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 Italy hiking tour unfolds as we leave the bustle of Palermo and head to the countryside, where we spend our days exploring the historic hilltops and breathtaking coastlines of Erice, Monte Cofano, and Caltabellotta, before departing for the eastern half of the island. Our journey is accented with tastings from the surrounding vineyards, experiencing Sicilian gastronomy, and cultural excursions that take us into the heart of Sicilian history.
Fascinating ruins of early civilizations, beautiful coastal paths above the turquoise waters of the Mediterranean, and food, glorious food, are yours to discover on Boundless Journeys’ coast to coast tour of Sicily.
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Archeological Park of Segesta; Transfer to Erice
Our journey unfolds in the Archeological Park of Segesta. While its magnificent Doric temple is impressive, it is just one of the many highlights of this large outdoor museum. 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.
A short transfer brings us to our resort, where we we enjoy dinner together and toast to our week ahead.
Venere di Erice ResortErice, Italy
The 4-star Venere di Erice Resort is located on the slopes of Monte Erice, with a breathtaking view of the Gulf of Bonagia. This boutique hotel offers a panoramic terrace, outdoor pool, solarium, spa, and a seaview restaurant where you can taste Sicilian delights.
Monte Cofano Nature Reserve
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 our boutique hotel in Menfi. Here, we are enchanted by unparalleled Sicilian gastronomy for our evening meal.
Casa MiregiaMenfi, Italy
Casa Miregia offers Sicilian hospitality and complete relaxation amid olive trees, vineyards, and an onsite garden. Relax by the pool, or simply take in the tranquil oasis of this rural property located only 10 minutes from the coast.
Caltabellotta
This morning we proceed to 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 2,000 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 join a Sicilian chef for a demonstrative cooking class using seasonal ingredients. We dine on the exquisite meal created, complimented by regional wines.
Valley of the Temples
This morning we set out for Syracuse, on the southeastern coast of Sicily. Along the way, we stop in Agrigento to visit the Valley of the Temples, one of the most famous archaeological sites in the world. A local guide will regale us with tales of early Greek civilization in Sicily, and we'll tour the picturesque landscape marked by olive trees, almond groves, and temples — including the well-preserved Temple of Concordia, and the ruins of the ancient city of Akragas.
Late in the afternoon we arrive in Modica where we have a chance to settle in at our accommodations and enjoy the evening at our leisure.
San Giorgio Modica HotelModica, Italy
The San Giorgio Hotel is a charming boutique accommodation nestled in the heart of Modica, Italy. Its prime location offers easy access to the town’s historic sites, local attractions, and authentic Sicilian culture.
Ragusa and Modica
Today we discover the beautiful baroque cities of Ragusa and Modica. We begin the day with a walk through Cava Santa Domenica Park. Our trail meanders through small terraces, streams, waterfalls, ancient quarries, caves, and kilns used to reduce stone to lime. The environment is truly suggestive. All around are lush walnut, fig, almond, olive and carob trees. Our hike ends in the lovely city of Ragusa, where we have time to explore and enjoy lunch with local cheeses.
In the afternoon, back in Modica, we visit an ancient chocolate factory. The flavors of the Ragusa cheese we tasted earlier will melt with the sweetness of the renowned Modica chocolate.
This evening we dine together in town.
Syracuse and Taormina
We begin today with a private cultural tour of Syracuse, which was the largest city of the ancient world during the Greek Classical Period — surpassing even Athens and Corinth at the time! We'll visit the Neapolis Archaeological Park and its famous Greek theater, explore the chic neighborhood of Ortigia, and learn about the significant role the city played as one of the early major powers in the Mediterranean.
Early in the afternoon, we transfer to Taormina. This elegant small town 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.
Hotel Villa DiodoroTaormina, Italy
Hotel Villa Diodoro features a hillside position and an outdoor pool with panoramic sea views, a 5-minute walk from the historical center of Taormina. Its elegant restaurant serves Sicilian and international dishes.
