In October 2024, I did something I had never done before.

I took myself on a trip.

Not for work. Not tacked onto something else. Not because it made logistical sense. Just… because I wanted to go.

I was meeting friends in Madrid to visit one of their daughters studying abroad, but I had a few extra days. So I went to Portugal first. Porto had always been on my list.

Flying from the West Coast into Europe is what it is. You land during the day, exhausted, and the only real strategy is to stay awake and push through.

So that’s what I did.

I checked into my hotel, grabbed my raincoat and an umbrella, and went outside with absolutely no plan.

It was raining. Steady, quiet, beautiful rain. The kind that makes a city feel softer.

I wandered. I had lunch at a small place I can’t remember the name of, but I remember exactly how it felt to sit there. Warm. Alone, but not lonely. Fully there.

And then the rain picked up.

I found myself standing outside a cathedral. I didn’t know what it was. I didn’t look it up. I just knew I needed to get out of the rain.

So I went inside.

What I didn’t expect was what happened next.

Almost immediately, I felt this overwhelming sense that my mom was with me.

My mom died 20 years ago. She was 60 (yep, that sucks).

When I was in college, she received a small inheritance from my great-grandfather, with one request: do something for the girls. So she took my sister and me on a month-long trip to Europe. London. Paris. A bus tour through Lucerne, Venice, Florence, and Rome. (The bus tour… questionable. The experience… unforgettable.)

I think about what that trip meant to her. We had tea at the Savoy in London. And she talked about her mother, my grandmother Queena, who had always dreamed of her daughters traveling to far-off places. That didn’t quite happen for Queena’s generation. So my mom made sure it happened for ours.

Now, 30 years later, I was standing alone in a cathedral in Porto.

Surrounded by intricate tiles, soft light, and something I can only describe as energy.

I’m not particularly religious. But I stood there with tears in my eyes, completely certain of one thing:

My mother was with me. And she was so happy I had taken myself on this trip.

The next day, I had a photo shoot scheduled.

Months earlier, while planning the trip, I’d come across Flytographer, a company that connects travelers with professional local photographers around the world. It felt like a splurge. I booked it anyway (because, of course I did), with this quiet thought: I may never do something like this again.

The weather wasn’t cooperating. It had been raining on and off all day, so I did what any self-respecting traveler should do — I got a blowout. (Full credit to my friend April, who insists on this and a walking tour in every new city. She’s right.)

I spent most of the afternoon on WhatsApp with the photographer, watching the sky. Finally, he dropped a pin. Meet me here around 3:00. I think we’ll have a break in the rain.

So I did.

He led me up a hill, around a corner, and suddenly, I knew exactly where we were.

Right back to the cathedral.

“This is the most beautiful place in the city,” he said.

I was covered in chills. Because it wasn’t just beautiful. It was already mine.

And then I looked up.

It had been raining all day. On and off, gray and heavy, the whole city under cloud.

For the entire shoot – every single frame – the sun came out (I have tears in my eyes remembering it).

The moment we finished, it started raining again.

I don’t know what to call that. I just know what it felt like.

What I love about these photos isn’t just how they look. It’s what they hold.

The arches. The tiles. The hidden corners of Ribeira. The color and texture and light.

But more than that… whoa, the feeling. I wasn’t performing for the camera. I wasn’t trying to capture something. I was already inside it.

That day lit the fire. It’s what made me fall fully, completely into travel. Not just as something I loved, but as something I wanted to build the next chapter of my life around.

Now, when I’m planning trips for clients, I think about that moment all the time.

Because here’s the thing: you’re already investing in the trip. The flights. The hotels. The experiences. The time.

What if you also invested in remembering it properly?

Not blurry selfies. Not asking a stranger and hoping for the best. Something you actually want to frame.

The best travel photos aren’t about proving you were there. They’re about remembering how it felt.

If you’re planning a trip that means something, I’ll probably suggest we build something like this in. Not because it’s trendy. Because some moments deserve to be held properly.

Flytographer is one of my most-recommended additions to any meaningful trip. Use my link for a discount on your first shoot.