Italian Holiday: Milan, skiing in Madonna di Campiglio, Venice, Florence and Rome

Over the Christmas holiday we decided to take the boys to Italy. In order to maximize our time we flew  out on the evening on Christmas Day and arrived in Milan in the morning.
 
Our itinerary was a sampler tour of Italy, since the boys had never been there and we hadn’t been back in 20 years. We started in Milan, then headed north to the Dolomites for some skiing in Madonna di Campiglio. From there we drove to Venice, and after celebrating New Year’s Eve on the lagoon we took the (very early) morning train to Florence. And after falling in love with the city of Florence all over again, we took the train to Rome for the finale.
 
Here are my Four Main Takeaways for a Successful Trip to Italy:  

1.SKIING! Skiing in Europe is remarkably less expensive than skiing in the US, the skiing was great, and the slopeside food is fantastic. It you're there during the right season, is definitely worth the effort.

2.SCAVI TOUR! As soon as you know you have Rome on your itinerary, apply for the Scavi Tour at the Vatican. They only admit 200 people a day, and you literally get to descend through the layers of history under the Vatican.

3.GUIDED TOURS: Book guided tours for some key (busy) attractions when you can – not only do you get to skip the line (which is so important when you are trying to maximize your time) but you will get a wealth of information and detail from a docent – more that you will gleam from a tour book or a wall plaque.
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4.RESERVATIONS: While you are planning ahead, I also highly recommend making your key dinner reservations well before you depart. Thanks to technology, this is often easily done right through the restaurant’s web site. We didn’t encounter any issues while skiing because it was a smaller town and the food at our hotel was fantastic. But in the big cities of Venice, Florence, and Rome you will be competing with larges masses of other tourists (as well as locals) all trying to ensure a fabulous evening. It pays to do some research and plan ahead. I have listed some recommendations below.

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Day 1: Milan (12/26)
We did a great job of sleeping on the plane so we arrived rested and ready to take on the day.  I always recommend the overnight flights to Europe. As soon as the dinner service is ended, it is time for my turtle neck pillow and my eye shade and I am out. That way you arrive well-rested to conquer your first day of vacation.
 
We rented a car ahead of time in Milan for pickup at the airport. We didn’t need it to explore Milan since it is a very walkable city, but we needed it to get to Madonna di Campiglio for the skiing. The rental car center was attached to the airport in the parking deck. We quickly learned that none of the cars were large enough for the four of us, and our four large, hard sided bags. To be fair, even if we had used soft-sided luggage it still would not have all fit. (For the record - I was very proud of my efficient packing of ski clothes and my capsule collections and keeping it all to just one bag, but I digress.) We literally had to go back to the rental counter 3 times and get assigned multiple different cars and try the luggage Tetris game in each of them (and failing in each of them) before they were able to give us their version of a Jeep Cherokee, which held us and all of our bags - but only if the back seat folded down on one side, and the boys squished next to each other for the while ride. Not ideal. Not very comfortable, but we made it work. Because it was the absolutely the largest car they had.
 
Now we were  hungry and eager to see the sights.  It was not a long drive into the city, and we were able to park in a garage near all of the shopping.  to see some of the highlights. In fact, we were very close to the Instagram famous sandwich shop. Unfortunately the line itself was something to behold. We passed and headed on to the main plaza and the cathedral.
 
The Piazza del Duomo, and the pigeons, were both overwhelming. We walked all around the cathedral and enjoyed the architecture from all sides before heading inside. This also allowed us to get some freshly baked pretzels and some beverages from the holiday market along the way.
 
After taking in the enormity of the Duomo, we ventured to the roof for the indescribably breathtaking views. The combination of the architectural detail, the views of the city, and the complexity of the design combine to be something I could not have even imagined.
 
From there we had to experience the beauty of the Galleria Vittorio Emanuele II, and make a visit to its most famous resident – the bull mosaic.
 
After some gelato we wanted to explore more of the city, so we headed towards the
Sforzeco Castle. It was a lovely walk, and the castle was an amazing reward.  From there we headed into Sempione Park and visited the famous Mermaid bridge and the famous arch.
 
