What’s the Best Way To Road Trip Through Italy With Young Kids?

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What’s the Best Way To Road Trip Through Italy With Young Kids?

Some may look at this title and question and immediately think it’s a joke. What’s the best way to road trip through Italy? WITH KIDS?

You will commonly hear people respond with the answer, “leave them at home!”

Depending on your kid, that may be a sound plan. However, don’t underestimate the travel capabilities of your youngsters. If you can work it where you can give them the experience of visiting somewhere new, don’t be scared to do so.

I know that not all children are good travelers. However, I was blessed to have two littles that travel better than most adults. In fact, during our two weeks of trekking through Italy, there were many times that they handled the things that were thrown our way better than the adults.

There are several things we implement to make the experience more enjoyable for the kids (and ourselves). We try to pick things that will interest them as well as us. We also bring snacks from home to supplement what we get in our travel destination. Additionally, we buy lots of snacks when we get there to keep their bellies full and reduce the chances of being angry.

Choosing Our Destination

When I first proposed that 2023 would be our year of travel, I gave my husband the choice of where to go first. Now, this isn’t just because I’m a fantastic wife. Obviously, that is true, but I also just wanted to explore the world and didn’t care where we landed. After having the itch to travel for so long, landing in the middle of the desert would have been fine by me.

That’s an absolute lie. The desert is in our plans for 2024, and I don’t know how well my fair skin and gingerness will handle it. I have time to figure it out, but it’s likely to involve SPF 200 and eight gallons of water.

And in another bout of transparency, I had a pretty good idea that he would pick Italy. And honestly, who doesn’t want to go to a land of incredible food and exquisite coffee? Sign me up!

This may come across as a surprise to none of you, but Italy has a lot to see. There is so much history in that one country, and those landmarks aren’t exactly right next to each other. Since I was just learning about travel hacking, there weren’t a lot of points at our disposal. So I wanted to be smart with our money and find the best deals.

It Wasn’t All Flowers and Rainbows

Let’s start off by saying that mistakes were made. And they weren’t all my fault. While flying into Milan was a sound choice, selecting a Maserati as a rental could have saved some Euros…

I want to outline all the highlights and the things that could have been done without, and that will take more than one post. This blog will give an idea of the itinerary we (I) came up with and our travel plans. This part was one of the most time-intensive, and tough decisions had to be made for our road trip through Italy. One of the hardest was realizing we needed to forego Pompeii because of insufficient time.

After that, I will break future posts down into each city and some critical stories throughout the trip that must be told. So, buckle up!

We Got Our Start in Milan

Our trip started in Milan, but we flew out of Chicago. What ticks my ticker more than anything is that flying out of Detroit costs more than driving to Chicago. Thankfully, we are in a place where it’s a pretty equal distance between both cities, but with tolls and traffic, Chicago always takes longer.

This would also be a good place to insert my horror story with KLM Airlines, but that deserves its own post. Stay tuned.

Our flight went ORD to JFK and then on to Milan. Once we got on the plane at JFK, I felt like I could finally breathe, but it took my husband telling me everything was fine and I could relax before I got to that point.

Again, when the blog comes out with that story, you will truly understand the insanity they put us through. You just wait.

We spent two nights in Milan right off the bat. And honestly, I think it was my favorite stop. We stayed a bit outside the city, so it was quieter, and the food prices were much lower.

Florence and the Leaning Tower of Pisa

After two days in Milan, we continued our road trip through Italy. We hopped in the Maserati (insert eye roll) and drove to Florence. On the way, we made a pit stop to check out the Leaning Tower of Pisa.

Yes, it is still leaning. Yes, we have gotten that question a lot.

Something very new to us was that certain areas within the city are closed to cars throughout the day. Therefore, we had to structure our arrival time to account for these restrictions. Were we successful in that? Kind of. Did we white-knuckle drive through Florence’s incredibly narrow back alleys and almost take out a slew of citizens? Yes. Did Jacob nearly drive on the train tracks as he tried to find parking for the car? Absolutely.

