Fascinating ruins of early civilizations and beautiful coastal paths above the turquoise waters of the Mediterranean are ours to discover on this exploration of ancient Sicily.
Italy Trip Overview
The largest island in the Mediterranean Sea, Sicily boasts a diverse and historic culture dating back to ancient times. Known as “Trinacria” to the early Romans due to its triangular shape, Sicily has become a haven for refreshing cuisine, historical preservation, and breathtaking archeological sites. Our adventure unfolds as we leave the bustle of Palermo and head to the countryside where we spend our days walking the historic hilltops of Erice, the Iato Valley, Castelbuono, Caltabellotta, and Cefalù. Our journey is accented with tastings from the surrounding vineyards, insight into Sicilian gastromony, and the continued ornament of the countryside by the Normans’ magnificent architecture.
Itinerary at a Glance
Day 1: Meet in Palermo and drive towards the medieval hilltop citadel of Erice. Along the way, visit the ancient Greek city of Segesta.
Day 2: Walk along wild coastline in the Monte Cofano Nature Reserve and perhaps take a dip in the Tyrrhenian Sea. Transfer to Menfi.
Day 3: Enjoy a walk through the hilltop village of Caltabellota with sweeping views of the sea and mountains. Visit Selinunte, the largest archeological park in Europe. Learn the secrets of Sicilian cuisine with a cooking class.
Days 4-5: Hike in the Madonie Mountains through villages and farms, before continuing to Castelbuono for a relaxing afternoon. Taste wines from the surrounding vineyards, and celebrate with fine cuisine.
Day 8: Say arrivederci in Taormina, Italy.
Sicily is meant to be savored. Our eight-day walking journey of this ancient island allows sufficient time, and moves at the proper relaxed pace, to experience all that is Sicily - scenic Mediterranean views, fresh gourmet picnics, exceptional dinners, and fascinating ruins. If the Italians don't settle for anything but the finest, why should we?
THE BOUNDLESS JOURNEYS' ADVANTAGE
- A passion for travel. Simply put, we love to travel, and that is woven into every one of our journeys.
- Unique, award-winning itineraries. Our flexible, hand-crafted journeys have received accolades from the world’s most revered travel publications.
- Insider connections. There is simply no substitute for traveling with a knowledgeable insider.
- Small groups. We tread softly, and our average group size is just 6-8 guests.
- Flexibility to suit your travel style. We offer both small-group departures and Private Collection trips.
- Customer service that goes the extra mile. There is no request that is too big – or too small.
- Sustainability. We are committed to traveling responsibly.
Our tours often fill months in advance, and our maximum group size is smaller than most tour operators. It's very quick and easy to reserve a trip. Give us a call at 800-941-8010 or complete the online Reserve a Trip form. We will confirm your reservation with a $500 per person deposit, payable by check or credit card.
Trip Rating (1 Easiest - 5 Most Strenuous)
Traveling to and From
Most Convenient Airport(s):
Palermo, Sicily, Italy (airport code PMO) for the tour meeting point; and Catania, Sicily, Italy (airport code CTA) for the tour departure point. You should plan your flight itinerary to fly into Palermo (PMO), and out of Catania (CTA).
Meeting Time and Place:
Your guide(s) will meet you on Day 1 of your tour after breakfast at 9:00 a.m. in the lobby of the Centrale Palace Hotel in Palermo. Please be checked of your hotel and ready for a day of walking.
Departure Time and Place:
Your guide(s) will provide transportation to the Catania airport (airport code CTA) by 9:00 a.m. on the final day of the tour. Please schedule your flights accordingly, and do not plan your departure time prior to 11:00 a.m. unless you plan on making your own arrangements to the airport. If you have an earlier flight we will be happy to assist you with arrangements at your own expense.
WHAT TO EXPECT
Boundless Journeys’ trips are designed for energetic and flexible individuals who like to be active and have a spirit of adventure and a positive attitude. Ancient Sicily Hiking is rated 2+, easy to moderate, on a scale of 1-5 (with 5 being the most strenuous). It features walks of varying length and difficulty, that average 4-6 hours per day. Our van will usually meet us midday, and our luggage is transported for us, so it is usually possible to ride in the vehicle if you want to opt out of a day’s walking. Please refer to the detailed itinerary for descriptions of the activities on each day of the trip.
Preparing for this Trip
The more well-prepared you are for the activities on this trip, the more you will enjoy yourself! Please engage in moderate aerobic activities (walking, jogging, or cycling) for at least 30-45 minutes several times a week for 4-6 weeks before the trip. If you live in a flat area, try to incorporate some stairs into your workout, or use a treadmill with varying incline capability. Consult your doctor before undertaking any new fitness programs.
