I hadn’t been to Italy in 30 years since I had studied abroad in Florence myself during the 2nd semester of my junior year. I was so excited to go back this time, at 52, with my wife, our younger son, Harper, and to visit our 21-year-old son, Auden, who is having his own study abroad experience there during his junior year of college. These are the experiences that I value most in life. I talk a lot about experiences over things, and here was that opportunity.

There’s a statistic that’s gained a lot of traction lately about how once your children are past the age of 18, you will have spent something like 80% of the time you’re ever going to spend with them.

That has hit me hard for a long time now, especially because I know how valuable time is, having lost my own father when I was just 17. So we’ve made it a point in our family that our standard is to be on the other side of that statistic. We’re going to spend at least 2 months out of the year together, the 4 of us. It might be 1 or 2 days here. It might be 10 days in Italy. It might be a summer rental. It might be Kate and I moving and renting a place closer to where the boys are living. We’re going to do everything in our power to hold that standard.

And here was an opportunity for 10 days together, the 4 of us, that we were going to make the most of. 

And it was glorious. 

If you follow me on Instagram, you saw all of the pictures from all of the sights – probably too many, with me throwing up all over social media daily.  But here’s what I really feel and genuinely believe to be true: That my wife is stunning, and crushing it at 55. That I’m blessed with 2 incredible sons. That they have different personalities and skill sets and styles that bring life and joy to our lives and complement one another. That they’re both young men of character and have a unique closeness and bond.

I’m proud of that.  And I hope every father feels the way I do when they look at their kids. 

Kate found an incredible apartment in Rome. We ate our way through that city with enough pizza, pasta, lasagna, and tiramisu to deplete the country’s reserves. We walked and walked and shopped and toured and laughed and loved and hugged and exhausted ourselves so that we went to bed exhausted – the good kind – and woke up with energy every day.

I loved the Colosseum. I cried in the Jewish ghetto of Rome. The afternoon that Harper and I walked down the Spanish steps and into the hottest shopping area I have ever been in, boutique after boutique. The random gelatos, and there were a lot of random gelatos. The train to Florence, our apartment in Florence that Cameron Herold recommended, which was stellar. The jokes about David at the David. Finally finding protein and bistecca Fiorentina so I could gorge myself with something other than more pizza, lasagna, and pasta. The train to Bologna. The canals. The views. It was special. 

And it was us.

And with all of the awesome stuff, there’s also always something you’re not seeing. There’s always more that’s under the hood. And that’s the reality of family, and that’s the reality of life; and midlife, you get it all.

The other side of the coin…

We had at least one argument every day. Harper was sick one day and didn’t want to get out of bed. Kate was sick most of the trip—coughing and sleeping poorly. I found myself at the pharmacy on four different occasions for cold medicine, Ibuprofen, and Band-Aids for blisters from all the walking.

We were in a fifth-story walk-up with 4 bags at almost 50lbs each. I was taking them up and down the stairs. We couldn’t agree on restaurants half the time. I have one son who only eats cacio e pepe and pizza, another who will try anything and a wife who basically just says “I don’t care, I just want something good” and never defines what “good” is and in reality cares very much because every time i pick something I think is good, she asks the waiter twenty in depth questions about each dish in english and he only speaks Italian and just keeps saying “its good” back to her and she doesn’t believe him either. 

Hell, we couldn’t even agree on where to get coffee in the morning. I like this one little coffee shop I found around the corner from our apartment. Why? Because there’s a beautiful young, well dressed Italian woman with an incredible smile who welcomes me with a big “Bongiorno” each morning and I suddenly don’t feel like an invisible middle aged man anymore… Kate just wants a triple shot cappuccino from Guido on the other corner…So guess what? I’m going to both. Before 8 o’clock in the morning.

We have a 21-year-old and an 18-year-old who both think they know more than their 55-year-old mother and their 52-year-old father. But the real point is that there’s always something you’re not seeing. I love my family deeply and dearly, and we had an incredible time overall. But are they a picnic? No. Is it rainbows and unicorns? No.

Being the man of the family, I feel a ton of pressure. At 52, I still don’t feel comfortable with it all, how I got here, how fast it all has gone and how I’m somehow responsible for my family’s overall well being.  While Kate and Harper were shopping, Auden and I took a walk around Florence. Those laps through the city as we were winding our way down the cobblestone streets along the Arno were one of the most valuable times of my life.

