A Winter Trip to Italy With Teens

Our family’s experience and recommendations for some hidden gems

By Jamie Ratner, President and CEO of Macaroni KID January 9, 2023

When I was researching winter break trips to Italy for teens I found very little information. So I decided I would write this article for anyone considering a trip to Italy with teens during the off-season.

Winter break is not the typical time for U.S. and Canadian families to travel to Italy because of the cooler weather, but we decided to give it a shot. 

I can now fully recommend traveling to Italy in the winter as a great trip option. We found it to be:

  • Much less busy than the warm weather months (we did not reserve any attractions in advance and never stood in a single line)
  • Much less expensive than the more popular summer months (all of our 4-star hotels ranged from $175-$350 per night)
  • Surprisingly affordable at restaurants (we paid less for meals out than we do in the U.S., plus we got the benefit of a strong dollar against the Euro!)
  • Magical. Italy at Christmas time is lit up with Christmas lights and festive markets.

This was my kids' first trip to Europe. I selected Italy as our destination because I felt it might be a good first European trip for them. I decided that based simply on the fact that my kids (like me) are big foodies, and figured the food in Italy would blow their socks off. But my kids are not very interested in history and visiting Italy can mean taking in a LOT of history.

So I worked hard to plan well and balance out the stuff they may find boring.

We started our 10 day trip in Venice, then headed down to Florence, and finished our trip in Rome. 

The weather typically gets warmer as you go south, so I think this route served us well as we warmed up as we went. When we arrived in Venice the temperatures were in the 40s and we wore hats and winter coats. The joy of shedding those with each stop was exhilarating.

We flew into Venice’s Marco Polo airport, and I arranged transportation directly from the airport to the hotel. 


We arrived late, but the experience of driving into the city was still mind-blowing for the kids when the driver pulled up and we had to walk across bridges and down dark alleys to get from our car to the hotel on the water. That vehicle from the airport was the last car we saw our entire time in Venice! In fact, the city was so empty that night you could hear a pin drop in the streets.

Our Venice hotel was Palazzo Veneziano

Palazzo Veneziano was super cool because it was a 2-level suite with a staircase that led the kids to their own upstairs bedroom and bathroom (though they shared a shower with us on the lower floor). The location was on the water and it was an easy walk to everything. Palazzo Veneziano was a great find for a family! 

When we walked outside early the next morning we were awed by how gorgeous the city was and how it was surrounded by water. 

For our first full day in Venice, I scheduled a 2-hour Family Friend Private City tour. 

It was a good way for us to learn a bit more about the city and figure out our way around for the rest of the time there. 

My teens immediately asked us why we took them on a “school trip” (on top of them dealing with jet lag so they were beyond moody!)…so I decided moving forward I would be limiting the tours to one per city as a compromise. 

After the tour, we hit some of the highlights including Doge's Palace and St. Mark's Basilica, and then we took a private gondola ride.

We finished Venice in one full day and left the next morning. It was enough time to see the highlights of this amazing but compact city.

One of the kids’ favorite parts of the entire trip was heading to the train station in Venice. We took a private water taxi to get there. It was such a unique experience. At the train station, we grabbed some breakfast and easily found our track. The train was very comfortable for our 2-hour journey to Florence.


When I asked my kids their favorite city on our trip? They both said Florence. 

We stayed at the Market Urban Hotel. It was very inexpensive, newly renovated, included a great breakfast, and was conveniently located near the train station.  I had booked a family suite but was upgraded when I got there to two single rooms (which I had read they do frequently!) for only $175 total per night. While the rooms were a bit tight, my kids were thrilled.

The city of Florence’s size felt manageable, but it included spectacular sites and the city center. 

I had planned entertaining activities since we were staying longer than we'd stayed in Venice. Some of the highlights:

  • A pizza and gelato-making class through Diadema Cooking School
  • Shopping for affordable Italian leather (I can’t wait to wear my new coat!)
  • Climbing the Duomo. 
  • Attending a match of Florence's soccer team 

My kids, who are soccer players, absolutely loved the experience of attending a soccer match for Florence’s team. 

