A High-End European Vacation: Amsterdam, Florence, Cinque Terre, Portofino & Milan

I live in the Chicago area and we were able to reserve a nonstop flight on United Airlines from Chicago O’Hare to Amsterdam Schiphol. We have never visited Amsterdam, so we wanted a few days to explore the city before we moved on to the bulk of our vacation in Italy. After a seamless flight, we were picked up at the airport by a driver I booked ahead of time. The driver met us in the reception area and we were quickly on our way in a comfortable Mercedes sedan.

Amsterdam

I booked our two-night stay at the Rosewood Amsterdam and I honestly cannot imagine staying anywhere else if I travel to Amsterdam again. From the moment we arrived, we were treated warmly and professionally by every staff member we encountered.

The hotel dates back to the 17th century and was once the Palace of Justice. The bellman told us that some of the original jail cells are now used to store wine. After a massive renovation, the hotel opened in May of 2025 and it truly is a work of art. The rooms are comfortable and modern with all the technology and lighting that you would expect from a Rosewood but with a hint of the history from the building’s origins. The owners have provided a number of art pieces from their own collections and one of the employees gave us a quick tour, pointing out some of the more unique art pieces found throughout the hotel.

Make time for a dip in the indoor pool and hot tub. It was so relaxing after a long flight and a day of sightseeing. We were the only people in the pool area in the evening and it was a great experience. Thanks to our Fora Perks, we had a $100 hotel credit, a personalized welcome with a fruit and cheese platter in the room, and daily breakfast, which was excellent.

Rosewood Amsterdam welcome

We only had two days in Amsterdam, so, shortly after arriving at our hotel, we set out to explore the city. Rosewood is located just south of the city center and walkable to anywhere we wanted to visit. Our first afternoon, we were fortunate enough to have tickets to the Anne Frank House. Securing these tickets is very challenging, so it's essential to make your booking well ahead of time. I booked them through a third party and crossed my fingers that they would work, and fortunately they did. The museum is incredibly well done, and we were both amazed by the entire experience.

Right outside the Anne Frank House, there are boats that take people on a one-hour canal tour. We were able to book a boat on the spot and had a nice and informative tour of the city from a canal view. Keep in mind that some of the boats also have full bars—we chose wisely, so we had a few glasses of wine while we sailed. Our boat was part of the Flagship fleet and we would highly recommend it. Afterwards, we grabbed an early dinner and headed back to the hotel for the evening, since we had not yet slept since arriving in Amsterdam.

The next morning, after a great breakfast, we decided to walk toward the museum complex, which is about 10 minutes from the Rosewood. There are several wonderful museums, including the Van Gogh and the Rijksmuseum, but we decided to try the Moco (short for modern contemporary) Museum. We both like contemporary art and we enjoyed seeing the works of artists like Banksy, Keith Haring, and Andy Warhol. It’s not a huge museum so it doesn’t feel overwhelming, but it can be crowded.

From the Moco, we moved on to our primary destination for the day—the Heineken Brewery. Our son visited the brewery during a semester abroad and told us we absolutely needed to go, and he was right. It was one of our Amsterdam highlights. Even if you are not into Heineken beer (or beer at all) it is just a fun experience. Our ticket included an extra rooftop experience, which should not be missed. Heineken has done a wonderful job making a fun, immersive, and informative tour.

We had three goals for our final evening in Amsterdam: Holland fries from Mannekinpis, stroopwafels from Stroopperie, and a visit to the red light district. After getting our fill of fries and a stroopwafel (which were both excellent) we wandered over toward the red light district. Even though we had a general idea of what to expect, it still is a bit shocking to see how many windows there are and how many people descend on that area to “people watch.” We did not stay long because it was getting increasingly crowded so we made our way back to the hotel for the rest of the evening. The following morning, we had our final breakfast in Amsterdam before heading to the airport for our flight to Florence.

Amsterdam Canal

Florence

After a two-hour flight to Florence and a quick exit from the airport, we took the T2 Tram to get us into central Florence. We had read that the tram can often be the fastest way to the city, and 20 minutes later, we were downtown.

From there, we walked to the Hotel Il Tornabuoni, which was our home for the next three days. Our Fora Perks included a $100 hotel credit, a welcome bottle of wine and a small fruit plate in the room, and daily breakfast. The Il Tornabuoni is a Hyatt property right in the city center and is in a great location, walkable to anywhere in the city. The hotel itself is charming and unique. There are a number of steps to get to and from rooms so if you have mobility issues, this may not be the best hotel for you. We really enjoyed the hotel’s rooftop bar, which had live music one evening.

