In the Footsteps of Italian History Tour: From Antiquity to Contemporary

What to expect on this itinerary
The Second World War forever changed Europe, from Britain in the north to Sicily in the south, leaving trails in the form of stories now illuminated in Italy, leading you from Rome to the Amalfi Coast. Your custom tailored tour brings history to life, from the Italian beaches on which the allies landed to the former German Embassy in Rome that the SS turned into a jail, imprisoning members of the Italian Resistance. From occupation to liberation, you will explore and discover the unique stories of Italy preserved on the shores, in the hills, and exhibited in local museums.
Customizable Itinerary
Rome – A World of the Classics
Rome is a city that has watched the world change for more than 2,000 years, evolving with new times, new kingdoms, and new ways of thinking. With each large-scale change in the world, the city of Rome remains constant, giving it the nickname the “Eternal City.” Your flight lands in Fiumicino International Airport. Your private transfer meets you at baggage claim and escorts you into the historic city center to your hotel. The marble bath and large terrace provide perfect introductions into the beauty of Rome’s elegant past with a hint of the types of lavish embellishments the Roman aristocracy enjoyed.
After settling into the comforts of your room and the view from your balcony overlooking the Seven Hills of Rome, you meet your private guide in the hotel lobby for an introductory tour. The iconic images of Rome come to life, beginning with the Trevi Fountain. The 18th-century adornment stands on the back of Palazzo Poli with a height of 86 feet tall and more than 160 feet wide. The sound of trickling water emanates from the widespread waterfall falling into the waiting, iridescent pool. Oceanus stands at the center of the fountain surveying the water atop his shell chariot. People stand with their backs to the fountain and throw coins over their left shoulder. They listen for the splash of the coin hitting the water, which, according to legend, means the person will return to Rome.
What's Included:
Rome – Partisans and Troops
Anzio – Landings and Liberations
Monte Cassino – In the Air of Paratroopers
Positano – History in the Halls
Positano – Italy’s Former Capital
Positano – Leisure on the Coastline
Positano – Leaving History Behind
Trip Highlights
- Experience the thrill of walking on the beaches the Allies landed on during their operations to take back Italy from German forces in World War II
- Traverse the renovated grounds of the Abbey at Montecassino, home to a decisive battle and bombing due to its proximity to the Gustav Line
- Wander the opulent grounds of Caserta Palace where Germany signed their unconditional surrender, bringing the European war to an end
- Discover the unique stories and tumultuous history of Rome during World War II in the Museum of the Liberation of Rome
- Relish a day at leisure in the beauty of the Amalfi Coast to enjoy the Mediterranean Sea, gorgeous landscape, and visit to ancient Pompeii
- Traverse the Amalfi Coast to reach the city of Salerno, the temporary capital of Italy before the liberation of Rome
- Tour the beauty of Rome with a private guide for insight into the opulent history of the Eternal City, highlighting the importance of what was worth saving from Nazi destruction
Detailed Description
Your 8-day tour takes you from Rome to the Amalfi Coast, visiting the beaches of Anzio and the Abbey of Montecassino in the footsteps of large battles and hidden retaliations led by the Italian Resistance. The landscape, accompanied by museum galleries, offers unique insight into the true stories of the war fought across Europe. The journey begins with your arrival in Rome at Fiumicino Airport. Your private transfer escorts you to an opulent hotel that was once a palace in the historic city center.
Follow your guide on a half-day tour of Rome’s historic beauty highlighting the importance of the art, architecture, and culture in need of saving from occupation. The next day, you visit the Museum of the Liberation of Rome on Via Tasso for a detailed perspective of what was once the German Embassy before it became the SS headquarters. Your private transfer meets you at the hotel the next morning and escorts you to the coast at Anzio, where the Allied forces staged their landing. Explore the caves, Museum of Anzio, and American Monumental Cemetery before embarking on a private cruise for a view of the shoreline in an attempt to see the coast as the Allies had.
