We’re checked in for our flights to Rome, our two carry-ons are packed, and the Lyft is scheduled for 4:45am tomorrow. As usual, I feel like I should have prepared more: learned some Italian phrases with the kids, checked out playful library books about the Colosseum, fleshed out all the day trips and dinner reservations. I’m someone who needs a hard deadline.
Ready or not, we’ll meet my in-laws in the Italian capital for a week before we all head to the Tuscan town of Lucca for the second half of our trip. When it comes to traveling with little kids, I insist on sticking to one or two bases.
How it went down: Over two weeks have passed, and we’re now back from the big trip. I planned to publish this before we left but ran out of time. That means I can insert reports on how the packing actually worked out.
I avoid checking bags because anxiously scanning a baggage carousel isn’t a fun way to start or end a trip, and a missing bag can make a dent in the whole experience. It also helps that my low-maintenance husband sacrifices nearly half his suitcase for our kids’ clothes.
How it went down: The joke was on me. We immediately had to check our carry-ons at the airport check-in counter. Turns out Air Canada enforces strict luggage dimension limits, and our hard-working Away Bigger Carry-Ons (which we recently carried on a Delta flight to Europe) didn’t make the cut. But in all seriousness, we were grateful to only have two small suitcases when we were dragging them a half-mile on cobblestone sidewalks to our rental apartment or navigating train station stairs.
I don’t claim to be a master at minimalist packing, but as we gear up for our fourth transatlantic trip with kids (in addition to dozens of domestic flights), I can share my approach to traveling light-ish as a family.
For starters, I made sure both the apartments I booked have washers. (Dryers aren’t really a thing in Italy — all those postcard images with hanging laundry are accurate.) We’ll likely do a load of laundry in a tiny European-sized washing machine every couple of days, given that my kids love an outfit change.
Below I’ve outlined everything I packed for my two girls, who just turned 3 and 6, as well as the outfits I’ve planned for myself. Our suitcases are full but not stuffed, in case we’re blessed by the shopping gods.
How it went down: I did in fact make several “made in Italy” purchases, including a pair of shoes, a small straw bag, a thrifted scarf and button-down, and a heavy Santa Maria Novella candle, all of which I was able to cram in for the trip home.
Each girl gets her own packing cube filled with the following:*
3-4 dresses
3 bottoms
3 tops
2 nightgowns
6 socks
6 undies
2 pairs of shoes (in case one pair gets wet)
1 swimsuit
1 hat
*This list includes the outfit worn to the airport
How it went down: Despite going through multiple changes each day, I still could have gotten away with packing two fewer outfits for each child. They just wanted to wear the same things on repeat.
The kids will also each carry a backpack on the plane containing:
water bottle
extra outfit (from the above list)
pajamas (ditto, worn on the overnight flight)
toothbrush (fun parenting challenge: bedtime routine in an airport bathroom)
new sticker books and dry-erase activity books (from our favorite neighborhood bookstore)
coloring book with mini pack of crayons (latter saved from restaurants)
Yoto player, cards, and headphones (for the plane and long car and train rides)
small blanket and/or stuffed animal
How it went down: Little did I know that my oldest took her Yoto out of her backpack for a quick listen the morning we left and added several additional plush animals.
I’m thrilled to announce that we’re going car-seat free. Instead I’ve packed an inflatable booster for the 6-year-old and a borrowed RideSafer Travel Vest for the 3-year-old. I decided to leave our plane seat extender behind.
How it went down: Traveling without car seats was a game changer, but keeping the girls upright and properly strapped into their new containers required extra vigilance. At one point during the long drive to northern Tuscany I had to sit between them in the backseat.
For the past couple of years, I’ve been working with a brilliant style educator, Conni Jespersen of Art in the Find, who’s helped me develop stronger outfit-building and shopping skills based on my moodboards and gap lists. She helped me pack for my last big trip, so this was my first chance to try out what we practiced on my own.
Since the daytime temperatures in Italy are expected to be in the 80s and 90s, I didn’t have to worry about squeezing in bulkier layers. I call this packing in easy mode.