We were enjoying Milan so much that we left a bit later than we had initially intended, so it was dark for most of our drive to the Dolomites. Our destination was the Beverly Hotel in Pinzolo.  The drive was dark and twisty, and the roads were extremely narrow as we passed through various villages. It was nerve-wracking and mentally exhausting. But the hotel exceeded all of our expectations, and dinner was amazing.

Day 2: Madonna di Campiglio (12/27)
Our hotel was just a short walk from both the ski shop and the lift, which was incredibly convenient. I thought I was very clever to reserve our skiing gear ahead of time, but that didn’t seem to matter other than I had already paid.  It still took a little bit of time to get fitted, and then get the lift tickets. But we were on the mountain and skiing before lunchtime. We did take a midday break at the top for a snack, an Aperol Sprtiz and photos at the top of Doss del Sabion. We were incredibly lucky - the weather could not have been better.
 
We got back to our hotel and got cleaned up and went exploring into the town before dinner.  It was lovely, especially with all of the holiday lights and music. There was an alpine music performance, a small holiday market, a mulled wine booth (of course) and fondue! And then we returned to the hotel for another amazing dinner, and called it an early night so that could maximize our time on the slopes the next day.
 
Day 3: Madonna di Campilglio  (12/28)
For our second day of skiing, we drove a little farther up the mountain to an area called Campo Carlo Magno, that would have more green and blue runs for me and my younger son, and still have challenging runs for my husband and my older son. We met for lunch at the top of the mountain at Tre Ville. The vistas were amazing, and would could watch the snowboard park area while we ate.
 
At the end of the day, we exited the mountain near the slopeside igloo-looking disco that we had seen online. It looked very fun, very crowded, and definitely not kid-appropriate so we enjoyed the disco lights and music from afar.
 
After a very full day, we drove to the main town of Madonna di Campiglio to explore. The town was larger than we expected, and even had a main street area that was pedestrian only for many blocks. There was another holiday market, music, more mulled wine, and pictures with some sweet horses all dressed up for Christmas. We had a lovely time, but we decided to head back to the hotel to enjoy another wonderful meal for our last night in the Dolomites.

Day 4: 1st day in Venice  (12/29)
We got up early for our drive to Venice, knowing it would take about 3 hours. Driving the narrow country roads in the daylight was still nerve-wracking, but at least we could see how beautiful the towns were. We returned the rental car in the parking garage just over the bridge, then took a water taxi to the hotel. In addition to the fabulous reviews and its great location, I had selected the Hotel Dell’Opera because it has a water gate/entrance and I wanted the boys to
experience the city by water upon arrival.
 
After dropping off our things, we headed out to take in the sights. We started at St. Mark’s Square and got some lunch nearby. We unfortunately missed our timed tickets to the rooftop access tickets to T Fondaco dei Tedeschi, at Calle del Fontego Dei Tedeschi, Rialto Bridge. But if you can make that happen, I hear the views are great.
 
We had a 4pm meeting time with our guide for a sunset boat tour of Venice (The Secrets of the Grand Canal – Boat Tour from Viator). Our guide was a graduate student at the university, and was a wealth of knowledge about the city, the neighborhoods, and the history. The city was showing off between all of the gorgeous the buildings and their Christmas light displays. But the view of the large. Christmas tree at St. Mark’s from the water was just stunning.

Dinner that night was a casual affair at Rossopomodoro, near St. Mark’s at Calle Larga. I am sure that some people would say that it is a bit touristy, but the food was solid and plenty, and it was exactly what we needed after a day of over 22K steps. There are quite a few places just like it in the immediate vicinity – all of them are good. We ended up eating at couple of them.
 
Day 5: 2nd day in Venice (12/30)
I could go to art museums all day long, but I am realistic and acknowledge that I was traveling with teenaged boys who – while they love art museums as well – would easily become maxed out on art over the course of the next week if I didn’t mix it up a little. So I was excited to find the Doge’s Palace, Prison and Secret Passage Way tour from Get Your Guide. It was super cool, with exclusive access to the back passageways of the Palace, and we were able to visit the cell where Cassanova was held prisoner before escaping. And we got to walk over the infamous Bridge of Sighs.

