Couples Getaway to Italy’s Fashion Capital

Milan, Italy

What to expect on this itinerary

Milan is one of Italy’s most elegant cities. Typically known for fashion and business, Milan will not do anything short of impressing during your week in this luxurious city. Enjoy a 7-day vacation in this fabulous city that is specifically designed for couples. Romantic boat rides and candlelit dinners await you, along with artistic and historical wonders like Leonardo da Vinci’s Last Supper and La Scala Opera House. An excursion to idyllic Bellagio rounds out this memorable and unique couple’s trip through Milan. This 7-day, romantic excursion through Milan will have you reminiscing about this trip for the rest of your life.

Countries Visited

Italy

Places Visited

Milan, Bellagio

Suggested Duration

7 Days

Customizable Itinerary

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Day 1

Milan – Arrive in Milan and Evening Canal Cruise

The first feelings of amore, or love, will set in as you arrive in Italy to begin your wonderful couple’s vacation in one of its leading cities, Milan. A private transfer will greet you at Malpensa Airport and bring you to the luxurious hotel that will be located in the heart of the city. You will have time to get acquainted with the hotel and your luxurious room before heading out on an exclusive evening sightseeing cruise along one of Milan’s canals. The city’s interconnecting canals date back hundreds of years, and you will set sail on a private boat tour of the oldest canal: the Naviglio Grande. The serene waters and quaint buildings that you pass will certainly set the perfect romantic atmosphere. As you glide around the winding waterways, you will learn about the history of the canals and bask in all the sights and sounds from your unique perspective. When the cruise concludes, you can share a sweet gelatoor Italian ice cream for two from one of the many gelateriasin the area before returning to the hotel.

What's Included:

Transfer
Accommodation
Tour
Day 2

Milan – Tour of Milan Cathedral and La Scala Opera House with Show

Day 3

Milan – Visit Galleria Vittorio Emanuele II and Sforza Castle

Day 4

Bellagio – Sights of Lake Como with Boat Ride and Dinner

Day 5

Milan – View Leonardo da Vinci's Last Supper and Wine Tasting

Day 6

Milan – Visit Brera Art Gallery and Botanical Garden and Dinner on Tram Restaurant

Day 7

Milan – Depart for Home

Trip Highlights

  • Bask in an evening canal cruise around Milan
  • Witness an unforgettable show at the famous La Scala Opera House
  • Shop in high-end boutiques at Galleria Vittorio Emanuele II mall
  • Marvel at Leonardo da Vinci’s Last Supperpainting during a visit to the UNESCO World Heritage Site Church of Santa Maria delle Grazie
  • Enjoy an excursion to the fabulous village of Bellagio
  • Venture to gorgeous Lake Como on a private boat
  • Indulge in an exclusive tram restaurant in the heart of Milan

Detailed Description

An immersive and romantic 7-day couple’s vacation in Milan will begin when you land at Malpensa Airport. After checking into the centrally located and fabulous hotel, you will have some free time before setting out on an evening sightseeing cruise along Milan’s Naviglio Grande canal. Take in the sights of the old buildings and learn some of the history that relates to the canals as you travel in a private boat. Day two of the vacation will begin with a trip to Milan’s Cathedral. The impressive church will amaze you with its detailed statues, and you will enjoy the vast views of the city from the cathedral’s rooftop. In the afternoon, the tour will continue to the world-famous La Scala Opera House. Here, you will witness the main auditorium and nearby museum before viewing a special opera performance in the evening. The legendary building and romantic music will be a perfect end to the day.

