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When Travel Doesn't Go as Planned: A Capri Story and the Idea of a Do-Over Trip

  • Writer: Alison Friedman
    Alison Friedman
  • Apr 14
  • 2 min read
Woman in sunglasses and blue dress smiles on a sunny balcony with colorful hillside buildings and blue sea in the background.

Almost exactly a year ago, Scott and I were in Capri for two days before meeting our boys on the Amalfi Coast.

 

And I joke with him all the time.

I want a do-over.

 

Not because Capri wasn't beautiful. It was.

Not because we didn't plan it well. We did.

 

But because I was sick.

 

Like really sick.

 

I had a stomach bug, and being in Capri, of all places, and not being able to eat felt almost ironic. I had zero appetite, which if you know me, never happens. At one restaurant, I think I managed half a ravioli. Half.

 

Instead of long lunches and lingering over meals, I was focused on one thing.

Where is the next bathroom?

 

It completely changed how I experienced the trip.

 

There were things I didn't do because I didn't feel comfortable being too far from a bathroom.

The chairlift in Monte Solaro.

A boat day around the island.

Even certain walks and hikes.

 

I was there, but not really there.

 

And now, almost a year later, feeling a little under the weather again, thankfully not the same kind of sick, it brought me right back to that trip.

 

It made me think about something we don't talk about enough.

 

Sometimes travel doesn't go as planned.

 

Sometimes you wait for the trip, look forward to it, plan it, and then life throws something completely unexpected your way.

 

And you don't get the experience you thought you would.

 

But here's what I've come to realize.

 

That trip still counts.

 

It's still part of the story.

Even the imperfect, uncomfortable, not how I pictured it moments.

 

And maybe that's part of adventuring too.

 

Not just the highlight reel, but the real life that happens in the middle of it.

 

Do I still want a do-over?

Absolutely.

 

And maybe I'll get one.

 

But even if I don't, that version of Capri, sick, slower, limited, still gave me perspective I wouldn't have had otherwise.

 

It reminded me how much I value feeling good in my body, especially when I travel.

How much food, movement, and energy shape our experiences.

And how quickly that can shift.

 

So here's to the adventures that go exactly as planned

and the ones that don't.

 

Both count.

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