Mount Etna
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 hike takes us across lava fields from the 1983 eruption, and through pine forests and shady chestnut groves. We ascend on lava ash, which can make for challenging 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 us.
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.
Departure
Today we say ciao to this spectacular island and return home with stories of ancient times, astonishing scenery, and fine Italian wine. A transfer is provided to the airport in Catania after breakfast.
Please note that this is a typical itinerary, and actual activities may vary due to 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 or the order visited should the need arise.
8 Days
Sep 14-21, 2025
From $5,495 Per Person
First two reserved:$295
Additional:$795
See single supplement policy below.
May 10-17, 2026
Sep 14-21, 2026
$5,495 Per Person
Pricing shown is for 2025; for 2026 departures reserved before 2026 pricing is available, pricing will be protected up to a 5% increase.
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Call for pricing: 1 800 941 8010 or email info@boundlessjourneys.com
SINGLE SUPPLEMENT: Accommodations are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability.
Single Supplement for Scheduled Group Departures. 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. 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 request a roommate but one is not available, you will receive a $500 reduction from the standard single supplement (unless otherwise noted in the detailed itinerary for your specific trip).
Single Supplement for Custom Tours. Custom Tour prices are generally based on two or more participants; therefore, single supplements for “solo” Custom Tours will vary and are available upon request.
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. Italy: Splendors of 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 3-6 hours per day.
Palermo, Italy at 9:00 a.m.
Catania, Italy; after breakfast.
Most Convenient Airport: 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.
The climate is typically Mediterranean, with hot summers, and short, mild winters. The weather in late spring and early fall is usually very pleasant, with daytime temperatures that range from low 60s to upper 80s, and the 50s and 60s at night. While these months are not in Italy's "rainy season" there can be cool breezes or showers at any time. Please come prepared to walk rain or shine. We will always walk unless weather conditions make it dangerous to do so.
You may obtain more detailed weather information on www.weatherbase.com.
Sicily
High: 72 Low: 61
High: 81 Low: 72
Sicily has a pleasant sunny climate and the spring and fall months tend to be the best times to visit, avoiding the very hot summer months and peak tourist season. Mountainous areas can be surprisingly cool, especially in the evening. A swim in the sea is possible from April to October, with water temperatures increasing throughout the summer months.
Sicilian cuisine is built upon influences from Turkey, Greece, and the Middle East. This blend lends a slightly spicy base to many dishes. While fresh fish and seafood specialties are the most common, you will also find rabbit, game, and other dishes when in season. Delicacies such as fish-stuffed ravioli served with prawn sauce, chicken or veal marsala, seafood stews, fish gnocchi with sun-dried tomatoes, or shrimp flan with red wine sauce are but a few of the regional specialties you might enjoy.
Because the Italian kitchen serves only fresh local ingredients, menu choices are limited at dinners to ensure prompt and efficient service for our groups. As a general rule, Europeans tend to eat at or after 8 p.m. Dinner is served in several courses starting with an antipasto (appetizer) and followed by a primi (usually pasta or risotto), a secondo (a meat or fish dish), and dessert. Dinners can last up to two hours. Breakfast, served at the hotel, is typically buffet style including bread, jams and butter, pastries, juices, and yogurt. Eggs, cheese, cold cuts, and fruit may sometimes be available. Lunches vary from pasta and salad at simple country trattorias, to picnics, to panini sandwiches at cafés.
Two dinners are not included in your trip cost, as we believe that venturing out on your own is an important part of discovering a new culture and cuisine. Your guide will be happy to make recommendations. Vegetarians can easily be accommodated.
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.
We love Italy — its scents, flavors, scenery, and people. The landscapes stir the soul, with sweeping vistas of vineyard-cloaked hills, stately cypress trees, and gnarled olive groves grounded in red earth. The Puglia region, located in the heel of Italy’s...
Easy to moderate walking and hiking, 3-6 hours per day.
This trip can be your own adventure by taking over one of our scheduled dates, or we can request a fresh one.
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