Overview: Fine accommodations in ideal locations with beautiful views.
Night 1: Hotel Elimo
In the magnificent setting of the perfectly preserved ancient village of Erice, the Hotel Elimo is a converted estate from the 18th century, and offers the perfect location from which to explore this charming village.
Nights 2 & 3: La Foresteria
La Foresteria boasts views across rolling vineyards to the sea, stylish rooms, a swimming pool, fragrant herb gardens, and a professional kitchen in which guests may observe the preparation of fresh, local cuisine.
Nights 4 & 5: Relais Santa Anastasia
A former abbey, this charming hotel stands on a hill overlooking a valley of vineyards a short distance from the medieval village of Castelbuono.
Nights 6 & 7: Hotel Imperiale
Located in the heart of Taormina's historic center, the 5-star Hotel Imperiale was built at the beginning of the 20th century and reopened in 2009. Each room enjoys a wonderful view of the surrounding panorama, from the roofs of Taormina to the Greek Theater and the beautiful Bay of Naxos.
A Boundless Moment in Sicily...
In the kitchen at La Foresteria, the chef sends soft plumes of flour into the air as he kneads and rolls, creating delicate, even shapes with his hands. Before him is a still-life painting of Sicilian bounty: ruby tomatoes and dark, shiny eggplants; ceramic bowls of green olives and hard-boiled eggs, bouquets of parsley and basil, and bottles of the estate’s own Fiano wine, grown and harvested in the surrounding countryside.
ITALY DETAILED ITINERARY
Iato Valley; transfer to Erice
Walk – easy to moderate, 3.5 hours, along country roads and trails; approximately 6 miles. Drive time approximately 1.5 hours.
En route to the medieval city of Erice, our journey unfolds in the countryside of Segesta. Our morning walk introduces us to the enchanting Sicilan landscape, admist rolling hills, olive groves, orange and lemon trees, and expansive vineyards.
Following a lunch of Sicilian specialties, we proceed to the Archeological Park of Segesta. While the magnificent Doric temple is impressive, it is just one of the many highlights of a large archeological park. The semicircular theater, from which a vast and scenic panorama can be seen to the north, boasts a hilltop position on Mount Barbaro second to none.
After taking in this spectacular site of antiquity, we continue to the mountaintop city of Erice, where a cable car brings us the final stretch into town. We enjoy a late day walk along the cobblestone streets, and perhaps allow the aromas of neighborhood pastry shops entice us inside.
This evening we enjoy our first dinner together, and toast to our week ahead.
Hotel Elimo, Erice
Monte Cofano Nature Reserve; transfer to Menfi
Walk – easy to moderate, 4-5 hours, along country roads and trails; approximately 6 miles. Drive time approximately 30 minutes.
Today’s excursion brings us to the Monte Cofano Nature Reserve, offering miles of pristine coastline set against steep mountains. Our walk immerses us in one of Italy’s most beautiful coastal areas, now protected from future development. Here, classic Mediterranean vegetation flourishes in a profusion of yellow broom, rosemary, and capers above a turquoise sea.
We explore the coastline on foot, and weather permitting, take a swim in the Tyrrhenian Sea.
After our invigorating hike along the coast, we stop for lunch, and perhaps a refreshing granita (Italian slush), before continuing to La Foresteria, our home for the next two nights. Here we are enchanted by herb gardens, vineyards, locally-produced wine, and unparalleled Sicilian gastronomy.
This evening we enjoy a delicious seafood dinner at a beachfront restaurant.
La Foresteria, Menfi
Walk – easy to moderate, 3-4 hours, along country roads and trails; approximately 5.5 miles. Drive time approximately 2 hours.
This morning we arrive in Caltabellotta, one of the oldest hilltop villages in Sicily. Its uniquely prominent position on Mount Kratas has made it a significant and strategic place for more than two thousand years. Fought over, dominated, and destroyed over the years, Caltabellotta has always managed to regenerate itself. Here we enjoy a 5-6 mile walk with spectacular views of the sea and mountains.
After our walk we are rewarded with a visit to a local restaurant, where artisan-crafted pasta delights our senses. Following lunch we may choose to stretch our legs with a relaxing walk through the vineyards surrounding our hotel, or along the pristine beaches of the Mediterranean Sea.
We reconvene in the kitchen of our hotel, where we discover the secrets of Sicilian cooking with a demonstrative lesson using seasonal ingredients. Dinner tonight is al fresco on our hotel terrace.
La Foresteria, Menfi
Selinunte Archeological Park; Transfer to Castelbuono
Walk – easy to moderate, 2-3 hours, along trails; approximately 4 miles (optional afternoon walk, 2 miles). Drive time approximately 3.5 hours.