After the morning tour we needed some energy, so we went in search of some cicchetti that I had seen from both Anthony Bourdain and Stanley Tucci. Cicchetti is essentially Venice's version of tapas. They are small, bite-sized appetizers that are typically enjoyed with a glass of wine  (ombra) in a bacari (bar). The word "cicchetti" comes from the Latin "ciccus," meaning "small amount," and they are a centuries-old tradition in the city. The cicchetti is usually displayed on the counters so that customers can pick the ones they want, then stand and chat while they eat and enjoy an ombra, or small glass of wine. (Note: In the Piazza San Marco, the wine vendors used to move their stands over the course of the day so that they would stay in the shade of the bell tower to keep the wine cool, which is how the term “ombra” came about for a small glass of wine.)
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I had identified two places to go to: All’Arco and Cantine del Vino. We ended up at All’ Arco, near the Rialto Bridge. It is definitely an institution, and therefore there is always a line. But the line moved fairly quickly, and the people watching was great. And the food was amazing so it is totally worth it.
From there we explored more of the neighborhoods in Venice, and the boys made the required stop at the official Venezia team store for some very cool jerseys. We had a great dinner that night at Al Gobbo.

​Day 6: 3rd day in Venice (NYE)
Today we took a morning water taxi to Murano, and thoroughly enjoyed the glassmaking experience at the Original Murano Glass OMG Factory and Showroom. Afterwards, we had an extremely memorable lunch at Ristorante La Fornace. The views back over the lagoon towards Venice were just beautiful, and the food was wonderful. I highly recommend making reservations ahead of time. 

After lunch we took the water taxi to the Peggy Guggenhim Collection museum.  I had bought our tickets ahead of time to ensure that we could visit, and since the museum is relatively small I would highly recommend doing the same. The collection is so unique and from such a pivot moment in modern art – it feels like you’re in a time capsule. I loved it.
 
From here we took the water taxi back to St. Mark’s Square.  I was feeling artsy and creative after the museum, so we headed to Harry’s Bar for some history and literary vibes before heading back to the hotel. Unfortunately I crashed when we got back to the hotel and spent NYE in bed with a fever and a horrible sinus infection, but the boys ventured out and enjoyed the fireworks at midnight. The photos were beautiful.

Day 7: travel to Florence
We had a very early train to Florence, and we did not want to risk missing it. The hotel helped us to make arrangements for an early morning private water taxi to pick us up at the hotel and take us to the Venice train station, which not surprisingly has some beautiful Murano murals at the entrance. Turns out that arriving to the hotel and departing the hotel by water was a very picturesque transition. The city was so quiet and empty at this early hour – it was a lovely way to say good-bye to Venice. We had pre-purchased our tickets for the trip to ensure that we had assigned seats on the train, as well as a table. We arrived in Florence at 9:20am so we still had a full day ahead to enjoy the city.
 
We checked into our gorgeous hotel, the Il Tornabuoni, which was located in an old palace in the heart of the historic old city. It was the most expensive hotel of the trip, but I wanted to ensure that the location would make it easy for the boys to explore on their own.
 
Our first stop was the Ponte Vecchio, then we explored the city and ended up at the historic Il Bottegone on the Piazza del Duomo for breakfast. From here we planned the rest of our day. This included a visit to the Cappelle Medicee (Medici chapels) and the Piazza della Signoria. I remember that last time I was at the Uffizi was shortly after I had taken Art History, and I still felt like it was just overwhelming. So we scheduled a small group tour of the Uffizi Gallery for the afternoon through Viator.  Our guide was fantastic – she clearly wanted to make and made sure that we did not miss any of the highlights of the collection.

Afterwards we indulged my quest to discover the famous Wine Windows (“buchette del vino”) of Florence. The history of the Wine Windows begins in the 1500s with Cosimo I de’Medici. He became the second and last Duke of Florence in 1537, and then the first Grand Duke of Tuscany in 1569, establishing absolute rule in the region. Some of the wealthy families in Florence were not happy about his rise to power, so to placate them he passed a law that allowed them to sell wine direct to consumers, if the wine had been produced at their country homes. In this way, those families avoided having to pay taxes. The wine windows continued to be relevant for hundreds of years. In the 1600s they provided a safe way to exchange wine, goods and currency during the plague.

