Memory-First Travel: Why I Always Leave Room for the Unexpected

Dan, Livi, and Christianne at the Australian Open. Image by Dan Sattel

I’ve learned something after years of traveling the world with my family and for my career:

Some of the best parts of a trip are the ones you never planned.

Don’t get me wrong- I love a good itinerary. There are restaurants that deserve reservations months in advance, museums that require timed entry, and experiences worth planning your entire trip around.

But I’ve also learned that if every minute of your vacation is scheduled, you leave no room for discovery.

One of the ideas I recently shared on ABC News is what I call Memory-First Travel- a philosophy centered on prioritizing meaningful memories over simply checking off attractions. One of the easiest ways to create those memories is by protecting open space in your itinerary, allowing room for the unexpected to become part of your story.

Not because you don’t know what to do- but because you don’t know what you’ll find.

One of my favorite examples happened in Melbourne, Australia.

We realized we were in town while the Australian Open was underway. It wasn’t part of our original plan, but we checked for tickets that morning, found seats, and decided to go. A few hours later, we were watching one of my husband’s favorite players, Novak Djokovic, win live. That single spontaneous decision became one of the highlights of our entire trip.

The same thing happened in Sydney. We discovered Jesus Christ Superstar was playing while we were there. We bought tickets that afternoon, walked into the theater that evening, and left thrilled that we were able to see some of the best theater we've seen in years.

Those experiences weren’t on our itinerary, but they’re now on our list of favorite memories.

Sometimes the unexpected isn’t a major event; it’s simply slowing down enough to enjoy where you are.

Expecting the unexpected: feeding an Indian Rhino in Singapore. Image by Dan Sattel

In Singapore, we spent the evening wandering through the Night Safari instead of rushing from one activity to the next.  There, we hand-fed an Indian rhino bok choy, walked among clouded leopards, and listened to an African Lion roar across the entire park.

In Mexico, some of our favorite meals didn’t come from reservations at all. We followed a local’s advice and went outside tourist districts to find the best and freshest seafood at a local food truck, trying one incredible bite after another and talking long after dinner was over.

Wandering through Venice, Italy led to unexpected connection with locals. Image by Christianne Klein

In Venice, we wandered away from the tourist-filled streets and found ourselves in neighborhood bacari, sharing cicchetti with locals. Before long, everyone was singing Bailando together. We hadn’t planned to spend our evening that way, but it’s one of the first stories we tell when people ask about Venice.

And then there’s Florence.

After an incredible Steak Florentine dinner, my husband and I kept walking. We eventually found ourselves outside the Uffizi Gallery late at night, where the statues stood beautifully illuminated against the evening sky.

We grabbed a couple of Negronis and sat outside, listening as music drifted through the city. Before long, we were dancing together right there in the square.

It wasn’t a scheduled experience.

It wasn’t something we booked.

It wasn’t even something we expected.

It was simply one of those moments that remind you why you travel in the first place.

I think we’ve become conditioned to believe that the perfect vacation is the one where every minute is optimized.

Every attraction. Every reservation. Every hour.

But some of the greatest travel memories begin when you decide not to look at your watch.

Leave an afternoon open.

Say yes when something unexpected comes along.

Take the recommendation from the local instead of the one with the longest online reviews (and do this at least once every trip).

Because the places you’ll remember most aren’t always the ones you researched for months.

Sometimes they’re the ones you accidentally discover.

When people ask me about our favorite trips, it’s often those unexpected moments that stay with us and ones we share first. 

I talk about watching Novak Djokovic win at the Australian Open because we happened to be there.

I talk about buying tickets that day to Jesus Christ Superstar in Sydney.

I talk about food trucks in Mexico, singing with locals over cicchetti in Venice, and sharing Negronis outside the Uffizi Gallery before dancing together under the Florentine sky.

None of those moments were on our itinerary, but every one of them is part of our family’s story now.

That’s what Memory-First Travel means to me.

Not checking off more boxes.

Not seeing more attractions.

Simply leaving enough room for a destination to surprise you.

Because sometimes the memories you’ll treasure most are the ones you never saw coming.