Historical & Cultural Exploration of Milan Tour

What to expect on this itinerary
The history and culture of Milan can be felt around every corner of the city. Explore Milan’s rich history and intriguing culture during an immersive, 7-day vacation. From ancient Basilicas to world-renowned paintings, discover some of the best attractions and landmarks that Milan has to offer. Step back in time as you tour buildings that date back hundreds of years, and experience the culture of Milan through art and opera. Take a day trip to the nearby city of Bergamo to see another historical and ancient destination firsthand. Milan’s fascinating history and culture are yours to uncover and enjoy during this amazing, one-week adventure.
Customizable Itinerary
Milan – Arrive in Milan and Tour of Brera Art Gallery
The Italian city of Milan is rich in history and culture, and the modern business and fashion world blends with the historical landmarks of the city. You will arrive at Malpensa Airport to begin your immersive, 7-day vacation that will have you exploring Milan’s history and culture firsthand. A private transfer will greet you upon your arrival at the airport and lead you to your centrally located and luxurious hotel. Soon, the first of many expert guides will lead your first private tour. This afternoon’s destination will be the Pinacoteca di Brera or Brera Art Gallery. Part of the Brera Academy of Fine Arts, the Gallery is a treasure trove of magnificent paintings that will have you marveling at works by Bellini, Tintoretto, and more master artists as you are led around the museum. Raphael’s Marriage of the Virgin will be particularly striking; it is an oil painting that depicts the marriage of Mary and Saint Joseph and was completed in 1504. Once the tour concludes, the fresh air of the nearby Brera Botanical Garden will be an ideal place to spend the remainder of the day.
What's Included:
Milan – Tour Sforza Castle and Monumental Cemetery
Milan – Visit Milan Cathedral and La Scala Opera House
Milan – Day Trip to Bergamo
Milan – Explore More of Milan’s Historical Churches
Milan – Discover Merchants Square and Galleria Vittorio Emanuele II
Milan – Depart for Home
Trip Highlights
- Delight in a visit to the Brera Art Gallery to see world-renowned paintings, including Raphael’s Marriage of the Virgin
- Marvel at the ancient Sforza Castle during a tour, where you will see the Rondanini Pietà, which is Michelangelo’s last sculpture
- Witness amazing monuments and gorgeous statues during a guided tour of Monumental Cemetery that is recognized as the city’s open-air museum
- Bask in unparalleled views of Milan when you ascend to the rooftop of the Milan Cathedral during an intriguing tour
- Experience an unforgettable live performance at the famous La Scala Opera House
- Immerse yourself in Bergamo’s 16th-century walls, which is a UNESCO World Heritage Site, during a day trip to the city
- Venture through the Church of Santa Maria delle Grazie to view Leonardo da Vinci’s stunning Last Supper painting
- Explore the history and vibrant culture of Italy’s oldest shopping mall, Galleria Vittorio Emanuele II, during an exciting visit
Detailed Description
This discovery-tour of Milan’s history and culture will take you to ancient buildings, historical churches, and wonderful museums. You will land at Milan’s Malpensa Airport to begin this exciting journey. After becoming acquainted with your luxurious hotel, you will enjoy a private tour of the Brera Art Gallery, where you will be able to witness timeless paintings by great artists such as Raphael and Tintoretto. The following day, you will continue your exploration of Milan’s history with visits to Sforza Castle and Monumental Cemetery. The ancient Sforza Castle is home to fascinating museums, and one of them is home to Michelangelo’s last sculpture, which you will be able to see during your exclusive tour. Monumental Cemetery is considered more of an outdoor museum than a cemetery, and you will be in awe of its gorgeous statues and monuments.
An Italian pastry and freshly brewed espresso will be the perfect way to begin your next day. After breakfast, you will venture to the Milan Cathedral for a private tour. The architecture and details of the Cathedral will be stunning, and you will appreciate the stained-glass windows and works of art. You will have the unique opportunity to view the city from a unique viewpoint when you ascend to the rooftop of the Cathedral and enjoy the unparalleled views. Later in the day, your tour will continue to the legendary La Scala Opera House. After you take in the beautiful decor of the main auditorium and antique instruments of the museum on a guided tour, you will immerse in the culture of Milan with a live opera performance. The amazing show will be memorable and a wonderful way to culminate your day.