A combination of shopping and history highlight day three, which will feature exciting visits to Galleria Vittorio Emanuele II and Sforza Castle. During the trip to Galleria Vittorio Emanuele II, which is one of the world oldest shopping malls, you will discover some of the best of Italian fashion and have the opportunity to shop at high-end boutiques such as Gucci and Prada. After lunch, head to the ancient Sforza Castle. This grand castle is home to various museums and exploring them will be a great way to dive deeper into Milan’s history and culture. You will then have free time in the park, Parco Sempione, which is located outside the castle, to spend at your leisure. The beautiful green grass and pretty flowers will be the ideal way to balance your day. On the morning of day four, you will depart Milan for a one-night excursion to the renowned village of Bellagio. Your private transfer will first stop in the city of Como where you will go a tour of its main attractions before embarking on a private boat ride around the gorgeous Lake Como. After taking in all the spectacular sights of the lake, you will arrive in the waterfront village of Bellagio. The village is highly sought after for its ideal location that overlooks the lake and its luxurious villas, and you will spend one night in a lavish hotel that is located on the water where you will also have a romantic dinner for two.

Feeling totally relaxed and content, you will return to Milan via private transfer on the morning of day five and begin a tour of the Church of Santa Maria delle Grazie. The ancient church will be filled with sights to see, and the highlight of the visit will be having the opportunity to view Leonardo da Vinci’s masterpiece: the Last Supper. Later today, you will head to a local wine bar for a private wine tasting. Here, you will have the chance to sample various delicious wines as you learn about the winemaking process and discover your favorite, Italian blend. Day six of your vacation will feature a visit to the Brera Art Gallery and Brera Botanical Gardens. The massive gallery will fascinate you with its hundreds of works of art by master artists such as Raphael and Bellini. The botanical gardens will also be extraordinarily scenic and peaceful. For dinner, you will have the exclusive chance to dine aboard one of Milan’s most prestigious restaurants. This will be a very unique experience as you will be served the utmost romantic and delicious meal as you ride through the breathtaking city. This sought-after experience will be the perfect way to spend your last night in Milan. On the morning of day seven, your private transfer will lead you to Malpensa Airport for the return flight home. This couple’s trip to the best of Milan’s attractions and most romantic locations will be remembered forever.

Starting Price

$2,600 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.

4.9

Verified Traveler Reviews

Based on 1156 reviews

Italy Tour Review: Venice, Florence, Tuscany, Lake Como, Milan, Truffle Hunting, Wine Tasting, Cooking Class, Boat Ride, 2-Week Trip

Our trip to Venice, Florence, Tuscany, Lake Como, and Milan was exceptionally well planned and executed by Zicasso's tour operator.

The transportation from one location to another was efficient, even when challenged by the high tides in Venice. Overall, the hotels selected were very good. The one in Montalcino was exceptional. Every guide was knowledgeable and professional. We appreciated their willingness to be flexible. Our driver for the ride to Como and back to Milan was personable and exceptional as well.

We really enjoyed the truffle hunting experience, the first wine tasting in Montepulciano, where we met the entire charming family, the cooking class in Bellagio with a chef who treated us like family, and the boat rides on Lake Como and to the islands in the lagoon of Venice. All of the dinner reservations were spot-on and when there was a slight misunderstanding regarding our wine tasting in Bellagio, where the staff at the hotel in Bellagio had no idea what had been arranged by our agency, this was quickly resolved by our guide through texts and emails with the agency.

The only aspect of the trip that could have been improved was day eight, when our activities, travel time, and late dinner reservation resulted in a late-night drive back to the villa. The hotel in Milan was difficult to find at first due to its location not being visible from the street. Once we found it and settled in, it was in an excellent location for our sightseeing. The gifts of sparkling wine at two of our stops was thoughtful and appreciated.

We thank our agent and the staff at the agency for a wonderful trip and would not hesitate to recommend the firm to our friends and family.

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Italy Travel Review: Rome, Florence, Naples, Ischia, Vatican Museums, Skywalk, Wine Tasting, Olive Oil Sampling, 2 Weeks

Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.

The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.

In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.

Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.

At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.

Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.

We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.

We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.

We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.

I can’t wait to use the travel company again next year.

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Italy Trip Review: Venice, Stresa, Lake Como, Local Cuisine, Private Tour, History, Culture, 8 Nights

This was our first experience with Zicasso’s travel company and, thus, with our travel designer. We were a bit concerned because our trip with a travel company back in 2001 had a few bumps along the road. However, once the private driver arrived and met us after exiting our cruise, all the worries and concerns began to vanish.