The Wine Windows are now ubiquitous with the city, and in 2015 they even set up an organization to preserve their history. There are believed to be over 285 wine windows, with half of them clustered around the Old Town where the influential families like the Antinori, Frescobaldi, Rucellai and Verrazzano families that their homes and wine windows. The Santo Spirito neighborhood also has quite a few. Here are the ones we went to:
 
Babae, on Via Santo Spirito, 21R
Belle Donne, on Via della Belle Donne, 16R
Cantina dei Pucci, on Via de’ Pucci, 4A
DiVin Boccone, on Via delle Caldaie, 20
Il Latini on Via Dei Palchetti, 6R (we also ate at the restaurant and it was amazing!)
 
After visiting the wine window at Il Latini and wandering through the galleries across the street, we capped off the day there with an unforgettable dinner.

Day 8: Day 2 in Florence
We started the second day in Florence with the VIP David and Duomo Tour: Early Accademia Tour & Skip the Line Dome Climb with exclusive terrace access from City Experiences. I know the crowds in Italy have been historic this year, and I didn’t want to take any chances of getting to Florence and having the boys miss either of these highlights.
 
We spent the afternoon exploring the Ponte Vecchio, enjoying some more gelato, and doing a little shopping. We ended the day dashing between the lovely shops and the raindrops on the other side of the Arno, and grabbed a lovely dinner at Olivia Bistrot del Frantoio in front of the Palazzo Pitti (Pitti Palace) as we waited for the rain to dissipate.
 
This was our last night in Florence, so we left the boys to enjoy the plush robes and slippers and big TV in our room, and we headed to the lounge for drink. The hotel was truly spectacular, and I wish we had more time to enjoy it.

Day 9: Travel to Rome
The next morning was another early train for us (9:28am) which got us into Rome a few minutes before noon. Our first stop was the Hotel Abruzzi, located just to the edge of the plaza of the Pantheon (one of our absolutely favorite spots in Rome). Surprisingly, our room was ready so we were able to drop off our bags and settle in a little before heading out to have some lunch and explore.  The boys could not wait to see Rome!
 
We spent the afternoon exploring the ancient part of the city, the Spanish Steps, the Trevi fountain, and searching for the Roma soccer store, of course. I was excited to explore the Castillo de Sant’Angelo (also known as the Museum of Hadrian). I had never been there, so I was fascinated by the history of the ancient castle.  And since we arrived in the late afternoon, we left at twilight and the result were some remarkable photographs. We saw a lot, and covered over 25K steps.
 
Dinner that night was at Rimessa Roscioli, which came highly recommended from my cousin Nicole and her husband. They had lived in Italy for a while on sabbatical, and they had some phenomenal recommendations for us. This was definitely one of them. It surpassed all of our expectations and was another truly memorable meal. Oh - and we joined the Roscioli wine club. But I digress…
 
Many nights on this trip, the boys would want to get back to the hotel by 9pm to watch whatever professional European soccer game was on TV that night. At dinner the conversation turned to the fact that we would be getting back to the hotel just in time for the Roma soccer game to start. So I asked “Roma? As in Rome?” Because I had seen on the map that while we couldn’t walk to the stadium, it wasn’t that far away. We impulsively bought tickets online from the Italian version of StubHub before we even left the table at the restaurant. We hopped in an Uber and got there just a few minutes after the game started. And it was epic. It was everything you wanted a European soccer fan experience to be: Loud, yelling, flares in the fan zones, paddy wagons already parked outside as a deterrent to hooliganism. It was impulsive, a bit expensive, and absolutely worth it.

Day 10: Day 2 in Rome
 
We started our second day in Rome with the Colosseum Underground Tour with the Roman Forum and Palantine Hill from The Tour Guy. Rick Steves had highly recommended The Tour Guy, and you never go wrong when you listen to Rick. It was a three-hour tour that started in the Forum and on Palatine Hill, which was a great way to understand the history and layout of the ancient city. From here we met up with our small group at the Colosseum for a guided tour underneath the floor of the arena. There are only about 200 people a day are allowed in this area since it is an active archeological site. And it was fascinating to see first-hand how they could fill the arena with water to create sea battles, where they would keep the animals, and how the trap doors were designed.