The following day, you will indulge in an excursion to the nearby city of Bergamo. Here, you can view ancient buildings, the 12th-century Basilica of Santa Maria Maggiore, and the spectacular Colleoni Chapel during your tour of this medieval city. After the day’s exciting trip, you will return to Milan by the evening. Another wonderful look into Milan’s history will await you on day five as you explore more of the city’s magnificent churches on guided tours of the Church of Santa Maria delle Grazie, the Basilica of Sant’Ambrogio, and San Maurizio al Monastero Maggiore. Colorful mosaics, detailed frescoes, and well-preserved paintings will be found at every one of these special destinations, and the opportunity to see Leonardo da Vinci’s painting of the Last Supper will make the visit to the Church of Santa Maria delle Grazie especially unforgettable.
As the sun rises over Milan on the morning of day six, you can savor a tasty breakfast before your tour for the day begins with a visit to Piazza Mercanti. The delightful square is filled with historic buildings, and it will transport you back in time as you discover ancient buildings that used to house the city’s courts and notary. You will also have the unique chance to see a 17th-century school. In the afternoon, you will transfer to Galleria Vittorio Emanuele II, which is Italy’s oldest shopping mall. Here, you will be able to immerse yourself the culture of the city as you journey around the many high-end shops and boutiques. A stop in one of the mall’s delicious cafes or restaurants will be the ideal way to end your visit.
Finally, on the morning of your last day in Milan, you can delight in one more walk around the city before a private transfer leads you to Malpensa Airport for your return flight home. You will have experienced the best of Milan’s history and culture during your amazing weeklong vacation. Consider learning more about our travelers’ favorite Italy travel experiences by reading their Italy travel reviews.
Starting Price
$3,200 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 6172 reviews
Our trip to Italy was absolutely amazing. Zicasso’s travel company provided exceptional service and attention to detail. We had never used a travel company for arrangements prior to this trip and we are so glad we did. It made the trip stress-free and truly over-the-top.
Our favorite time on the trip was at a location recommended by our travel agent in a very small area called Ciociaria. We loved this location and our resort in Ciociaria. The staff was incredible and we felt so relaxed.
I have been telling all my family and friends about the travel company’s services and that I will use them for future trips. I am so thankful to Zicasso for connecting me to an incredible experience with our travel company.
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This was our first time using a travel agency for a trip like this and Zicasso’s travel company completely exceeded our expectations. Traveling internationally with pre-teen children can be stressful, but from the very beginning, this travel company removed every bit of that anxiety. Every detail was thoughtfully planned, clearly communicated, and flawlessly executed.
From airport transfers to hotels, tours, trains, guides, and daily logistics, everything worked seamlessly. We never once felt lost, rushed, or unsure of what was next. Instead of worrying about schedules or navigating a foreign country, we were able to fully focus on our family and enjoy the experience. That peace of mind alone was invaluable.
What really stood out was how well the trip was tailored to our family. The pacing was perfect, the experiences were engaging for adults and kids, and every guide we worked with was knowledgeable, friendly, and professional. It truly felt like a curated, high-quality experience rather than a generic itinerary.
We came home with incredible memories and zero travel stress, something I didn’t think was possible with kids that age. This travel company was phenomenal and we would absolutely use them again, and recommend them without hesitation to anyone considering international travel, especially families.
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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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Thank you to Zicasso’s travel specialist and her amazing staff. The itinerary was fabulous. It was filled with food, wine, and highlights of the most important tourist places. Her guidance throughout the year-plus planning was the right amount of checking in and waiting. Thank you for the nudges to have reservations for all the holiday days. Things seemed to be pretty open overall, but it was nice not to worry.
All the restaurants set up for us were wonderful. The app was terrific to keep track of what we were doing when. All the drivers were very friendly, professional, and punctual.
Thank you for making our 35th wedding anniversary trip (December 22 2024 to January 6 2025) a most memorable one. We hope to return to Italy to enjoy the southern area and maybe some of the beaches and islands.
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We had an excellent itinerary and we really liked the accommodations provided, and their locations within walking distance of our must-see sites.
Excellent tour guides, drivers, and transportation were provided!
The Zicasso travel expert's recommended restaurants were also great and the guidelines were helpful!
My husband and I saw and enjoyed what we needed to see and experience!
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It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.
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