One of our primary reasons for visiting Florence was to visit the wine windows. If you are not familiar with wine windows, they are small windows often attached to bars or wine shops where you can buy a glass of wine to drink on the street. Wine windows have been in Florence and the surrounding area since the 1500s and allowed wealthy families to sell surplus wine directly from their homes while avoiding taxes. They also became a method to sell wine and other goods during the plague outbreaks with minimal contact.

Our goal was simple: Visit as many wine windows as possible. While there are hundreds of wine windows in Florence, only a small number are still being used today. We found a map with the “active” windows and drank wine at eight different windows. The following day, we happened across a ninth window that was not on the map, so there may be even more out there hiding! The wine windows were a lot of fun and we really enjoyed walking around the city seeing areas we never would have visited if we were not looking for the windows.

Florence wine window

The following afternoon, we took a pizza and gelato (and wine!) cooking class, which was an absolute highlight of our trip. The chef had a great personality and we learned a lot about the cooking process for a traditional Italian pizza. The pizzas were amazing!

A popular Florence activity is to watch the sunset from Piazzale Michelangelo. This is on the south side of the Arno River and is a bit of a climb to the top of a hill, but you are rewarded with unbelievable views of the city. It will also seem like the entire city is on the hilltop with you, so if you want a place to sit, you may need to get there an hour or more before sunset. There are places to get food (and wine) and some carts selling souvenirs.

One other thing my wife and I really wanted to do was to visit All’Antico Vinaio. We went to one of their locations in the Broadway area of New York City but really wanted to visit it in Florence. When we got near the shop, we saw a massive line and were tempted to turn around, but someone told us it moves fast, and they were correct. Less than 10 minutes later, we were sharing an amazing sandwich.

While I am on the subject of food, we also had a great meal at one of the restaurants around the Piazza della Signoria. We just walked around and looked at menus until we saw one we wanted to try.

We packed a lot into three days in Florence and left wanting more time. Florence is definitely a city I would visit again and I hope to in the future.

Florence Duomo

Cinque Terre

We were now moving on to our next destination, Cinque Terre. Cinque Terre is a Unesco World Heritage Site west of Florence on the Ligurian Sea. To get to the area, we walked from our hotel to the Florence Central train station and caught a high-speed train to Pisa. There, we transferred and took a train to Monterosso al Mare, one of the five villages that make up Cinque Terre. The trip took about two and a half hours in total, and the journey was very relaxing.

When we arrived in Monterosso, we walked from the train station to our hotel—the Hotel Porto Roca. Hotel Porto Roca is the most luxurious hotel in Cinque Terre and is the only four-star hotel in the five villages. For other upscale options, you can stay in Porto Venere or La Spezia, but we were very happy to be right in Monterosso. After checking into our hotel, we wandered into Monterosso and had a nice dinner along the waterfront.

We only had two nights in Monterosso, and our primary goal was to do the very popular walk between the villages. The next morning, we had breakfast and set out on our hiking adventure. One nice feature about the Hotel Porto Roca is that it is directly on the path to the next village and there is a gate right on the property to access the path. Monterosso is the northernmost town in Cinque Terre, so we were going to be walking south to the other villages.

Our first stop was Vernazza, a picturesque town about a two-hour walk from Monterosso. I will say the hike was more strenuous than I expected, but we made it with no issues. In Vernazza, we had a bite to eat in the harbor before tackling our next hike, which took us to Corniglia. This hike was every bit as challenging as our first leg and again took about two hours. Once we arrived in Corniglia, we discovered that the trail to Manarola was closed and the alternate trail was a very difficult four-hour walk. We decided to instead take the train that runs between all the villages and quickly made it to Manarola.

Vernazza-Cinque Terre

Our final hike took us from Manarola to Riomaggiore on the Via dell Amore (Path of Love). This is a famous and easy pathway between the two villages and, if you are visiting Cinque Terre, it is highly recommended. The views are amazing when you walk between the villages, but there are numerous stairs and elevation changes and it is not an easy hike. We also had perfect weather in October, so if you are there in the summer, expect larger crowds and bring water.

With our goal of visiting all five villages complete, we caught a train back to Monterosso and headed into town to find a good place to eat. We were both very tired after our strenuous day, so we made our way back to our hotel and fell asleep quickly. The next morning, we checked out after a nice breakfast and made our way back to the train station for our trip to Portofino.

Portofino

To travel from Monterosso to Portofino, we took a train from Monterosso station to Santa Margherita Ligure. From there, we walked to the harbor and caught a ferry that brought us right to Portofino. I think arriving by ferry into Portofino is the best way to visit the city. It is one of the most beautiful towns in Italy, and arriving by boat is a great way to take it in.

