Culture, Tradition & Beauty of Southern Italy Tour

What to expect on this itinerary
This is the Italy of ruin and prestige, artistry and strongholds, an Italy steeped in culture deriving from ancient life. Your 9-day custom-tailored Southern Italy tour immerses you in majesty from Naples to Palermo, connecting the heritage of the past with the traditions of the present. Greek temples tower over rocky promontories. Roman villas provide insight into the wealth and opulence of emperors. Lush citrus groves grow on terraces stretching beneath limestone cliffs, and the Mediterranean Sea shines with turquoise water against gold-sand beaches. Follow the trails of history to discover the welcoming traditions of Southern Italy.
Customizable Itinerary
Positano – Reaching Southern Italy
Naples is a city rich in history both inside the city center and bordering the harbor. Lavish churches overlook cobblestone streets, and the Castel dell’Ovo stands proudly at the edge of a rocky promontory with roots dating back to the 6th century BC. Your flight lands and Naples International Airport where you meet your private transfer. On the outskirts of the bustling city, you find the aroma of citrus emanating from lemon groves thriving in the Mediterranean climate. The turquoise sea laps at the coastline of the Bay of Naples.
The scent of rich espresso drifts out of small corner cafes. You stop at the entrance to Pompeii Archeological Park as your introduction to the marvelous history of Southern Italy. Your guide meets you at the entrance eager to show you the highlights of the Roman port city once covered in ash and pumice from the volcanic eruption of Mount Vesuvius in 79 AD. Excavations have revealed that the layers of ash have kept the city intact, complete with sailor hotels, bars, public baths, and taverns. The fragrance of rich soil rises from the Roman Forum.
Portions of pillars frame the piazza leading to the Basilica, which once housed the city’s courts. As you stroll along the cobbled streets, your guide points out homes in which frescoes continue to decorate the walls. Pillars crowned with Corinthian capitals flank the House of Meander. The interior contains frescoes depicting scenes from Homer’s Iliad. A wooden roof hovers over the small temple in the corner of the atrium. You are not only seeing ancient history but walking in the footsteps of a citizen of Pompeii, with the image of Mount Vesuvius’s conical peak ornamenting the sky on the horizon.
What's Included:
Positano – Traversing the Gulf of Salerno
Positano – Island in the Sun
Palermo – Beyond the Toe of Italy’s Boot
Agrigento – A Rich History of Tradition
Taormina – The Baroque in Sicily
Taormina – A Day on the Cliff
Catania – Holding to Tradition
Catania – Out of Time In Antiquity
Trip Highlights
- Discover the stunning preservation of ancient streets, frescoes, and architecture in famous Pompeii
- Wander along the gorgeous shoreline of the Amalfi Coast for an unforgettable mixture of landscape and sea before witnessing the glowing Emerald Cave
- Explore one of the best-preserved collection of Greek temples in all of Italy in the Valley of the Temples outside Agrigento
- Experience a town frozen in time at Forza d’Agro, where Sicilian tradition in both culture, architecture, daily life remains strong
- Stroll through the combination of ancient foundations and contemporary culture in Syracuse
- Tour the medieval cobblestone streets of the triangular shaped town of Erice, located at the top of a Sicilian mountain
- Trek the trails of Capri for remarkable views of the undulating mountains and steep coastal cliffs
- Linger amongst the beautiful baroque architecture in the towns of Noto and Taormina for insight into the history and culture of the past and present
Detailed Description
Southern Italy blends the cultures of the past, which has effortlessly shaped the contemporary traditions associated with the Campania region and Sicily. Your 9-day historical exploration is meant for amateur archeologists and enthusiastic anthropologists; whether a fan of Italian heritage or a lover of coastal landscape, you will discover charm in a daily life enriched by the stunning scenery and adorned with unforgettable history. Your discovery begins with your arrival at Naples International Airport. Your private transfer meets you at baggage claim and escorts you to the entrance of ancient Pompeii. Meet your guide and follow the streets of the preserved city to find villas, restaurants, mosaics, and frescoes captured in time before continuing to the town of Positano.
