10 Days Off the Beaten Path Tour of Southern Italy and Sicily

What to expect on this itinerary
Experience scenic hikes, exhilarating ziplines, intriguing caves with this immersive 10-day vacation to southern Italy and Sicily. Unique experiences and private day trips are included in this amazing and unforgettable vacation. Zipline in Castelmezzano, climb Mt. Vesuvius to enjoy incredible views of Naples, and venture to the Blue Grotto.
Customizable Itinerary
Naples – Explore Mt. Vesuvius
Your 10-day journey will begin when you land at Naples International Airport, where a private driver will greet and transfer you to your luxurious accommodation. Upon your arrival, you will have some time to settle in and relax before your guide leads you on an excursion to Mt. Vesuvius. Your guide will lead you up the side of the famous volcano, and once you are at the top, you will have an incredible view of Naples and the surrounding area.
What's Included:
Sorrento – Capri and the Blue Grotto
Matera – Adventures in Castelmezzano
Matera – The Unique Homes of Alberobello
Cosenza – Immersive Nature Hike
Catania – The Gorgeous Island of Sicily
Catania – Explore Syracuse and Ortigia
Palermo – Stroll through Enna
Palermo – The History of the Catacombs
Palermo – Departure
Trip Highlights
- Climb Mount Vesuvius to enjoy incredible views of the Bay of Naples
- Venture into the narrow opening of the legendary Blue Grotto and witness the amazing blue aura all around you
- Experience an exhilarating zipline ride in Castelmezzano with the Lucanian Dolomites in the background
- View the traditional homes of Alberobello that are known for their stone construction and cone-shaped roofs
- Discover the fresh air and natural beauty of Sila National Park during a hike through the area
- Traverse the bridge that connects Syracuse to the island of Ortigia, which is full of historic ruins and stunning views
- Enjoy the views in Enna as you explore the Enna Cathedral and Lombardy Castle
- Explore the winding twists and turns in the Capuchin Catacombs, home to the world’s largest collection of skeletons
Detailed Description
This journey through southern Italy and Sicily leads you to some of the most magnificent towns and villages in the area. Your exciting 10-day tour will begin when you land at Naples International Airport. In the afternoon, you will head out for a private tour of the impressive Mt. Vesuvius. The next morning, you will transfer to Sorrento. Here, you will enjoy an excursion to the stunning island of Capri, which will feature a memorable visit to the Blue Grotto.
The following day, you will continue to Matera. Along the way, you will stop in Castelmezzano for a zipline experience. The following morning, you will enjoy a day trip to the nearby town of Alberobello. During your private tour, you will get an up-close look at the unique trulli homes for which the town is known. After one more night in Matera, you will head to the age-old city of Cosenza. After having some time to get acquainted with your new hotel, you will indulge in a scenic hike through Sila National Park.
A relaxing private transfer and a scenic ferry ride will be in store for you the following day as you make your way to the island of Sicily. By the end of the day, you will reach your hotel in the delightful city of Catania. The next morning, you will journey to Syracuse and the island of Ortigia. Syracuse is a UNESCO World Heritage Site, and during your private tour, you will get to see and explore ancient ruins. On the next day of your trip, you will transfer to your final destination of Palermo. During your drive through the countryside, you will stop for a tour in the city of Enna, which is located over 3,000 feet above sea level. After your first night in Palermo, you will explore the history of the city with a private visit to the Capuchin Catacombs.
Starting Price
$3,600 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.
Verified Traveler Reviews
Based on 979 reviews
Zicasso’s travel professional crafted an unforgettable Sicily trip for our group of seven. After discussing our preferences, she designed a flawless itinerary, incorporating unique experiences that became trip highlights. Her communication was exceptional, with prompt responses to our questions before the trip and daily updates for the next day's activities, including driver and guide details, which were incredibly helpful.
We stayed at superb hotels in Taormina, Agrigento, Palermo, and Cefalù, each with stunning views and private tours. Sicily’s warm, hospitable people stood out compared to other European destinations. At our hotel on Via Leonardo da Vinci in Taormina, the staff greeted us warmly, setting a perfect tone. Other stops included Mount Etna, Erice, Castelbuono, and Savoca. All of these locations were great, but don't miss Castelbuono!
Two standout experiences were private meals with families. Near Erice, a chef and his family welcomed us into their sea-view home, preparing amazing Sicilian meals that felt like dining with family. In Palermo, another home chef and her husband created a similarly memorable evening, with lots of great conversation and stories.
Every driver was professional, friendly, and informative, while our guides — often archaeologists or historians — were engaging and knowledgeable.