Our home for the evening was the Splendido Mare, steps from the boat dock and right in the action on the harbor. We booked a Junior Suite Sea View with Balcony, and our Fora Perks included breakfast and a 90 Euro resort credit. Splendido Mare is a Belmond property and it has a sister hotel in Portofino in the hills above town, simply called Splendido. The Splendido is more famous (and certainly more expensive) and although I never visited the property, I can’t imagine a better location than the Splendido Mare. We loved the property, and we had a gorgeous room overlooking the harbor with a small patio where we shared a glass of wine from the bottle that was provided compliments of the hotel. All the restaurants and shops of Portofino are just outside the front door of the hotel.

Portofino is a small town that can be explored in a few hours. It is also an expensive town, so if you are on a budget, it would be easy to stay in Santa Margherita Ligure and just take a ferry into Portofino for the day. Keep in mind that the ferries can sell out and even though we were there in October, the boat was pretty full. During our visit, Portofino did not seem overly crowded. I have heard it can be incredibly busy during the summer months.

An absolute must-do while visiting Portofino is to walk to Castello Brown. You may have seen the Instagram videos of people opening the shutters and seeing a panoramic view of Portofino. It is a bit of a climb to the castle, but the views are absolutely worth the effort.

After a peaceful night in our extremely comfortable bed, we had an excellent breakfast on the restaurant patio before saying goodbye to Portofino. For our return trip, the ferry timing did not work well with our train schedule. We once again arranged for a private driver to take us on the 30-minute drive to the main train station in Rapallo. In Rapallo, we caught the train for the two-hour journey to Milan.

Portofino view from Castello Brown

Milan

Our train arrived at the Central Milan train station and we caught an Uber for the short drive to our hotel, the Park Hyatt Milan. The Park Hyatt is a beautiful hotel right in the center of town and steps from the Milan Duomo. Our Fora Perks included free breakfast, a $100 resort credit, a welcome amenity (chocolates and a bottle of wine), and early check-in and late check-out. The room was perfect, and if in Milan again, I would strongly consider staying here.

We only had one night in Milan, so after checking in, we immediately started exploring. Our first stop was the Galleria Vittorio Emanuele II, which is a glamourous shopping mall across the street from the hotel. If you watched the 2026 Winter Olympics, you may have caught interviews and other shots from this area.

We had one primary goal during our visit to Milan—visiting the refectory of the Convent of Santa Maria dell Grazie. This happens to be the place where Leonardo DaVinci painted the Last Supper on a wall in the dining hall. This may be one of the most difficult museum tickets in Europe to acquire, so plan accordingly. Only a small number of people are allowed in at a time and visits are short, but it is well worth the time and effort. The museum is a pleasant 20-minute walk from the Duomo, so if the weather is cooperating, it is a nice stroll. Later that evening, we dined at a restaurant overlooking the Duomo and then headed back to our luxurious suite to pack up all our items we bought during our time in Europe.

Last Supper in Milan

The following morning, we had our final breakfast in Europe and took our last private ride to the Milan-Malpensa airport. Keep in mind the airport is pretty far from downtown—the trip can take an hour, especially during busy times. After a pleasant drive with a pleasant and informative driver, we arrived at the airport. We again had a nonstop flight back to Chicago on United Airlines.

Milan Duomo

Final thoughts

My wife and I like to differentiate between trips and vacations based on how strenuous they are, the number of destinations, the things we do, etc. I will say we both love to do stress-free vacations to places like Cabo, the Caribbean, and other warm-weather or beach destinations, but there are times when we want to do more adventurous trips. We would absolutely both view this as a trip. We averaged 20,000 steps per day during our 10 days in Europe. Keep in mind that you could easily do a similar itinerary at a more leisurely pace and use other transportation options instead of primarily walking, but we both love to walk, and I do think this is the best way to really get a feel for a city.

We had a wonderful time on this journey, but if I could return to only one destination, Florence would be my choice. Florence is really a magical place, and we both felt we could have spent more time there. This was our third visit to Florence, but it will not be our last.

I also want to acknowledge the properties we visited. We planned this as a high-end vacation, and the hotels we chose did not disappoint. We loved the luxury and location of the Rosewood Amsterdam and the Park Hyatt in Milan. We loved the quirkiness and central location of the Il Tornabuoni in Florence and the views from the Porto Roca in Monterosso and the Splendido Mare in Portofino.

Traveling in late September into early October allowed us to capitalize on slightly lower hotel rates and fewer crowds at all of our destinations. Florence still seemed very busy, but everything was manageable and we never had any long waits.

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