Our travel designer created an amazing itinerary and every step of the way was seamless. She took care of every single detail and provided us with all the instructions (guidance, maps, contact information, and all train tickets first class) we needed. All I can say is, she surpassed our expectations. The tours she booked for us showed they were carefully crafted based on our interests and all the guides were magnificent.

She allowed time for us to recover from the train rides; the hotels were perfectly situated, all amazing; and the private transfers were timely and extremely pleasant. She sent drawings of where our drivers would meet us. All I can keep stating is she is amazing!

We boarded the first private transfer at the approved area and our driver drove us to the Bologna train station. When we arrived in Venice, there was a young man waiting for us to take us to our private water taxi, which water taxied us right in front of our hotel. The hotel attendant assisted us with the luggage and checked us in.

She booked us at our hotel in Castello in Venice for three nights. The hotel was on the main street, but was away from the craziness of St. Mark’s Square. We had our first small-group, skip-the-line-tour on day two, with a guide from a local partner who was fantastic. He was witty and knowledgeable. Later we found out he was a professor—no wonder his knowledge of dates and history was so extensive. On our third day we met with a guide, again from the local partner, similar to the day before: small tour, skip the line. Our guide was also fantastic.

After our stay in Venice, we went to Stresa. Again, pick-up from our hotel with the water taxi was timely and the drop-off at the train station was smooth. Once we arrived in Milan train station, there was a driver waiting for us, who took us directly to our hotel. The location was magnificent and we could walk easily along the main street, right in front of the hotel.

The next day we met our guide, who picked us up at our hotel and took us on a full-day excursion to the three islands. He was extremely knowledgeable and worked with us at our pace. His incredible knowledge of history and his kindness won us over. Our travel designer pre-arranged lunch at one of the islands, which was outstanding.

Our last visit was to Como. I was a bit disappointed when we arrived at Como. The main area, where you see the charter boats, seemed small based on my expectations. She arranged a private tour that took us to two islands. That trip showed us the Como I had anticipated. We ended up in Bellagio where we had a late lunch at the restaurant at the tip of Bellagio and the boat picked us up and took us back to the main island. It was beyond words.

If you are visiting Italy, reach out to our travel designer; she will surely exceed your expectations.

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Switzerland, Italy Trip Review: Luzern, Geneva, Murren, Grindelwald, Lake Como, Bellagio, Gondolas, Cable Car, E-Bike Tour, Kayaking, Chocolate Experience, 14-Day Tour

We had a wonderful trip to Switzerland and the Lake Como area. Zicasso's tour agency curated the perfect itinerary, combining some relaxing days with some active days. The e-bike tour through the Lavaux vineyards and kayaking in Bellagio were definite highlights. They chose beautiful hotels in perfect locations for easy access to the metro and local sights. Having them take care of all of our tickets and train passes ahead of time made for a stress-free trip!

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Italy Vacation Review: Venice, Florence, Rome, Sorrento, Murano, Burano, Pisa, Vatican, Colosseum, Pompeii, Capri, Private Tours, Cooking Class, 10 Nights

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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Italy Marriage Proposal Trip Review: Milan, Menaggio, Lake Como, Rome, Amalfi Coast, Naples, 'The Last Supper', Walking Tour, Boat Tour, 9 Nights

I booked this trip with the intention of proposing to my long-time girlfriend. From the get-go, my travel agent helped me plan every day with a tailor-made itinerary. She helped ease my anxieties and make my proposal very special.

Our trip to Italy involved flying into Milan and spending two nights there. We were able to see The Last Supper on a walking tour of the city. From Milan, we took a taxi to Menaggio, alongside Lake Como. We really loved Menaggio as it was the perfect quiet getaway in one of the most beautiful places I have ever visited. From Lake Como, we continued down to Rome and the Amalfi Coast and Naples. My fiance and I really enjoyed our trip and we hope to be able to return someday. Many thanks to our Zicasso agent and the team at her company for making it happen!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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