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.

Afloat in the center of the Mediterranean, for centuries Sicily has been the center of routes between north and south, and east and west. This parade of cultures has deposited fragments of language, architecture, art, cuisine, and religion that have made the island a reflection of Mediterranean history. This complexity of culture is only matched by stunning natural beauty and a tremendous diversity of landscape. We discover Sicily on hikes through rolling hills and valleys covered in olive trees and grape vines, on fiery Mt. Etna with its steep volcanic flanks covered in citrus orchards, and along many miles of turquoise coastline.

Day 1: Meet in Palermo and enjoy a morning walk in the breathtaking Iato Valley. Transfer to the medieval hilltop citadel of Erice.

Day 2: Walk along wild coastline in the Monte Cofano Nature Reserve, and enjoy a gourmet picnic in one of its beautiful coves. Visit the ancient Greek city of Segesta. Transfer to Menfi.

Day 3: Enjoy a walk in the hilltop village of Caltabellota with sweeping views of the seas and mountains. Visit Selinunte, the largest archeological park in Europe. Learn the secrets of Sicilian cuisine with a cooking class.

Days 4-5: Explore more of the Iato Valley at the Ficuzza Reserve. 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.

Days 6-7: Walk to the captivating seaside town of Cefalù with its medieval streets, picturesque coastline, and dominating Norman cathedral. Transfer to Taormina, Sicily's best-known resort, perched dramatically above the sea. Explore the flanks of Mount Etna, hiking over a recent lava flow and through shady chestnut and pine groves. Enjoy a picnic of local gourmet treats.

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.

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 the first day 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

Physical Activity
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 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
Erice, Italy

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
Menfi, Italy

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
Castelbuono, Italy

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 Monte Tauro
Taormina, Italy

Just a short walk from the town center and the Greco-Roman theater, this hotel overlooks the Sicilian sea and offers a view that spans from the Gulf of Naxos to Mt. Etna.

DAY 1
Iato Valley; Transfer to Erice

Walk – easy to moderate, 2-4 hours, along country roads and trails. Drive time approximately 1.5 hours.        

This morning after breakfast we take a walk in the beautiful Iato Valley, once a cradle of early Sicilian civilization, known for rice, wheat, cheese, and wine production. After immersing ourselves in the sights and smells of this lush countryside, we begin our drive towards Erice. Along the way we stop for a walk along the outskirts of the Archeological Park of Segesta, once a major city of the Elymian people, with its immense and well-preserved temple set in the quiet countryside.

This afternoon we continue to Erice, a charming medieval town with cobblestone streets and enticing pastry shops. 
Hotel Elimo, Erice

DAY 2 
Monte Cofano Nature Reserve; Archeological Park of Segesta; Transfer to Menfi

Walk – easy to moderate, 4-5 hours, along country roads and trails. Drive time approximately 30 minutes.

Today’s excursion brings us to the Monte Cofano Nature Reserve, 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, enjoy a mid-day picnic lunch, and if the weather cooperates, take a swim in the Tyrrhenian Sea.

This afternoon we enter the Archeological Park of Segesta. We take time to marvel at the solitary Doric temple and semicircular theater, from which a vast and scenic panorama can be seen to the north. The wonderful views made stage scenery unnecessary as the countryside provided an outstanding backdrop.

After taking in this spectacular site of antiquity, we continue to La Foresteria, our home for the next two nights. Here we will be enchanted by miles of vineyards and olive groves, tastings of locally produced wine, and unparalleled Sicilian gastronomy.
La Foresteria, Menfi

DAY 3 
Caltabellotta; Dispensa Winery

Walk – easy to moderate, 3-4 hours, along country roads and trails. Drive time approximately 2 hours.

This morning we arrive in Caltabellotta, one of the most ancient hilltop villages in Sicily. Its unique strong position on Mount Kratas has made it a significant and strategic place for over two thousand years. Fought over, dominated, and destroyed over the years Caltabellotta has always managed to survive and regenerate itself. Here we enjoy a 5.5 mile walk with spectacular views of the sea and mountains.

After our walk we are rewarded with a visit to the Dispensa Winery, owned by the Planeta family, who over the past 10 years has become Sicily's leading wine producer. Here the Planeta family concentrates on red wines. We enjoy a light lunch and tasting surrounded by the vineyards.

Following lunch we may choose to stretch our legs with a relaxing walk through the vineyards, or along the pristine beaches of the Mediterranean Sea.

This evening we discover the secrets of Sicilian cooking with a demonstrative lesson using ingredients linked with the season, before enjoying dinner at our hotel.
La Foresteria, Menfi

DAY 4
Selinunte Archeological Park; Ficuzza; Transfer to Castelbuono

Walk – easy to moderate, 4-5 hours, along trails. 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 depart Menfi and drive two hours to the Ficuzza Reserve, once a favorite hunting reserve for the kings and noblemen of Sicily. Here we follow a winding and scenic route of a former narrow-gauge railroad line. After a 3-4 hour walk, we drive the final 1.5 hours to our hilltop resort, Relais Santa Anastasia. From here we will enjoy a spectacular view of the medieval village of Castelbuono, and many acres of vineyards and olive groves.

This evening you may do as the Sicilian’s and stroll through the streets of Castelbuono, perhaps stopping for an aperitivo, before enjoying dinner on your own. 
Relais Santa Anastasia, Castelbuono

DAY 5
Madonie Mountains

Walk – moderate, 3-4 hours, along country roads and trails. 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 of Sicilian specialties before returning to our inn. 

This afternoon we may choose to spend some time getting to know the selections from the charming vineyards surrounding our hotel before heading into town for dinner. 
Relais Santa Anastasia, Castelbuono

DAY 6
Cefalù to Taormina

Walk – easy to moderate, 2-3 hours, along country roads and trails. Drive time approximately 2.5 hours.

We begin the day with a walk through the Relais Santa Anastasia vineyards and fields. We continue through 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 (Italian slush) 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 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 Monte Tauro, Taormina

DAY 7
Mount Etna

Walk – 4-6 hours, moderate, along country roads and trails. 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. Today is a highlight as we hike to a crater of Mt. Etna. Our exciting walk 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, and it is all uphill, 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 higher up to the left.

This evening we toast to our week in Sicily with a final farewell dinner in Taormina, enjoying one last time the flavors of a region we have come to revere.
Hotel Monte Tauro, Taormina

DAY 8 
Departure

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.

$4,595 per person

• Expert leadership
• All accommodations
• All transportation during the trip
• All meals except two dinners
• All activities as noted in the itinerary