The rest of the time we spent looking at Florence's sites. 

We did another private Family City Tour which was helpful for us to get our bearings and learn more history of this vibrant city. My kids’ eyes lit up when they saw David on the first night. I don’t think they imagined it could be that BIG and impactful. It definitely lives up to its hype! 

The city is also spectacular in its beauty. I think to me the most stunning views are of the Ponte Vecchio Bridge. All the jewelry shops lined along it make it look almost like a city on a bridge.

One other point to mention: My son is super into fitness and really wanted to work out in Florence. Since our hotel didn’t have a gym, we dropped him at KLAB which was just 5 minutes from our hotel and cost 25 euro per day. It was worth it because it kept him in a good mood, and we could easily drop him off pick him up. It was impossible finding a good gym option in Venice and Rome, so if your teens need a gym, this is a good choice for Florence (though if a gym is a priority, you may want to try to find a hotel that has one to avoid the hunt!).

Muy Buono!

We ate like kings the entire trip (the pizza, pasta, gelato, coffee, and baked goods were off the charts), but overall the food was best for us in Florence. 

Some of our favorites included:

  • Sandwiches from All' Antico Vinaio, where there is always a line! We found this restaurant as well in Rome but it originates in Florence – my husband Brian remembered how good it was from a post-college backpacking trip.
  • Dinner at Trattoria Zaza, supposably touristy but we really enjoyed it, especially the T-Bone steak which is big in Florence.
  • and L’osteria di Giovanni, which was probably our best meal. Plus we ate in a wine cellar! 

We also grabbed food from the super popular Central Market. My daughter had an insanely delicious burrata pasta there. Even on the cold days, we never missed a day of gelato the entire trip (and most days we had it twice!).

Traveling to Rome, via Siena and Orvieto

We hired a driver to take us from Florence to Rome. I found Italy Limousine and they were fantastic. My kids enjoyed the drive as it was scenic and comfortable, but they could have done without the two stops we made in Italian villages along the way. Brian and I thought the Italian villages were quaint and fun to get to explore and feel how different they were from the other city center. But on reflection, given the train is much less expensive, I might recommend going that route if you are traveling with teens. If it was just Brian and me, I think our plan worked well, but with the kids? The straight shot is probably a smarter choice.

The first town we stopped in was Siena. We walked up a large road to get to the square. We then walked to see their Duomo and grabbed coffee, juice and croissants at the museum’s cafe. Local kids were walking through the town center singing Christmas songs which was charming.


♬ original sound - JamieRatner

 Our next stop was the town of Orvieto. This town did have our absolute favorite gelato from the trip at a place right below the oldest clock tower in Italy.

We also got pretty lost trying to find the Well of St. Patrick but it was pretty cool and made for some great pictures — if your teens aren’t scared of heights or claustrophobic. We also checked out the Duomo de Orvieto which was gorgeous.


Our kids' favorite place we stayed was in Rome. All I have to say is WOW! We booked an apartment through LifeStyle Suites Rome

The building was in the heart of the city with amazing shopping, and it was literally right behind the Trevi Fountain. It was a very, very old building with an old-fashioned elevator but once we opened the crazy big door we were shocked by the incredibly modern and cool apartment on the other side.

It was enormous and came with a kitchen, family room, dining room, washing machine (amazing to have after already traveling for a week!), a powder room, a master suite, a bathroom, and two additional bedrooms, which meant the kids didn't have to share!  

It was clean and a dream to come home to every day after our long travels and days walking the city. If you can snag this one, I highly recommend it. It was a bargain (at least in winter time!) and made our Rome experience especially awesome.

What to say about Rome? It was huge, busy, and surprising. 

