What Italy Taught Me About Letting Go of the Itinerary

I'm a professional photographer who travels with women for a living. I design small-group trips, show up as the host, and document everything along the way. This past April, I spent ten days in Italy, first in Florence and then in Cinque Terre along the Italian coastline.

It was a trip I had been dreaming about since I was a teenager. My dad's family is Sicilian, and Italy has always felt personal to me in a way I can’t fully explain. Getting there because of my camera made it that much sweeter (and so did the gelato).

Florence, Both Times

Florence was my bookend on this trip. I flew in and out of the city, spending one night on the front end before continuing on to Cinque Terre, and returning for a final night before flying home.

On the first pass, I spent my morning walking. The city wasn't fully awake yet, and the alleys were quiet and golden and everything I had spent years imagining through a camera lens. I had dreamed about capturing those streets since before I even owned a camera. Standing in them for the first time, I had to keep reminding myself it was real.

But Florence didn't fully reveal itself to me that morning. I moved through it like a visitor, and left for Cinque Terre, half-wondering what everyone meant when they said there was magic in that city.

Spoiler Alert: I found out on the last day. And it wasn't what I expected.

The Week in Between

Cinque Terre is unreal.

Five colorful villages stacked up the cliffside along the Italian Riviera, each one more charming and beautiful than the last. We stayed in Manarola for the first few nights, in a hotel that was formerly the owner's family home. That detail mattered to me. It's the difference between experiencing a place and just passing through it. Talking to the current owner about the home’s history and storied corners was a favorite pastime of mine each morning over breakfast.

The moments I carried home from Cinque Terre are not just the postcard shots. The moments I remember most are the seemingly small ones.

Saying “buongiorno” to the nonna hanging laundry out her window above the alley, who waved back and called back the same. Chatting with the hotel owner about what the village looked like before Rick Steves sent the tourists. Watching Italians talk to each other with their whole bodies and wondering, are they angry or just being Italian? The answer, I learned, is simply an expressive Italian.

And then there was the sunset boat tour on our last evening, riding along the coastline at golden hour while a man who was born the same year as me, but lived an entirely different life, told stories of his childhood in these villages. All five of them glowing orange behind us. New friends around me on the water.

That's the moment I'll close my eyes and still see in twenty years. That and the lemons. Italy has lemons everywhere, enormous and improbable, and I loved every single one of them.

Getting Sick in Paradise

I want to be honest here, because I think travel content that only shows the beautiful parts does everyone a disservice.

I got sick. Really sick. Food poisoning, a dairy mishap (I’m allergic to milk protein), or most likely both. I spent 18 hours in bed at one point while the rest of the group was out exploring. I missed things I wanted to see. I was exhausted, frustrated, and very far from home.

And then on day five, during our e-bike tour up the mountain, my body staged what I can only describe as an unauthorized evacuation. It was the most humiliating experience of my life, and I will be dining out on that story for years.

I recovered on a beach in Monterosso with a book in my hand and the Mediterranean in front of me. Sometimes that's the reality of travel.

The hard days are part of it, too. But the good days make it all worth it. Honestly, if I’m going to be sick, it might as well be somewhere amazing.

Four Books and One Sentence

I read four books on this trip. Four. A personal record, and one I'm genuinely proud of because I had been wanting to get back to reading for a while and kept finding excuses.

Turns out airplanes and trains are the cure for every excuse.

I started the first book somewhere over the Atlantic and finished it before I landed in Florence. The second was done by my first full day in Cinque Terre. The third I read on that beach in Monterosso while I was recovering. The fourth I started in Florence and finished somewhere over the ocean on the way home.

I've been thinking about one sentence since the moment I read it, somewhere over the Atlantic on that first flight. I'm not going to quote it exactly, but the idea was this: it's not the big memories you should be chasing. The small ones are the fabric of your life. Remember how you felt when you were making them.

Italy proved that true every single day.

The Last Afternoon in Florence

My last full day in Florence, I had every intention of staying in my hotel room.

I was exhausted. My stomach was still settling. I had nothing specific calling me outside and no energy to go looking for it.

Instead I did what I always do when I need to move through a big city without getting completely overstimulated. I put in my AirPods, scrolled to a calm vibe on the playlist, and walked out the door. Olivia Dean was the soundtrack to the whole trip, starting on the first flight out and carrying me through Florence alleys and Cinque Terre coastal paths all week. There is something about the right music in a new place that makes the whole experience feel cinematic. I love that anytime I hear this album in the future, I’ll be instantly transported back to Italy.

I found a bookstore. I collect Peter Pan editions, and I ended up in a long conversation with a young woman who worked there about her favorite versions the store carried. She was wonderful and enthusiastic and exactly the kind of person you hope to meet when you wander into a bookstore in a foreign city. I bought one in Italian. It's the first in my collection in a foreign language.

My little brother and sister-in-law are expecting their first baby, and standing in that bookstore, I made a quiet decision. My niece or nephew is going to grow up with a library of books that their aunt has found for them from all over the world. I bought the first one on this trip. A board book of Pinocchio in Italian, illustrated simply and beautifully, from the city where the author was born.

Then I wandered past a restaurant just outside my hotel. It was the start of the Italian afternoon pause, when most small shops and restaurants close for a couple of hours. The owners saw me and waved me over anyway. The kitchen had already closed, but they insisted on feeding me bread and a simple salad with chicken and balsamic at a red checkered table while the street hummed quietly outside. It was exactly what my stomach needed after a week of pasta.

At the end of the meal, I asked where I might find good olive oil to bring home for my mom. They disappeared into the back and came out with two tins from their personal stock, from a family farm in Tuscany they love.

I sat there in gratitude, thinking about how small this great big world can feel.

What Florence Finally Gave Me

Florence hadn't called to me the way people said it would when I passed through on the first day. So many women had told me there was magic in that city, and I had moved through it like a tourist who was looking in all the wrong places.

I found it on the last day. When I was tired and had no agenda and was simply existing. Not trying to make the most of my time. Not optimizing the hours I had left. Just walking around and letting things come to me.

The bookstore conversation. The board book for a baby I already love beyond understanding. The restaurant owners who fed me and sent me home with their olive oil.

None of that was on an itinerary.

What This Means for the Way I Travel With Women

I think about this a lot when I'm designing Say Yes trips.

My job isn't to fill every hour. It's to create the conditions where the unplanned moments can find you. Small groups so there's room for real conversation. Enough free time to wander. Accommodations that feel like somewhere, not just anywhere.

The women I travel with don't need me to show them every famous thing in a city. They need me to help them feel settled enough to stop looking and start noticing.

That's where the good stuff lives.

If You've Been Waiting for the Right Time

If you've been dreaming about a trip and waiting until you have more energy, more money, more time, more certainty that it will go perfectly, I want to gently offer you this:

You don't have to be at your best. You don't need a full itinerary. You just have to walk out the door, with or without AirPods.

Sometimes that's really all it takes.