We grabbed a quick breakfast of focaccia and coffee (tea for me) near the meeting point for the tour, know that that we needed some good carbo-loading for all of the walking that we would be doing. The tour started at 10:15, so we did not finish at the Colosseum until almost 1:30. We were starving by then, so we grabbed a lovely (very) late lunch nearby in the Monti neighborhood on our way to visit the Church of St.Lawrence and the Scala Sancta (Holy Steps). According to Catholic Church tradition, the Holy Stairs were the steps leading up to the praetorium of Pontius Pilate in Jerusalem on which Jesus Christ stepped on his way to trial during his Passion. The stairs reputedly were brought to Rome by Saint Helena in the 4th century

From here we timed our visit to the Church of San Pietro in Vincoli to see one of the most famous sculptures from Michaelangelo, the Moses of Pope Julius II’s tomb. We were there perfectly on time to see the rays of sunset come through the transept windows and brilliantly illuminate the sculpture.  It was amazing.

Day 11: Day 3 in Rome
Since I knew that the crowds would be heavy at the Vatican, especially at Christmas time, I had booked us a 9am Private Tour of St. Peter's, the Vatican, Vatican Museum and Sistine Chapel from The Tour Guy. We met our guide in front of the main entrance to Vatican City, and she was truly a wealth of information.
 
Before we left for our trip, we had learned about the Scavi tour that you can take underneath the Vatican and literally descend through the layers of ancient history under the Vatican.
You need to us this link to request a reservation. They only take 200 or so people through it each day and they separate the tours by language, so you’ll want to apply as soon as you plan your trip to Rome., They will email you with the date and time, and you pay them directly online. It was extremely affordable at about 7 Euros. The only issue for us was that no one under 15 is allowed on the tour, which meant that only Mike and Dylan could go. The appointment time they were given was 11am, so Liam and I had the last part of the tour by ourselves. We took good notes, and gave Mike and Dylan the same information once they were finished with the Scavi tour. 
 
The next stop was the Pantheon, right by our hotel.  But on the way there, we stopped nearby at the unique Elephant sculpture/obelisk in the Piazza della Minerva, just in front of the Basilica di Santa Maria Sopra Minerva. It turns out that this unique statue was designed by Bernini. The obelisk is from ancient Egypt and stood in the Temple of Iris and Serapis. It was brought to Rome by Diocletian (284-305 AD). In 1655 it was rediscovered in a garden of a Dominican monastery  and Bernini was commissioned to incorporate it into a statue. He drew inspiration from many sources but also from the fact that elephants were quite the rage at the time. So he proposed a a concept of a small but strong elephant that could bear the weight of the granite obelisk.
The story goes that a Dominican friar disapproved of the design, and convinced Pope Alexander VII to made Bernini make alternations to it. Bernini made the alterations, but got his revenge as well. He positioned the elephant so that it is forever mooning the Dominican monastery.

The boys had been desperate to go see the Largo di Torre Argentina, known for its abundant cat populations. So at this point in the trip we could not put it off any longer. The Largo di Torre Argentina is an archeological site in Rome that contains the remains of four Republican-era temples, part of the portico of Pompey, and the site of Julius Caesar’s murder. (!) After the excavation of the temple ruins in 1929, feral cats were drawn to the area, sheltered by the pillars and fed by the locals. Now the cat sanctuary is run by volunteers who care for the cats and provide food, shelter and medical care. We love to follow them on Instagram at @gattiditorreargentina. You’re welcome.

We had dinner near the Pantheon at the touristy, yet reliably solid, Napoletano’s Pantheon. Our waiter was hilarious, the view was timeless, and the food was terrific. It was the perfect finale for our epic adventure.