Highlights included a welcome dinner in Taormina, a farm cooking class, two wine tours with lunch, a Mount Etna hike, a Valley of the Greek Temples tour, town and village tours, cheese and pastry tastings near Cefalù, and a farewell dinner. The Godfather tour in Savoca was special, with our guide introducing us to a local who played Apollonia’s mother, waving from her balcony.
Our travel professional's meticulous planning and personal touches made this trip extraordinary. Thanks to Zicasso for matching us with the tour company and we highly recommend them for a perfect Sicilian/Italian adventure!
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The travel company and staff were excellent. The trip coordinators accompanied us through the trip via WhatsApp. They were terrific. The service was top-notch, including the drivers, tour guides, and accommodations.
The one thing I would change about the trip is to have longer stays in each city visited. Moving to a new hotel every two nights prevented us from really enjoying each city we visited. I would also forgo Palermo and substitute a smaller city like Noto or Agrigento. But again, the itinerary was based on my interests and time. It is not an indication of the tour company's abilities. However, it may be good for the agency to suggest longer stays to other customers. Otherwise, we had a great trip and once again, I have recommended Zicasso and the tour company to family and friends.
Thank you again for a great time!
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I was connected with the travel company through Zicasso. What an amazing trip! Many thanks to our travel designer of the travel company!!!
Our travel designer and her expert team planned a trip to Sicily for my husband and I, my siblings, and my sister-in-law. We were six and everything about the trip was executed beautifully and with great attention to every detail.
We chose to go to Taormina, Cefalù, Palermo, and Ortigia Island, flying direct in and out of Catania. Our travel designer arranged all transfers by private van for the six of us and we never had to worry where or when we were going anywhere. She was able to make changes on the spot and accommodate our every wish.
Planning the trip was so easy, as she was available to chat with me on the weekends to answer questions and clarify details. She even made dinner reservations in every city. I cannot say enough about her willingness to be available and the choices she helped us make. From the terrific winery near Mount Etna to a drive up Etna, guided tours (we had an incredibly fabulous art historian showing us the churches of Palermo), a day at leisure on the beaches of Cefalù, and an amazing cooking class in Palermo, where we learned about and visited the markets, and made pasta and cannoli, every experience was better than the one before it.
We definitely recommend, with five stars, the travel company. Have them plan your trip to Italy! This was my first time back to Europe since 2004 and it was stellar!
I surely will use this company when I plan new trips to Italy, and Zicasso as well!
When we were trying to decide where to go, we chatted with travel partners in several European destinations. Zicasso chooses the best of the best and our experiences with each of them was exceptional!
We will be back to Zicasso when we travel to other destinations!!
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Zicasso's travel designer did an excellent job planning a three-week trip for us in Naples, the Amalfi Coast, Capri, and several cities in Sicily. We appreciate that she met with us by Zoom on two occasions to tweak the draft itinerary to be sure it was the trip we were looking for. She listened to us and created an itinerary that met all of our needs.
The guides, drivers, and accommodations were excellent. The guides all spoke excellent English, were easy to understand, and obviously well educated and informed about the details of the history, architecture, art, and culture of each site we visited. The experience was educational, in addition to just enjoying the beauty of Southern Italy and Sicily.
We had one potentially disruptive event when a labor strike caused a cancellation of our flight from Naples to Sicily. Her team did an amazing job of creating an alternative, involving going by train to Rome, then catching a plane from Rome to Catania, and our arrival was only a few hours later than the original itinerary. Our word to describe their creative plan is "Brilliant."
Overall it was a great and memorable experience, thanks to the excellent recommendations, planning, and making all of the arrangements for our visit.
We will have no hesitation to recommend her and her team to our friends and family. Thank you for arranging for us to benefit from their incredible services.
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I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.
Trip Planning:
As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.
Transportation and travel between locations:
Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.
One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.
Venice:
Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.
The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.
Florence:
As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.
While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.
Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.
Day trip to Pisa:
The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.
The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.
Rome:
Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.
Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.
The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.
The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.
The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.
The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.
Sorrento:
We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.
During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.
Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.
On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.
Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.
Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.
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This was a superb trip that allowed us to combine personal visits to Taormina and Syracuse with a pre-planned group meeting in Catania. Planning and communication were excellent, supported by an app that let us easily view our itinerary, complete with phone numbers for the drivers, hotels, and the tour operator contacts.
The hotels were perfect! They were wonderfully located, with impeccable service in Taormina and Syracuse. Our excursions were private and diverse, and allowed us to combine culture, foodie interests, and free time. The guides were top-notch, knowledgeable, and flexible.
We especially loved seeing the smaller towns of Sicily; Militello, Ragusa, Aci Castello, and Modica. We even arrived in one small town during their annual festival.
We had a dedicated driver for our trip who was, himself, a treasure; always on time, always ready to adjust to changes, and a delightful personality.
This was such a good experience that we have selected Zicasso's tour operator to book another Italy trip next year.
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