We leave for Italy in nine days, and I have officially reached the stage of trip planning where I wake up thinking about something I forgot to put on a list.
Do we have enough adapters? Did I order the right shoes? Does everyone have something to wear to every wedding event? Where are the packing cubes? What will Arbor do on an eight-hour flight? And perhaps most importantly: how are we supposed to fit all of this stuff into our suitcases?
Planning a trip to Italy has been exciting for months, but now that we’re getting close, it suddenly feels very real. And scary. And maybe like it isn’t actually happening and I just dreamt all of this up.
For the record, this isn’t exactly a simple family vacation. We’re traveling to Italy for ten days with our three daughters and our Moms. We are visiting Rome, Lucca and Florence, taking trains between cities, and attending several events leading up to a family wedding. The wedding also happens to fall on my 41st birthday, which obviously makes this trip feel even more special than it already is.
So there are regular vacation outfits. Travel clothes. Comfortable walking shoes. Wedding looks. Rehearsal dinner dresses. Toiletries for the girls. Things for the plane. And approximately one million tiny things I am terrified of forgetting.
Here’s how I’m attempting to organize all of it.
I Started With Lists. So Many Lists.
I am a list person on a normal day, but apparently preparing five people for ten days in Italy requires an entirely new level of list-making.
Instead of making one giant packing list, I’ve been breaking everything down by person and by day. With three girls in completely different stages—one teenager, one ten-year-old and one four-year-old—there really isn’t a one-size-fits-all packing list.
I’ve been laying their clothes out on my bed, putting outfits together, taking pictures and making notes about what goes with what. I’m also trying to be realistic about what they’ll actually wear instead of packing fifteen “just in case” outfits for each child.
Although, ask me how that’s going when we’re actually closing the suitcases.
Planning Outfits Around Our Itinerary
This has probably been the biggest thing helping me stay organized.
Instead of thinking, What does everyone need for Italy? I’m looking at our itinerary and asking, What does everyone need for this particular day?
We have travel days, sightseeing days in Rome and Florence, time in Tuscany, a pizza party, pool party, wine tasting and lunch, rehearsal dinner, the wedding, a cooking class and more. That’s a LOT of different outfits.
I have bought a lot of clothing for the girls—especially Arbor. One would think the third girl would have plenty of hand-me-downs, and she did, but the good stuff has already been destroyed. Food stains, grass stains, weird stains—there is nothing she can’t ruin in one wear.
For months, I’ve stalked websites for sales and collected pieces that will work in Italy in September. Think warm days and cool nights. I’ve been laying everything out and assigning clothes to specific days or events. It makes it much easier to see what we’re missing—and what we definitely don’t need more of.
I Tried On Everything in My Closet
My own packing process has been slightly less organized. And by “slightly less organized,” I mean I’ve ordered and returned more items of clothing in the last four months than I have in the last four years. One half of my bedroom looks like a clothing store exploded in it.
I’ve spent weeks trying on different combinations, ordering things, returning things, rediscovering things I already own and standing in front of my mirror asking myself whether I will actually wear something in Italy.
One thing I’ve learned from traveling is that I don’t want to bring a suitcase full of individual outfits that can only be worn one way. I’m trying to pack pieces that I can mix and match—simple tanks, skirts, shorts, lightweight layers and comfortable shoes—and then add a few special pieces for our events.
And yes, I have been photographing outfits in the mirror as I try them on. It might not be glamorous, but being able to scroll through my phone and see the combinations I’ve already put together is surprisingly helpful.
The Luggage Has Been an Entire Situation
I truly did not anticipate spending this much time thinking about suitcases, especially when we already own a few.
We have checked bags, but we’re also moving around quite a bit once we arrive. We’re flying into Rome, traveling by train to Florence, heading to Lucca, returning to Florence and eventually going back to Rome.
Many people recommend we bring backpack-style luggage instead of dragging suitcases across Italian cobblestones. However, a backpack would never be able to hold everything we need. So while I want enough space for everything we need, I also don’t want to be the family dragging an unreasonable mountain of luggage through Italian train stations.
With five of us, there is also the question of who can realistically manage what. The older girls can help with their belongings, but Arbor is four. Naturally, she wants her own suitcase—which sounds adorable until you imagine navigating a train station with it.
This has involved far more luggage research than I’d like to admit, but I finally committed to two different sizes for the girls of the family (myself included). I wanted something lightweight enough that we can actually manage it while we’re moving between cities, but still big enough to hold ten days’ worth of clothes.
At this point, I am choosing to believe that everything will fit. Please don’t ask me again when we’re actually packing… I hope this weekend.
I’m Packing for the Plane Separately
One thing I don’t want to do is get on an overnight flight and realize that something we desperately need is buried inside a checked suitcase. SO our plane bags are getting their own lists.
I’m thinking about medications, chargers, headphones, snacks, activities for Arbor, entertainment for the older girls, a change of clothes, toothbrushes and anything we would really regret losing access to if our checked luggage were delayed.
I’m also trying not to overpack the carry-ons because whatever I pack for Arbor somehow becomes something I end up carrying. Funny how that works.
I’m Trying to Remember That Italy Has Stores
This is perhaps the most important thing I keep telling myself.
We are not traveling somewhere without toothpaste.
If I forget shampoo, we can buy shampoo. If someone needs another shirt, there are certainly worse places in the world to need to buy one. And if I somehow fail to anticipate every possible need my family could have over ten days, everyone will survive.
I want to be prepared because being organized helps me enjoy a trip once we’re there. But I also don’t want to spend the nine days before we leave so consumed by preparation that I forget how exciting this actually is.
The Final Week Before Italy
Right now, we’re in the stage where everything is slowly coming together.
There are clothes everywhere. Suitcases are appearing. Lists are being checked and rewritten. Packages are still arriving. I’m figuring out last-minute outfits, finishing things at work, keeping up with school schedules and trying to make sure our house isn’t complete chaos when we leave.
But underneath all of that preparation is a feeling I don’t want to lose sight of:
We’re going to Italy.
We’re taking our girls (and Moms!) somewhere we’ve talked about for so long. We’re going to eat pasta, wander through Rome, explore Tuscany and see Florence. We’re going to celebrate a wedding. I’m going to turn 41 in Italy surrounded by my family and friends.
The suitcases will eventually get packed.
And whatever I forget?
I’ll add it to the list of things I know for next time.
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