those arriving Day 1, or anytime one day prior
Catania, Italy
Date: Day 10

Suggested Airport for Departure:
Catania, Italy (airport code CTA)
Suggested departure time: after 10:30 am

Hotel Elimo

Hotel Elimo

Days 1 to 2 (2 nights), Erice, Italy

Located in the historic center of the picturesque mountain town of Erice, the small family-run Hotel Elimo is a perfectly restored, quiet hotel with ...
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La Plumeria Hotel

La Plumeria Hotel

Days 3 to 4 (2 nights), Cefalu, Italy

This 10-room boutique hotel right in the heart of Cefalu’s Old Town is a real gem, just yards from the main square and cathedral. The rooms ...
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Vecchia Masseria

Vecchia Masseria

Days 5 to 6 (2 nights), Caltagirone, Italy

Set at the end of a narrow, one-lane road, the Vecchia Masseria, a working farm, is a great place to end the day after our tour of Villa Romana del ...
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Hotels in Siracusa
Des Etrangers Hotel and Spa

Grand Hotel Ortigia

Grand Hotel Ortigia

Days 7 to 8 (2 nights), Siracusa, Italy

With a convenient location on the waterfront, the Grand Ortigia is a renovated turn-of-the-century hotel with comfortable rooms, a good breakfast, ...
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Ashbee Hotel

Ashbee Hotel

Days 9 to 10 (2 nights), Taormina, Italy

The 25-room Ashbee is a renovated private villa built in 1907 by Charles Robert Ashbee, a renowned Arts & Crafts architect. It has a sublime ...
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Note: Listed above are our signature accommodations for this trip. Although it is highly unlikely, we may make substitutions when necessary.

Our Trip Leaders

Here are the Trip Leaders scheduled for this journey (please note that leader assignments are subject to change).

Lisa Halderman

Lisa Halderman experienced Italy in 1973 as a high school exchange student. She earned her degree in Italian Literature, completing her final year at the University of Padua. Her studies have immersed her in the world of Italian art, architecture, politics, and history. An avid gardener, Lisa also ...
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Annie Hawkins

Annie Hawkins, born and raised in a small village in Burgundy, is a passionate world traveler and one of our most enchanting Trip Leaders. After studying art history in Provence, Annie moved to California, where she led adventure tours in the American Southwest and realized that leading adventure ...
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Sebastiano Leone

Departure Dates: April 16-26, 2016, May 7-17, 2016, October 8-18, 2016

Sebastiano Leone knows that traveling through Italy is always better when you’re being led by your senses. From guiding hiking and cultural trips that offer incredible views and insights to Italy’s colorful history, not to mention knowing the local hotspots to sip and savor authentic ...
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Tania Masi

Departure Dates: May 7-17, 2016

Born in Florence, Italy, of an American mother and proud Florentine father, Tania Masi was raised with an appreciation for both American and European cultures. With nine languages and a Master of Geography under her belt—not to mention a career as a journalist and documentary film director ...
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Sergio Mastroberardino

Sergio Mastroberardino was born in the town of Avellino in southern Italy. He is a Certified Alpine Ski Instructor and during the winter season works full time with various ski schools and as a professional ski guide. Sergio has lived and taught skiing in Aspen, Colorado, Val D'Isere, France, and ...
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Francesco Selvaggio

Departure Dates: May 7-17, 2016, September 10-20, 2016, October 8-18, 2016

Francesco Selvaggio, born and raised in Palermo, has a degree in architecture with a concentration on historic restoration and a thesis dedicated to the Sicilian landscape. Francesco loves the life of a Trip Leader because it allows him to pursue passions such as hiking in the Sicilian countryside ...
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Milena Vela

A lover of languages, cultures, and cuisine, Milena Vela is a charming guide who has led trips for us for several years. Originally from the lovely and historic city of Palermo, Italy, Milena has lived and worked in Ireland, Holland, Germany, and England, holds a degree in Foreign Languages and ...
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Client Comments