What I mean by surprising is that around every corner you turned there was another enormous historical site that blew your mind. It felt a bit like being in NYC but then running into these crazy sites that were hundreds or thousands of years old left and right. 

The big tourist attractions like the Spanish Steps and Trevi Fountain were packed, so I can’t even imagine what they must be like in the summer. Being a runner, I love exploring new places on my runs and Rome was one of the best running experiences I have had. 

The benefit of it was I was able to see all the sites through my run with no tourists around early in the morning. We also LOVED the weather in Rome. It was much warmer for us than Venice and Florence — around 60 degrees, which was great for my early runs!

We were in Rome the longest. There was a lot to see! My kids (and me too!) lost steam a couple of days in because it is just a LOT that required a ton of walking and seeing sites. We tried to blend in good meals and shopping with the sites to keep their engines running. 

We were able to do a tour of the Colosseum (which is off the charts), Palatine Hill, and the Roman Forum (this tour was longer at 2.5 hours since there is so much to see and tested my kids’ patience so you may want to try a shorter option or even see the sites on your own).


♬ Adventure - André Branney

We also visited Vatican City on Christmas Day which was pretty epic. Other highlights included a Christmas market on the Piazza Navona, a visit to the Jewish Ghetto, and a tour of the oldest synagogue in Europe. Of course, we also loved many of the big landmarks, like the Spanish Steps and the Trevi Fountain. 


♬ Santa Claus Freestyle Beat - Walter Landors

 The rest of our time in Rome was spent eating and shopping ... and eating some more. 

The food was mind-blowing. I pushed us to try as many new things as we could. There were amazing varieties of everything, from meat and cheese platters to pizza and pastas to all the incredible desserts. 

Our favorite meals in Rome were lunches at Emma’s Pizzeria and Boss. We had brunch twice at Ginger we liked it so much. 

Gelato was literally on every block and our favorite place seemed to be the chain Elisa’s. Though we learned when selecting gelato places the key is to typically avoid the chains, and not select gelaterias with gelato piled high with crazy flavors. We also learned to steer clear when the colors don’t match authentic, organic ingredient colors – for example, bright green for pistachio is a no-no because it means artificial flavors were added.

What was so great about all of these food experiences is we got time together as a family to just talk and connect without the push and pull of our crazy schedules at home (it also helped that cell phone service was never great!). 

Though if your kids are like mine, they will be happy to take some time off from the family dinners once back at home (OK, OK ... maybe we can use the break as well!).

As for shopping? It was fantastic. I really enjoyed how fashionable the Italians are and dress. They had the typical chains (high-end and basic) we have in the U.S., but they had so many cute boutiques we stumbled in time and time again.

Making memories in the unexpected moments

When I ask my kids about their favorite parts of the trip, they talk about the experiences.

My daughter is still cracking up over the fact a bird pooped on my face in Florence on the Ponte Vecchio Bridge at a gelato store, and she is still shocked by the fact she witnessed two taxi drivers pull their cars over in front of us on the street and get out and start kicking and strangling each other! 

And my son cannot stop laughing about how on the way home, when we had to sprint between flights to make our connection, he said we looked like penguins the way we were running. And then the excitement when we were randomly and miraculously upgraded to Business Class on the long flight home. Quite a treat for the kids! These are the memories we made as a family. Just being together on a trip like this makes traveling together so worthwhile…. especially with teens, who can be more difficult to connect with.

So yes! Book that off-season winter trip to Italy… it is a very economical, uncrowded, and magical time to go. Plus, you can put on 10 pounds and you will have months to lose it before you need to wear a bathing suit again! 

Enjoy! Arrivederci, ITALY!

Jamie Ratner is the CEO of Macaroni KID, CertifiKID and Hulafrog. She lives in Maryland with her husband, Brian, and their two children. Jamie and Brian's book about their entrepreneurial journey, ParentPreneurs: A Decade of Deals From A Messy Minivan, was released in 2022.