The following day, you have a private driver available to take you along the scenic road traversing the Amalfi Coast. Visit the famous towns of Ravello and Amalfi, along with the lesser-known seaside towns of Vietri sul Mare and Conca dei Marini, for an encompassing image of the seaside culture and historical lanes around the coastline. Then, you board a ferry to the island of Capri. Discover the respective villas of emperor Tiberius and Augustus or trek the trails crisscrossing the island for views of the Faraglioni Stacks before returning to Positano. The following day, you have a private transfer to the Naples airport for your brief flight to Palermo.
Meet your guide and transfer at baggage claim to tour the historic city blending Norman, Arab, Spanish, and Italian cultures through architecture and tradition. Next, you travel to the medieval town of Erice, located on a mountaintop overlooking the shoreline. Wander the cobblestone streets, arches, and ramparts before visiting the Valley of the Temples outside Agrigento. The archeological site contains one of the largest collections of Greek temple ruins outside of Greece. You discover the splendor of the Baroque period in Sicily by strolling the streets of Noto. Step back in history with the preserved ancient sites at the heart of Syracuse before settling in the seaside town of Taormina.
The day is at your leisure in Taormina to enjoy the surrounding possibilities. Venture to Mount Etna to hike the trails on the active volcano or visit the nearby beaches to relax in the Mediterranean sun. You could also linger around Taormina to bask in the café lifestyle of the vibrant streets. Then, your private transfer leads you to Forza d’Agro to experience the true, unspoiled culture of Sicily. Continue to the contemporary city of Catania to tour the baroque architecture. On the final day, your private transfer meets you in the hotel lobby and escorts you to the Catania airport for your flight home.
Starting Price
$4,100 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
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 641 reviews
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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My husband and I were thrilled with our recent trip to Italy that Zicasso’s travel designer put together. We began by attending a family friend’s wedding, held in Ravello, on the Amalfi Coast. Due to my husband’s mobility issues, we were met by a driver and headed to the Amalfi Coast. The driver was first class and the trip was very comfortable.
After the wedding festivities, we were able to have the most wonderful experiences visiting the towns of Amalfi and Positano, and our base for one week was in beautiful Sorrento. We attended a cooking class and enjoyed eating what we prepared. We had in-depth learning opportunities in Naples and Sorrento. Every guide we had spoke excellent English and was so knowledgeable. We especially enjoyed Pompeii! A super-fun day was had on the small group tour of Capri. The crew was fantastic and very accommodating in consideration of my husband’s mobility issues.
From beginning to end everything went well. The use of a messaging app was great for making sure everyone was on the same page.
The only thing that was a disappointment was the pizza in Naples. It wasn’t the best.
The hotel in Sorrento was phenomenal - it couldn’t have been better. The view of Mt. Vesuvius from our balcony helped create memories we will have forever. The hotel in Rome was also very nice. It was right in the middle of the main attractions.
We are very happy with our experience with this travel company and would not hesitate to recommend it!
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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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Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.
Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.
Our tour guides and drivers were excellent.
My only regret is that we only had 10 days to explore Sicily as there was so much more to see!
Our agent did a yeoman's job helping us plan this trip.
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We had a wonderful trip. We started off dealing with a canceled train on the arrival day due to a strike, but you had back-up train tickets even before we arrived in Rome. The drivers were all on time and very courteous. The drivers in Tuscany and the Amalfi Coast were exceptional. The driver from Naples to Sorrento was very nice and helpful; however, his car smelled of smoke and was not very clean. The hotels in Florence and Rome were great, but the Sorrento hotel was not as nice. You spoiled us with the standards in Florence and Rome.
Our one suggestion for Capri involves time management. While no one can predict the crowds, I would suggest notifying your travelers that getting to Anacapri will take a long time, either by taxi or bus. Our group from the boat took an hour and 20 minutes to get to Anacapri by bus. The trip back to Marina Grande was an hour. There are no direct buses to and from Anacapri and Marina Piccola. My wife and I then walked to Marina Piccola since waiting for a bus would have made us late for the boat. The others in the group waited for taxis in Anacapri and we still beat them back to the boat, even though we walked from Marina Grande to Marina Piccola. Four hours is just not enough time to go up to Anacapri to ride the chair lift and get back. This was the only time we felt rushed during our trip.
We would like to thank you for a wonderful trip and would recommend your agency to others.
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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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