I would recommend this trip to anyone who wants to walk and experience Sicily in an up close and personal way. The three trip leaders made this happen. Paul M., Olney, MD Probably the best trip I've been on! Sicily was a wonderful surprise. Don M., Atlanta, GA This was an incredible introduction to Sicily. We covered so much of the island, the hikes were all so different, it was a perfect blend of hiking and cultural activities. Margaret K., San Francisco, CA The absolute key to the success of the trip was the leaders, Sebastiano, Lisa, and Tania. They were just superb in every way. We were briefed on the next day's itinerary every evening during the excellent dinners and they were thoroughly professional, knowledgable, and accommodating. Tom G., Los Altos, CA This trip provided a wonderful sampler of Sicily and Sicilian life, past and present. Throughout our trip, the food was exceptional—the best in all of Italy! Johanna S., Sunnyvale, CA A wonderful way to experience Sicily—everything from ancient Greek and Roman sites, medieval churches, and natural phenomena such as Mt. Etna to tasty fresh fish and pasta dishes accompanied by excellent Sicilian wines. Jane S., Albuquerque, NM This is a really fun trip with lots of good food and wine as well as some very nice hiking. Pam M., La Jolla, CA We had a wonderful time. Sicily was fantastic and our enjoyment was enhanced by our three guides. Walter and Anneliese B., Toronto, Ontario Simply put, this was the best trip ever. The deliberate balance of exercise, education, and culinary extravaganzas made each day a feast for the eyes, minds, and bodies. Sandy C., Haverford, PA Ones world expands through travel in many ways, but I think the best medium of that expansion is new friends. Group travel opens that door so that luck can take a hand. Like your trip leaders, the group of clients you attract is exceptional in our experience. We have made some of our best friends while traveling on WT trips. and we continue to travel with them often. Thank-you is in order. Jon R., Hillsborough, CA Everything was well orchestrated, controlled, and managed, the hotels were very good to excellent, and the meals were extremely good. David C., New York, NY Sicily is quite an amazing destination, and we were very happy to experience it through this fine itinerary with these excellent guides. Pam W., Minneapolis, MN
We really felt we saw Sicily and learned a lot about its very rich history. The local guides were excellent, the restaurants were wonderful, and Sebastiano and Francesco obviously cared deeply that we had a fun and memorable trip. Edie L., Dallas, TX I loved the trip, and the balance of city/cultural activities with outdoor/hiking activities was exactly what I expected. Eleanor S., Kingstone, ON Fantastic trip. Good itinerary, wonderful guides, generous with extras such as espressos at every stop. Joselyn B., Caspar, CA I had high hopes for Sicily, though unsure how it would compare to previous Italian trips. It exceeded all expectations by far. One of my most favorite trips. Larry E., Chicago, IL This was a wonderful trip. The places visited were terrific, and the leaders, in particular, made everything worthwhile by their knowledge of the place, their flexibility, and their great sense of humor. Bettina R., Santa Clara, CA This was a fantastic trip for both of us. We loved the blend of experiences that could only be possible on a WT trip, such as sit-down meals, picnics, a walk followed by a superb lunch at a winery, tour and dinner with a baron in Siracuse, wading in the sea, touring ancient sites. Each trip we have been on with Wilderness Travel has exceeded our expectations. This trip stands out even more so. Bob and Shirley B., Ennis, MT Well designed and well run. I especially loved the hikes, and the enthusiasm of the guides was very contagious. John R., Baltimore, MD It was magical—the beauty of Sicily and hiking through the countryside. Barbara Q., Oakdale, NY We had a wonderful time. I felt I had been able to see and experience the ‘real’ Sicily. Diane C., Manchester, MO We enjoyed every minute! Heidi M., Brevard, NC Best trip ever! I loved the small group size with two trip leaders—it allowed for great flexibility. Gail B., Larchmont, NY A wonderful trip with interesting, capable, and kind leaders. We had a great time! Susan W., Portland, OR I must say this was the best vacation that I have ever experienced. Tray B., Chadds Ford, PA Terrific throughout. Our guides were the absolute best. Bravissimi! Edy and Michael D., Portland, OR

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