We had a conversation about being a man, about the responsibilities and pressures and obligations that come with being the head of the household. We talked about the choices you make in life, and the opportunities and pride in what you take on. I told him about being in this world and how you have to lean on other people, on other men, whether you have a father in your life or not. How important it is to find your mentors, your advisors, those who can provide some guidance to help shape you into the man you want to become.

I encouraged him to observe behaviors, attitudes, and characteristics of individuals that he admires—or doesn’t. It was the kind of father-son conversation I wish I’d had with my own dad.

And how it never really goes away.  You just get better at handling it all.  I worry before we get on the plane. I worry if the credit cards are paid off. I worry if we have enough cash. I worry if where we’re staying is going to work out well. I worry if everybody’s healthy, if everybody’s happy, if nothing’s going to go seriously wrong.

I worry if Auden’s doing well in school. I worry if Harper’s going to be punished for missing too much school. I worry if Kate’s going to feel better and not have her health ruin the trip for her. And yeah, I worry that it costs $1,000/night to be there and everyone’s not cheery all the time, which I know is unrealistic. Deep down I think, “this costs a lot of money, suck it up.” I think every dad has those thoughts on trips like this.

I also crave time to myself, so I’m up at 6 AM to stretch, do some bodyweight movements, get a little work done, my breath work, read a few pages of a book, get coffee by myself before I bring everybody else’s coffee and stuff. I need that. I need to feel like myself and without being in a gym and eating pizza, pasta and tiramisu every day, I was a bit off kilter. 

Harper and I shared another moment together in a small way. We sat down, just the two of us, in a little sandwich shop to have a piece of pizza and a snack. The gentleman asked if we wanted some wine with that, and I looked at Harper and he looked at me, and for some reason, we both said okay. This was the first glass of wine I’d had in three years. It’s the first glass of red wine he’s ever had.

We sat there and laughed and enjoyed the fact that we both didn’t enjoy the wine at all. Our lips puckered at the taste of alcohol and wine—when you haven’t had it for as long as I have, and when he doesn’t appreciate it or want it at all. And it was that simple moment, having this shared experience together, that really signified what it means to be a dad.

We spent three days in Rome, five days in Florence, and then two getting out of Rome. And as great as it was in so many areas, I really don’t love cities anymore. 

I think I’ve kind of outgrown city life. I like beaches and mountains, and a slower pace, and less concrete and fresher air.

But if you gotta be in a city, Florence is about as good as it gets. It’s beautiful. It’s historical. It’s the nice kind of concrete that’s been around forever. For centuries, the architecture is stunning. The people are nice. The cold crispness of the air—even when it rained, there was something cool about Italian rain. The way everybody dressed and was walking through it, and it wasn’t interrupting anything at all.

I love small, personal, family-owned restaurants. So that was wonderful. The quality of the food was excellent. Although, I don’t want to see another piece of pizza or pasta or tiramisu for at least six months.

My favorite part of the trip was lying in bed with my boys at the end of the day, fully exhausted, between them, just being together and cherishing those moments—the ones that I wish I had with my own dad. And the closeness that my boys have as brothers.

There was a carousel in Piazza Signoria in Florence. And at night, in the rain, as we were walking home, I made everybody get on it. And we rode the carousel together in full ridiculousness. There was a guy selling roses there and as we circled around I reached out and grabbed a couple for Kate…It took both the street vendor and her by surprise…And yes, I paid him when we got off…And it made me happy. Like, really, truly, deeply happy.

And there was some retail therapy, and I hate retail therapy. I bought Kate a bag that she wanted and it was ridiculously expensive from Yves Saint Laurent. Consider it an anniversary present, Valentine’s Day present, a European vacation present. These things make her happy. I see them and I think, ‘that bag represents a week-long surfing trip in Costa Rica’ and kind of makes my head explode, but to each his or her own.

This trip was different. Incredible. Amazing. But different. And that’s what family trips are and what family dynamics are. Not exactly what you see on Instagram. There’s always something you’re not seeing. There’s always more to the story.

And that’s exactly the way it should be.