Confession: I Used to Be an Overpacker (Until Greece Taught Me a Lesson)

Let me tell you a travel truth that took me way too long to learn…

You probably do not need that giant suitcase.

I know because I used to be the queen of overpacking.

When I went to Greece, I packed a huge suitcase. I mean packed. Dresses for every occasion, multiple shoes, outfits I was sure I would wear, “just in case” pieces… all of it.

And guess what?

I ended up wearing the same two pairs of shoes the entire trip. Half the dresses never even left the suitcase. And dragging that giant bag from place to place? Not exactly the dreamy European vacation vibe I had imagined. 

That trip taught me something important:

Especially in Europe, less really is more.

When you are moving from city to city — trains, ferries, cobblestone streets, boutique hotels with tiny elevators (or no elevators at all!) — having a manageable suitcase makes travel so much easier.

There is something incredibly freeing about not hauling around a massive bag.

You move faster, You stress less.

And honestly? You enjoy the trip more.

Fast forward to my most recent trip to Mexico. I had learned my lesson… sort of.

I packed lighter and used a travel suitcase, but even then, I still came home realizing I did not wear everything I packed.

Why do we do this to ourselves?

I think we imagine every possible version of ourselves on vacation.

Beach version.

Fancy dinner version.

Cute brunch version.

“What if we go somewhere amazing?” version.

But the reality is, we usually gravitate toward the same favorite things.

The dress that feels good.

The sandals that are actually comfortable.

The outfit that works for multiple occasions.

And here is your permission slip:

It is completely okay to wear the same dress twice.

I promise nobody in Italy, Greece, France, or Mexico is keeping track of your outfits.

Actually, most Europeans travel much lighter than we do.

A simple black dress styled differently? Perfect.

A linen set you wear multiple ways? Amazing.

Comfortable shoes you can actually walk in all day? Essential.

I would rather my clients be comfortable, moving easily between destinations, and enjoying their trip than wrestling a 70-pound suitcase through a train station.

So now, when I travel, I ask myself:

Can this fit in a carry-on?

Not because I want less style — but because I want more freedom.

Less luggage.

Less stress.

More memories.

And trust me, after dragging a giant suitcase through Greece…

I learned my lesson.

Mostly 😉