This morning we visit Selinunte, the largest archeological park in Europe, with extraordinary Greek temples and the remains of one of the largest cities in western Sicily.
After visiting this site of antiquity, we drive to our hilltop resort, Relais Santa Anastasia. From here we enjoy a spectacular view of the medieval village of Castelbuono, and many acres of vineyards and olive groves.
This afternoon, we enjoy a walk through the vineyards and a tour of the Abbazia Santa Anastasia Winery, known for its biodynamic approach to winemaking.
Tonight, we dine together at our hotel restaurant, Corte dell’Abate, where we are treated to fresh Mediterranean cuisine.
Relais Santa Anastasia, Castelbuono
Walk – moderate, 2-3 hours, along country roads and trails; approximately 3 miles. Drive time approximately 45 minutes.
Our morning hike in the interior Madonie Mountains reveals Sicily’s deeply rustic culture. Interior Sicily is a completely different world, and to many Sicilians, it’s the “true” Sicily of tiny mountain villages, farms, shepherds, and fresh-made cheeses. After our morning hike in the countryside, we enjoy a lunch at a favorite local spot, before returning to our inn.
This evening you may do as the Sicilians and stroll through the streets of Castelbuono, perhaps stopping for an aperitivo, before enjoying dinner on your own.
Relais Santa Anastasia, Castelbuono
Cefalù to Taormina
Walk – easy to moderate, 3 hours, along country roads and trails; approximately 6 miles. Drive time approximately 2.5 hours.
Our day begins with a walk through the Relais Santa Anastasia vineyards to the farming countryside above Cefalù, interspersed with small villas, orange groves, and private vegetable gardens.
In Cefalù, we might refresh with a lemon, coffee, or almond granita while strolling the medieval streets. We may also choose to visit the Cathedral-Basilica, or the Mandalisca Museum, and perhaps take a stroll on the beach before driving to Taormina.
Taormina also has some of the most spectacular views in the world – its Greek and Roman origins, medieval streets, and magnificent position overlooking the Ionian Sea have made it a favorite destination for centuries.
This evening you are free to walk through the winding streets of Taormina and dine at one of the many charming restaurants in town.
Hotel Imperiale, Taormina
Walk – 4-6 hours, moderate, along country roads and trails; approximately 8 miles. Drive time approximately 50 minutes.
Today we drive through graceful, dusky towns built of black lava stone to the lower slopes of Mt. Etna, the powerful volcano that the locals have learned to love despite its many spectacular eruptions. Our exciting hike takes us across lava fields from the 1983 eruption, and through pine forests and shady chestnut groves. Part of our hike is strenuous because we ascend on lava ash, which can make for rough footing, but the volcanic landscape is breathtaking. At the highest point of our hike, we have views down into a huge lava-covered valley, with Etna’s main crater visible above.
This evening we toast to our week in Sicily with a farewell dinner in Taormina, enjoying one last time the flavors of a region we have come to revere.
Hotel Imperiale, Taormina
Today we say ciao to this spectacular island and return home with stories of ancient times, astonishing scenery, and fine Italian wine. Transfers are provided to the airport at Catania after breakfast.
Please note that this is a typical itinerary, and actual activities may vary to take advantage of weather conditions, local events, and to allow serendipity to play a hand in your experience. Accommodations are as outlined in the itinerary, although we reserve the right to change these should the need arise.
- Sep 13–20, 2015
- May 14–21, 2016
- Sep 10–17, 2016
2015 Land Cost
$4,795 per person
Accommodations (hotels, tents, cruise cabins) are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability. If you reserve at least 120 days prior to departure, you may be eligible for a reduced or free single supplement.* This is generally limited to the first one or two solo travelers to reserve, and the reduction is outlined in the pricing for each trip. Please note, free or reduced single supplements are not combinable with other offers or promotions.
If you are traveling alone and wish to share accommodations, we will try to match you with a roommate of the same gender. If you reserve at least 120 days ahead and a roommate is not available, you will only be charged a “forced” single supplement in the amount of 50% of the standard single supplement* (unless otherwise noted in the detailed itinerary). Single accommodations are limited so you are encouraged to reserve early!
*This does not apply to cruises in the Galapagos Islands. Please see these trip pages for more details.
- Expert leadership
- All accommodations
- All transportation during the trip
- All meals except two dinners
- All activities as noted in the itinerary
Please complete the following information to request a reservation. A trip deposit of $500 per person is required to confirm your reservation (payable by check or major credit card). Once we receive your request we will contact you within one business day to confirm availability and answer any questions you may have.