Next, you transfer to Montecassino to tour the abbey once bombed by Allied forces in an attempt to break through the Gustav Line. Your guide will point out the German stronghold, along with the elements of the abbey restructured over the decades. Then, you travel south to Naples, stopping for a tour of the Palace of Caserta, where the Germans signed their unconditional surrender. Reach your luxurious palace-style accommodations in Positano to enjoy the remainder of the day at your leisure.
Next, you travel the length of the Amalfi Coast with a guide, visiting small towns at your whim and pleasure before reaching the Salerno. The coastal city once served as the capital of Italy before the liberation of Rome. The following day is at your leisure to enjoy, relax, and discover at your preferred pace. Traverse the streets of Positano, venture to the island of Capri, or wander the vast grounds of the ancient city of Pompeii. On the final day, your private transfer meets you at the hotel in Positano and escorts you to Naples International Airport for your flight home.
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
- 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 716 reviews
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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A number of items on the itinerary were not provided. We did not go to the puppet museum. The food tour was poor. We did not stop at a town on the Amalfi Coast. The hotels were nice.
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Zicasso matched us up with two Italian travel agencies. We provided our dates of travel and approximate travel budget per person. Each agency gave us a preliminary itinerary. We were able to request changes to the itinerary and then chose the one that we preferred. The communication through the Zicasso website was easy and comprehensive.
Our entire trip went off without a single problem. We stayed at a very nice apartment in Rome, 1,000 feet from the Colosseum. We had very knowledgeable private tour guides for the Colosseum and the Vatican, allowing us to skip all of the entrance lines. We had private transfers from the airport to the apartment and from the apartment to the train station. We took a train from Rome to Naples and had another private transfer to a very nice hotel in Ravello. We did a private boat tour of the Amalfi Coast with a captain and a first mate. Drinks and snacks were included. We did a guided hike, which ended at a farm-to-table lunch. We spent a morning in Pompeii, followed by a local wine tasting and lunch.
Every part of the vacation exceeded our expectations. The accommodations were fantastic. The planned activities were just what we were looking for. We still had enough free time to explore on our own and choose which restaurants we wanted to eat at each evening. I feel like we got a great deal for what we paid and would definitely book a vacation through Zicasso again.
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The travel company did a fantastic job planning our Italian vacation to the Amalfi and Sorrento coasts. The hotel in Positano was breathtaking. The excursions that Zicasso's travel designer recommended were fantastic. The cooking class in the hills overlooking the coast was amazing. Our travel plans changed due to airline difficulties and she was incredibly helpful in making adjustments on the fly to ensure our trip went as smoothly as possible.
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Zicasso's travel specialist asked for our interests, to which we replied history, art, food, and wine. When queried about accommodations, our preferences were that they have character and be varied. Our expectations were exceeded.
We were two couples who had a spectacular survey trip of Italy. Our agent addressed our request for history by arranging private tours with expert guides. We visited multiple eras: ancient times at the Egyptian Museum in Turin and the Colosseum in Rome; medieval times at the Medici palazzos; Byzantine times with views of the frescoes in Puglia; and modern history during a delightful food tour of Turin that featured historical cafés renowned for their political meetings and plotting.
We indulged in a smorgasbord of art and history, as it is readily available wherever you journey in Italy. The guides and drivers were knowledgeable, pointing out treasures in the palazzos, the Vatican, the public squares, cafés, the cathedrals, and churches. Food tours featured cheese, capicola and truffle tasting. Multiple types of wines and vineyards were sampled, the settings varied and the offerings enjoyed.
Accommodations could not have been better chosen. We enjoyed staying at a converted fortified monastery and a historic 16th-century palace. We appreciated the sunset over Turin from the upper deck of the hotel and enjoyed hidden privacy in Rome in our suites.
During the trip, our guide shepherded this complex trip and promptly addressed any issues that occurred (delayed trains and coordinating tour guides). Unequivocally, each tour was unique and well picked by our agent. We strongly recommend this agency to help you have a fantastic trip to Italy!
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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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