The Carry-On Edit

Italy is officially getting close enough that I’ve entered packing mode.

Not actually packing for Italy yet — because between now and then, real life is still happening. There’s work travel, a long weekend Up North in Gaylord, and, you know, my actual job and life to manage.

And this is exactly why, despite being a devoted carry-on traveler, I own multiple suitcases.

Yes. Multiple.

I know that sounds slightly ridiculous coming from someone whose entire travel personality is basically “I can fit it in a carry-on.” But hear me out.

When I have trips stacked close together, the last thing I want to do is come home, completely unpack one suitcase, do three loads of laundry and immediately repack the exact same bag for somewhere else.

So I rotate.

One suitcase can be staged for Italy while another handles a quick Michigan weekend or work trip. It lets me start packing for a big trip early without disrupting everything I need for the trips happening before it.

Italy gets the long game.

For Italy, I’m thinking through outfits now: what can be reworn, what layers well, what works with the same shoes and what I’m realistically going to want to wear after walking all day.

I’ll be gone for two weeks and moving through Perugia, Siena, Lucca, Florence and Rome, so every item has to earn its space.

My Italy suitcase becomes almost like a holding zone. As I decide something is definitely coming with me, I can set it aside instead of accidentally wearing it the week before I leave and realizing the night before my flight that it’s sitting in the laundry basket.

Been there.

Up North is a completely different packing personality.

A long weekend in Gaylord, Michigan requires almost none of the same strategy.

This is the easy suitcase.

Jeans. Comfortable layers. Sneakers. Casual clothes. Something cozy because Michigan loves to remind you that summer can turn into fall approximately seven minutes after sunset.

I don’t need perfectly coordinated outfits or a carefully edited capsule wardrobe. I need clothes that are comfortable, practical and can handle whatever the weekend turns into.

And then there’s work travel.

Work trips are their own category because I don’t want to borrow too heavily from either suitcase.

I need my work clothes, shoes, toiletries and travel essentials ready to go without dismantling the Italy packing I’ve already started.

That’s where having multiple carry-ons starts feeling less excessive and more like a system.

One is the upcoming big trip.

One is the current trip.

And sometimes there’s a third sitting there waiting for me to decide what exactly its job is.

Is owning several carry-ons necessary?

Absolutely not.

Does it make my Type-A travel brain extremely happy?

Absolutely.

The bigger lesson for me has been that packing light doesn’t necessarily mean owning less luggage. It means being intentional about what goes inside it.

I still want to arrive in Italy with one carry-on roller and one personal item. I just don’t want preparing for that trip to make the three weeks before it chaotic.

So for now, Italy gets its suitcase in the corner. Gaylord gets another. Work travel gets packed and unpacked as needed.

And slowly, outfit by outfit, Italy is coming together.

Next Carry-On Edit: my favorite luggage & why