Discovering Italy and Spain: Special Off the Beaten Path Tour

What to expect on this itinerary
Expect marvels and majesty when stepping away from the well-worn path in search of unexpected wonders during this personalized 12-day tour of Italy and Spain. The medieval towns are hidden on the hills of Spain shine with the influence of Roman settlements and Moorish rule. Villages in Italy lead to remarkable churches that shine with gilded mosaics. Uncover the hidden allures of Spain and Italy that bring the distinctive cultures, delicious cuisines, and specific myths of each country into the spotlight.
Customizable Itinerary
Madrid – Introduction to the Culture
The energetic capital of Spain captures the country’s surrounding culture amid the city’s Royal Palace, Prado Museum, and lavish parks. Your private transfer will greet you at Adolfo Suárez Madrid-Barajas Airport upon your arrival and escort you to your luxurious accommodation. Your first day in Spain will offer you a unique view of the capital by highlighting the charms of the hidden gems that are tucked into the shadows of the mainstream sites across Madrid. The Naval Museum on Paseo del Prado hosts the oldest known map of America, which was discovered in a Paris bookshop in the mid-19th century. The map was drawn around the year 1500 by Juan de la Cosa, who sailed with Cristopher Columbus.
What's Included:
Madrid – Off-the-Beaten-Path Adventures
Madrid – The Palacio Real in Aranjuez
Madrid – The Medieval Charm of Cuenca
Madrid – The Exterior of Extremadura
Madrid – Visit Alcalá de Henares
Avellino – Relaxing Day in Avellino
Avellino – The Grounds of Caserta Palace
Rome – The Reach of Ancient Rome
Rome – Spend the Day in Cerveteri
Rome – The Medieval Lanes of Orvieto
Rome – Depart for Home
Trip Highlights
- Uncover the magnificent ancient Etruscan necropolis of Cerveteri to find reproductions of daily life in the reliefs that decorate noble family catacombs
- Wander the enchanting landscape of Spain’s Extremadura region and visit the medieval hilltop towns of Cáceres and Mérida
- Explore the opulent gardens, galleries, halls, and impressive stairway of the Caserta Palace, which is one of the largest royal complexes in the world
- Traverse the remarkably preserved Roman port city of Ostia Antica to find majestic mosaics, statues, and the remnants of life in ancient Rome
- Discover the Roman ruins of Segovia with the stunning aqueduct that runs through the heart of the Spanish city
- Visit the birthplace of Miguel de Cervantes in Alcalá de Henares and witness the statues that were dedicated to his work and life
- View the sensational gilded mosaics of Orvieto, which is a town that is halfway between Rome and Florence
- Stroll the sensational streets and elegant plazas of Aranjuez before spending time in the glitzy halls and galleries
Detailed Description
You can uncover the lesser-known gems of Europe during this 12-day off-the-beaten-path tour of Spain and Italy. Your handmade experience will highlight the overlooked marvels of the countryside and the charismatic monuments that are often missed inside the big cities. You will travel between towns and villages and between restaurants and cafes for an authentic view of life.
Spain is a country that is known for its passion and sophistication. The locals are devoted to enjoying life’s daily pleasures. You will arrive in Madrid and use the capital city as your base for six nights. The towns of Segovia, Aranjuez, Cuenca, and Alcalá de Henares all share an enchanting ambiance that stems from their medieval architecture and pace of life. The untouched region of Extremadura hosts hilltop villages that are imbued with the history of Roman settlements. When visiting the different towns, you can travel at your own pace, sample the local dishes, explore the cobblestone lanes, and delight in the panoramic views.
Italy is home to some of the world’s greatest artwork and architecture. You will spend two nights in Avellino, which is in the southern region of Campania, for an introduction into the captivating towns in the district of Irpinia. You can also traverse the halls and grand galleries of Caserta Palace, which is one of the largest royal complexes in the world. Three nights in Rome will be the perfect amount of time for you to explore the Roman port city of Ostia Antica, the ancient necropolis of Cerveteri, and the hilltop town of Orvieto.
Starting Price
$4,300 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 1266 reviews
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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We visited Madrid, Toledo, San Sebastián, Bayonne, Biarritz, Saint-Jean-de-Luz, Hondarribia, La Rioja, Barcelona, Montserrat, and the Penedes (Cava) region.
We loved our private guides, private wine tastings, and day trips outside of the big cities.
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We did a lot of research on tour groups and travel companies, and are so pleased we chose Zicasso and their specialized Italy team. They organized every detail of transportation, first-class hotels, and cut-the-line attraction visits with extremely knowledgeable local guides.
We ran into some minor interruptions due to protests and our team quickly navigated around them with their in-country specialists. We felt we saw the best of each location, with additional free time to explore other local things like food, shopping, etc. These folks know their stuff and we will look to use them in the future.
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We loved our trip to Spain and Portugal! We enjoyed each of our private tours with our tour guides in the various cities we experienced. They went above and beyond to share their knowledge of the planned sites, plus they added in individual unique sites and information along our walking route.
Zicasso’s tour company took all of our requested activities, venues, and interests to customize a trip that fit us well. They were in communication with us during our trip when a planned site was not available due to construction. Our tour guide provided us with other possible replacement options and let us choose what was of interest to us rather than them making the decision.
We tremendously enjoyed all of the cities, Madrid, Toledo, Granada, and Seville in Spain and Lisbon and Porto in Portugal. Our trip went smoothly and the activities were scheduled at a good pace for us! An extra bonus for us was seeing King Felipe VI by being in the right place at the right time near the opera house in Madrid while we were on our walking tour. We highly recommend Zicasso and the tour company.
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Zicasso’s tour company provided a well-organized trip, with every arrival and transfer smoothly arranged and plans well outlined. The trip was arranged to meet all our requests and their local guides were excellent. Our only complaint would be that when we decreased our hotels slightly for cost control, one of the three hotels did not meet our expectations as it seemed a bit heavily worn/lower tier compared to the others, and was located on the busiest street in Madrid, which was a higher stress location.
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We loved our itinerary! We gave the locations we wanted to visit to Zicasso’s tour operator and they fit everything in. They were with us every step of the way and listened to feedback about any adjustments, and stayed within budget.
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