About our guides
With a Boundless Journeys guide, your experience is that of friend and local adventurer. We believe strongly in working with local guides, experts in the areas to which we travel, and they hold the keys to unlocking the hidden delights of your chosen destination. Although you will never know they are at work – the mark of a truly great leader – our guides make magical things happen and add a dimension to your trip that you could not experience on your own.
Over the years we have forged bonds with some of the best guides in the world, and we typically work with a small team of guides in each region. You will be informed of the guide for your trip one month prior to your departure.
Alex Gullo: Since 1998, Alex has been a walking guide throughout Italy, from the Dolomites to Sicily, enjoying sharing Italy from all points of view - the natural beauty, the food, the wine, and the historical sites, with a particular look at the Italians of today. In return, he most enjoys the guests sharing a week of their life with him. Educated in the U.S. as well as Italy, he is a certified guide of historic monuments in certain Italian regions. He combines his charming personality with a vast knowledge to make our Sicilian adventures more than memorable.
Gianni Stanghellini: Gianni lives in Siena, a beautiful medieval town about one hour south of Florence. He has a Ph.D. in geology and has been a certified guide since 1999. Music has always been an important part of his life. He was the only member of his family who was not forced to study music, and he is the only one who is still playing! Gianni plays the flute and guitar in jazz and classical ensembles and began studying piano five years ago. Cooking and photography are among his other passions, which he combines artfully with guiding. Gianni enjoys sharing the history, culture, and natural beauty of Italy with guests, as well as much laughter.
Keegan Alagna: With an American mother and an Italian father, Keegan grew up in a bilingual home enriched with insights into two cultures and two countries. He grew up on a working farm in the Assisi countryside, and developed a passion for the natural world and the outdoors at a young age. During Keegan’s post-graduate work in geology at the Università di Perugia, his research often took him abroad where he consulted on volcanic phenomena. Keegan continues to pursue his interest in geology and the outdoors through participation in hiking programs with the Club Alpino Italiano, and in creating geology programs for the Italian schools. Keegan currently lives in Orvieto, and enjoys leading walking tours with a focus on Italy’s history, its natural wonders, and the Italian people.
What other Boundless Journeys guests have said about our Sicily guides:
"Actually we wanted to call and tell the people at Boundless Journeys that we had the time of our lives. I have to tell you THAT IT WAS EXCELLENT. Alex and his driver Fabrizio are such a great combination and did everything within their powers to accommodate us and give us a true Italian experience. Absolutely no corners were cut in terms of the activities and knowledge that they provided us with. This was a tailor-made trip that could not be duplicated by another tour company. This was not a tour, it was an experience." – V.M. & F. M., Katonah, NY
"This was definitely the best trip we have ever taken. I believe the primary reason for this was Alex Gullo. Not only was he unbelievably knowledgeable, but he was a kind and humorous walking companion. I would also like to mention our driver Fabrizio who, with Alex, made the perfect team." – D.P., Farmingville, NY
“We had a wonderful tour of Sicily, thank-you. Keegan was a GREAT guide - he certainly knows his history and his food!! AND now so do we. The hotels were great and the places we stayed were perfect. I feel as if I have a wonderful knowledge of Sicily now.” – R.O., New South Wales, Australia
"Thank you for yet another amazing adventure! The quality of service, guides, lodging, food, knowledge – is always top-notch. Alex and Gianni were a great team and did a flawless job tweaking the itinerary as needed to meet all of our needs and fulfill expectations." – H.H., Keene, NH
"Just imagine sitting in the chapel of an abbey atop a hill in the countryside while your guide plays Ave Maria on the flute...very moving experience! (and all this while sipping a great glass of wine). It doesn't get much better!" – J.M., Centerville, OH
Picture Yourself Here:
Walking and hiking along breathtaking coastal paths, on ancient trails, and over lava landscapes
Many of the finest ruins of Greek and Roman civilization
Turquoise seas, lemon groves, and cliff top gardens
Exciting Mediterranean cuisine, fine wines, and charming accommodations
- Sep 13–20, 2015
- May 14–21, 2016
- Sep 10–17, 2016
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“Culturally, physically, intellectually we had the time of our lives – and we’ve traveled a lot. But the difference was Boundless Journeys. Can’t wait to take another trip!“
- Verna M., Italy: Ancient Sicily
Latest Blog Posts About Italy
"Thank you, thank you for your most diligent efforts, meticulous attention to details, and most of all, patience with dozens of emails and calls, questions, and changes-of-mind. Jim and I are looking forward to a wonderful trip, knowing that everything is flawlessly planned. We appreciate all your efforts!"
- Alison Forbes, Botswana Private Adventure