Day 12: Travel Day Home…..or not?
Literally – while we were zipping up our suitcases and about to leave for the airport, we got the email from Delta that our flight had been cancelled.  Seriously.  After a quick scramble, we were able to get a room that was actually a suite (so we didn’t have to pay for two rooms) right next to the hotel at the Hilton. Phew. Our current hotel graciously offered to stow our bags for us so that we could enjoy the day. So then the biggest dilemma became what to do with our “Bonus” day in Rome?!? We had a list of a few things we hadn’t made it to…
 
We started out walking through the Campitelli neighborhood, and past the ​Temple of Hercules Victor, and on to our destination: the Mouth of Truth.  The Mouth of Truth is a large, ancient Roman marble mask that is inside the portico of the Santa Maria in Cosmedin church, at the Piazza della Bocca della Verita. According to a medieval legend, it will bite off the hand of any liar who places their hand in its mouth. In the Middle ages husbands would bring their wives here to see if they were faithful. Ironic, since the church is also the home of St. Valentine. So of course, there is a line around the block of tourists waiting to put their hand in the mouth of the mask for Instagram.

The mask weighs almost 3,000 pounds and is though to depict the face of the seas god Oceanus. Historians are not quite sure about the original purpose of the mask, but it is thought to be a drain over from the nearby Temple of Hercules Victor, which had an oculus similar to the one at the Pantheon so it would rain inside. The disk was removed from the temple and placed against the wall at Santa Maria in Cosemdin in the 13th century.
 
From there we headed to the Jewish Neighborhood in search of lunch, but since it was the Sabbath we could only enjoy the beauty and history of the neighborhood.
In our search for a lunch spot we came across a lovely little island in the Tiber River called Isola Tiberina, and there we found ​Tiberino Ristorante. We had a truly European style, unhurried lunch here. It was fabulous – both the food and the people watching. In fact, this is where I saw someone go by with their little dog in an adorable little pink “adidog” sweatshirt, which I located on Etsy and ordered before the food even came.  Even Coco was going to have a cool souvenir from Rome!
 
From there we headed to the Catacombe di San Callisto, which were not what I expected – they were very different from the catacombs in Paris. They were the official underground cemetery of the Church of Rome in the 3rd century AD. Around half a million Christians were buried here, among them many martyrs and 16 popes. They are named after the deacon St. Callixtus who, at the beginning of the 3rd century AD, was assigned by Pope Zephyrinus to the administration of the cemetery. Since 1930 they have been entrusted to the custody of the Salesians of Don Bosco.
 
The parkland above the catacombs was truly beautiful, and we even saw flocks of wild green parrots! After some quick research, it turns out they are rose-ringed parakeets, which are not native to Italy. Apparently, there has been a feral colony of Rose-ringed Parakeets in Rome since ancient times. Ancient Romans, over hundreds of years, had captured a subspecies of these parakeets from Africa to use as captive novelties.  The birds are striking to look at and are capable of learning up to 250 words that could be repeated to entertain owners and guests alike.

We needed to head to our hotel, and since it was next to the airport we knew it would be a bit of a taxi ride. So for our last stop, we visited the cats at the Largo di Torre Argentina, one last time.
 
 
Day 13: Depart
 
​As you plan your own trip, please be sure to visit B visit my list of Top 10 Travel Essentials.
 
And as promised, here is my Restaurant list for Rome:Salumeria Roscioli
note: They also have Rimessa Roscioli next door – same food, more casual setup.  (This was our favorite restaurant of the whole trip. SO good! We even signed up for the wine club while we were there and it’s been great.)

Il Chianti Vineria
If they have the puntartelle salad….wow! Bitter and crunchy with anchovy dressing if you like that. I do!

Piato Romano
 La Gattabuia
Nannarella

And if  you have time, definitely go to the Jewish Ghetto for the artichokes alla giudia…but Roman style artichokes are also really delicious.
Giggeto al Portico Di’Ottavia

Nonna Betta is really good.

Ristorante Velavevodetto  *****This place is cool because it is built into a cliff that was basically a garbage heap for ancient people to dump their jugs and broken pottery. There are glass panels in the walls for you to see piled up ancient shards of pottery. (This recommendation came from my cousin while she was there on sabbatical.  They loved it, and it sounds cool but without a car it’s a bit far. Just something to keep in mind).