Our special departure tours feature unique and exclusive vacations that are truly a once-in-a-lifetime opportunity.
Explore a selection of carefully planned itineraries that our tour experts have created choosing the best of the best from each destination.
Create the custom vacation of your dreams. You tell us where you want to go, and what you want to do, and we'll do the rest.
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 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’ hiking tour of ancient Sicily.
EXTEND YOUR TRIP – AEOLIAN ISLANDSThe seven islands that make up the Aeolian archipelago are known for their rocky coastlines, black sand beaches, thermal springs, fertile hillsides, and active volcanoes. Join us on a 5-day hiking adventure to explore the otherworldly landscapes and historic Mediterranean villages of Stromboli, Lipari, and Vulcano. Rooms available upon request. For more information, view the itinerary summary, call us at 1-800-941-8010 or email email@example.com.
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.
This evening we enjoy our first dinner together, and toast to our week ahead.
Residence San MartinoErice, Italy
The elegant Residence San Martino, located in the center of Erice, offers modern and comfortable apartments in a restored historic building. Two garden courtyards offer a relaxing place to sit and enjoy a coffee.
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 Casa Miregia, 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.
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.
This morning we go to a nearby inn to further immerse ourselves in Sicilian food culture. Set among herb gardens and an onsite vineyard, we'll learn about local gastronomy and take part in a cooking demonstration as we assist with our own lunch preparation. We'll dine al fresco on the terrace, enjoying fresh air and the lush surrounding landscape.
Our journey continues on 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 are rewarded with a visit to a local restaurant, where artisan-crafted pasta delights our senses in a well-deserved dinner. We return to our hotel in Menfi this evening.
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.
Upon arrival in Syracuse, we'll have a chance to settle in to our accommodations and enjoy the evening at our leisure. Explore the lovely neighborhood of Ortigia and choose from one of the many enticing restaurant options for dinner.
Grand Hotel OrtigiaSyracuse, Italy
Located on the coast, the Grand Hotel offers both a private beach and easy access to Ortigia’s historic streets. This 5-star hotel offers the best of Old World ambience, modern amenities, and world-class service.
Syracuse and Noto
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.
This afternoon, a leisurely boat ride along the coast gives us an opportunity to view the city from a new perspective, imagining how ancient sailors would have felt arriving at the coast of the vast metropolis.
We'll enjoy a stroll through the baroque town of Noto before dinner this evening, before returning to our hotel in Syracuse.
Catania and Taormina
Our day begins with a drive north to the city of Catania, known for baroque churches, colorful markets, and lively piazzas. We'll tour the historical highlights as well as visit local markets, along the way sampling street food steeped in tradition and flavors.
In the afternoon we continue our drive to Taormina, which 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 Villa BelvedereTaormina, Italy
In operation since 1902, the Hotel Villa Belvedere is conveniently located just a few minutes from the Public Botanic Garden and the pedestrian center of Taormina. Enjoy deluxe accommodations and views over the Bay of Nexos and 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.
Depart from Catania Airport
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 at Catania after breakfast. Some may choose to continue the adventure with a 5-day extension to the Aeolian Islands!
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.
Sep 29-Oct 6, 2019
Take over a date for your group! See "Make It Private" on Dates & Prices tab.
From $5,195 Per Person
First two reserved:$700
See single supplement policy below.
10+ Guests: $5,195 per person
9 or Fewer: from $5,495 per person
Make it Private price is based on Land Cost only, and a guarantee of the specified number of guests in double occupancy. For groups smaller than the numbers shown, or those requiring single occupancy, we reserve the right to adjust the per person price. Additionally, some trips have minimum group sizes. Please call 1-800-941-8010 for details.
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 may not apply to certain trips with unique accommodation arrangements. Please see specific trip information for more details.
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: 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 3-6 hours per day.
Palermo, Italy at 9:00 a.m.
Taormina, 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 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.
Maria grew up in the Sicilian city of Catania and also speaks the local dialect. She has traveled extensively herself and has previous experience working as an international aid worker. She is passionate about showing off the wonders and beauty of her beloved Sicily, as well as introducing guests to the culture, food, and way of life of Sicilian people.
She currently splits her time between Sicily and South Africa, where she is also a guide.
Michele spends his life moving between Rome and a small village in the central Apennines Mountains. After studying political science at university, he became a journalist, producing tourism guides and promoting environmental conservation. In 2004, he realized his dream of becoming a tour guide, combining his passion for communication, nature, and history. Michele spends the time he is not guiding exploring Rome with his wife. He looks forward to sharing his knowledge of Italy’s history and culture with you!
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.
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Easy to moderate walking and hiking, 4-6 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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