Here’s all the clothing that made it in my suitcase:
Bottoms
2 skirts (midi and maxi)
2 shorts (trouser and pull-on)
1 lightweight cropped pant
1 dress
Tops
5 sleeveless tops (with texture or detail)
1 white base tank (pairs with any bottom)
1 cardigan
Shoes
1 ultra-minimal sandal
1 flat
1 sneaker
1 heeled sandal
Other
4 small, soft bags (leopard, green, brown, red)
2 hats (ball cap and sunhat)
1 swimsuit
2 pajamas
How it went down: I was quite happy with my clothing selection, but I ended up only wearing the ball cap once — turns out they’re more of a thing in California than Italy. Also, I didn’t wear the brown bag because early in the trip I purchased a little handmade straw pouch that worked better with my summer outfits.
I’d also have packed my black silk skirt and a clutch if I’d known I’d get my daughter and me tickets for the ballet at the Teatro dell’Opera di Roma, where everyone was dressed to the nines.
My personal item for the plane is a small duffel with essentials (water bottle, sleep mask, glasses, foot hammock, earbuds, toiletries, adapter, charger, extra outfit, novel). On our trip to Germany last year, we were required to check our carry-ons, which were subsequently lost for three days. We arrived in Munich without any clothing, toiletries, diapers, or a stroller, and no stores were open during the long holiday weekend. Now I make sure we all have a change of clothes and toiletries in our personal item bag that we’re guaranteed to bring the plane.
When it came to packing for myself, I started by hanging out all the pieces of clothing I thought I might want to bring on a small clothing rack. From there, I made three outfits with each bottom (or dress) and put away anything I didn’t use.
I came up with some casual and dressier ways to wear a swingy denim mini dress, starting with a chic daytime look.
I can see myself wearing a sportier getup for a long day of sightseeing in Rome.
I tweaked the accessories and added heels for a dinner look.
Who knew an airy a-line skirt in a wild color would be a star of my 2026 summer wardrobe? I wore this easy outfit in Croatia last month and plan to repeat it.
I’ll also be repeating a combo I wore to host my daughter’s recent birthday party.
I mixed in a textured top and heels for a potential evening update.
I wore this gingham skirt a ton last summer and feel like it needs to see Italy, maybe because it reminds me of a tablecloth at an old-school, Italian-American restaurant.
One thing I love about travel is that you don’t have to worry about over-wearing your hard-to-forget pieces because no one has seen them yet.
I also like the way a tailored vest balances the flowy skirt.
I swore off shorts after the teenage hell of squeezing my thighs into clearance-rack Abercrombie cut-offs, but a few years ago, I discovered that I love a trouser short with a loose, mid-thigh cut, like this linen pair. I appreciate how a romantic top softens the look, keeping it out of preppy territory.
Ruffles can feel overwhelming on my short body, but the hat somehow helps balance things.
I surprised myself by how much I appreciated this evening look with shorts. How it went down: I only got a couple of wears out of the vest on the trip because I didn’t trust the unfamiliar washers not to shrink it and never got around to a quick hand wash.
These drawstring gingham shorts are basically extra-flattering pajamas. I feel a little like a Disney mom when I wear sneakers with shorts, but sometimes that’s just what works.
How it went down: On trips to Mexico, I’ve noticed that few local women wear shorts, no matter the heat, so I was relieved to see that they aren’t a fashion faux pas in Italy.
Sandwiching a contrasting outfit with a color-coordinating top and shoe adds polish.
Some question my commitment to white pants as a mother of two young kids, but what can I say, I’ve been drawn to them since I was a teen and feel totally myself when I’m wearing a pair.
A linen or cotton pant is my warm weather go-to in San Diego, so it’s interesting that I didn’t lean on them more here.
The pants will come in handy for the air-conditioned airports and planes.
While I made tweaks to some of the outfits depending on the exact circumstances of the travel day, having an album of options to refer to when getting dressed created a sense of ease and confidence. I felt comfortable and put together while exploring cities and towns packed with some of the most stylish residents and visitors I’ve come across. Trying on a bunch of clothes in the final manic hours of trip planning took up precious time and headspace, but I have no regrets. When I love my outfit, I’m just an altogether more pleasant and patient traveler.
Up next week: A full report on our multi-generational trip to Europe, including lessons from all our mistakes, plus copious local style notes.
Do you plan your outfits when you pack or just throw things in your bag?
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