However, the location of our Airbnb was incredible. It was in the city’s center and within a few minutes walking distance of anything you could want. We learned that Airbnb in Italy is bound by different requirements than those in the USA. Case in point, they have to provide breakfast. This ranged from excellent (our Rome host had milk, juice, cereal, cookies, yogurt, bread, and more for us) to not-so-great (Venice offered us stale crackers and no coffee maker).

These items were especially helpful when that jet lag hit, and we were without the energy to go across the street to a restaurant. This happened on our first night in Florence. The kids and I were basically lethargic in one room after eating Corn Flakes for dinner while Jacob and our travel partner Kasey went across the street to get dinner.

On To Rome!

After two nights in Florence, we went on to Rome. Like Florence, Rome has the same restrictions where you can’t drive in certain areas at specific points of the day. Also, we were supposed to reserve parking in advance and failed to do so. Also, our host sent us a pin drop of his location, and the GPS sent us completely across town. Still not sure how that happened…

With the residential streets in Rome, you can’t drive all the way to where you are staying. Therefore, Jacob had to stay in the car while it was double parked on the side of the road while the host, myself, Kasey, and the kids hauled our luggage down several cobblestone streets to the Airbnb. After getting in, the host returned to Jacob and drove with him to find parking. They then had to walk back to us with the remaining luggage.

Let me continue this story with the fact that the host made it very clear to myself and Jacob on the last day in Rome that we COULD NOT drive on those roads. He told us that there were cameras and that we would likely get a ticket if we were to do that. Guess whose husband didn’t listen and did it anyway? Also, guess whose husband received a citation in the mail from the Italian government for parking illegally? That’s a souvenir from our road trip through Italy that we didn’t want.

There Were Some Downfalls

One of the most devastating things about our time in Rome was not being able to hear the Pope speak. We had the tickets, and we got there in time, but the guide left early and wouldn’t come back for us. We called and complained and got our money refunded, but the Pope talk went on without us.

One thing that was abundantly clear during our time in Rome is that we should have stayed a bit more removed from the central area as we did in Milan. The cost of food at restaurants was significantly higher, and they definitely took advantage of our tourist status. I also didn’t feel as safe in Rome as I did in the other two cities.

On to Venice!

I had really high hopes for Venice. Unfortunately, those hopes didn’t pan out. We only had one night there, which wasn’t enough time. But we were also there during Carnival, and the number of people visiting was insane. I obviously don’t have anything to compare it to, being that I’ve only been there the one time, but it was chaotic.

I will also say that there is a 100% chance that I would not be able to find our Airbnb on my own. Think of all the movies you see where there’s an intense foot chase, and they are weaving in and out of narrow back alleys. That is Venice. Add in the fact that there is basically no lighting, and the walkways are all cement and brick from the housing exteriors.

Confession: We got lost when we left our Airbnb to go to dinner. Thankfully, a police officer who understood a few words of English helped us.

Getting to Venice was an obstacle as well. Everywhere we went in Italy, we were greeted by people who were overjoyed to help us in any way we needed. That is until we came to Venice. Nobody would help us find the right place to go. The ferry was closed, and then the shuttle wasn’t accepting payment because it was cloudy. It was incredibly frustrating and didn’t help us to view Venice in a favorable light right from the get-go.

Back to Milan

After Venice, we went back to Milan to fly home, as it was the end of our road trip through Italy. We stayed in the same hotel. However, it’s worth noting that European hotel chains abide very strictly to occupancy rules. When we booked the hotel, we stated that two adults and two children would be there. Then it was decided Kasey would be with us. I contacted Hilton and asked them to add him to the reservation.

However, when we got to the hotel, we discovered that corporate didn’t inform the hotel of this change. They were able to accommodate us, but there are times when guests have lied about how many people are sharing a room and are kicked out when the truth is found out.

Because of this, we just booked a separate room to stay in on our return to Milan. I offered it up to myself and allowed the guys and the kids to take up residence in the other room. Mine had a balcony, but theirs did not. It was glorious, and I regret nothing about that decision.

In the Air Again

After our night in Milan, it was time to start our trek back home. Unfortunately, due to the issues with KLM and also Air France, this was no small feat and involved an overnight stay at the Amsterdam airport. There will be much more about that fiasco in my Italy travel vent post about KLM. You won’t want to miss that!