Packing for 3 weeks, 2 countries, 4 cities and 1 ~cybersecurity blackout~...in a carry-on (?!)

I am proud of myself, ngl.

May 07, 2025

I’ve devoured a lot of packing guides in the past, few have really impacted my habits, aside for ONE I found on Substack this month that inspired this approach (linked below, of course!)

I mentioned this in my last letter, but I’m currently on a LONG trip to Portugal and Spain.

The agenda looks (or looked— I’m almost done!) a little something like this:

2 days in Ericeira, Portugal: looking at wedding venues in the morning, working East Coast hours through late night
3 days in Cascais, Portugal: lunch with my fiancé’s family, one rest day, then changing hotels for one more day of wedding venue tours and working East Coast hours through late night
Surprise “cybersecurity” blackout, which was really a day to remember… and maybe had nothing to do with cybersecurity at all? All I know is that it was a wild day, I’ve never used the word “rations” in my adult life until this day where I suddenly found myself lining up for them, and that for the better part of the day we were fully convinced that apparently Russia had cut the power grid to all of Europe. This is all to say: no running water, no cell service, no cash, and no power for a day.
4 days in Lagos, Portugal: long drive down to Faro, returning a rental car, Ubering backwards from Faro to Lagos, checking in to an Airbnb where we’re heads down working East Coast hours and taking a beat from the hustle and bustle for 4 more days
6 days in Lagos, Portugal: parting with my fiancé and switching Airbnbs to check in to a 6 day girl’s trip in Lagos with friends also going to the same wedding, working East Coast hours for two of those days
5 days in Sevilla, Spain: meeting back up with my fiancé, Ubering back to Faro, hopping on a 3 hour bus to Spain where we meet up with my family for a friend’s wedding weekend

If you checked out after the first sentence, I can’t blame you. It’s a kind of mind boggling and nonsensical itinerary.

It’s a lot of cities, a lot of moving lodging every few days, and a lot of really full days, essentially starting the “work day” in the early afternoon and working until late in the night. On the days we do this, the day feels almost like two days!

Now comes the true challenge:

I packed for this all… in a carry-on. Can you even believe it?
That decision was less about the ease of a flight and more about the ease of moving accommodations every few days.
Only in one Airbnb halfway through is there access to laundry, so there has to be enough optionality (and enough underwear) to last a week without doing the wash… while still fitting in a carryon.
There’s a lot of weather variance: wind, rain, blazing hot days, as well as breezy and chilly walks on the beach.

How I did it:

This guide by Angie Uh helped immensely. I stuck to one color palette (blues, browns, whites, reds) and focused on versatility instead of packing individual “cute outfits” or too many accessories. I find that when I do the latter, I overpack on stuff I don’t reach for and never seem to have enough of the stuff that is essential for traveling: clean white tees, comfortable pants that can lounge or go outside, layers for different weather.
I tried something new and rolled everything and arranged it in my packing cubes vs. folding it. It made a bigger difference than you’d ever think! Mainly, I can actually view what I have more quickly when I unzip a packing cube as opposed to having to rifle through folded layers that are all similar colors and shapes.
A bag within a bag. My plane carry-on was an old Madewell tote (similar) that was intended to be nothing more than a travel carry-on. Inside of it I tucked pouches and always carried a tote or purse for the real essentials. This made it a lot easier to move from accommodation to accommodation! If my carry-on was also my primary purse I for sure would have lost something every time I dumped it out out to use it for a trip to the beach or to town.
You already know I’m a Kindle evangelist, but having an infinite amount of books in a finite and compact case will honestly save your hide during something like, say, a blackout!

Sartorial saviors and most-worn MVPs:

My monogrammed J Crew Etienne shirt was one of your most clicked links this month— and one of my most worn clothing items of all time.
I reach for this Z Supply shirt over and over again because it bridges the gap between comfort and societally acceptable to wear outside categories.
A classic oversized navy cotton sweater, also via J Crew last summer. This one is pretty similar via Buck Mason, or try this boxier new version from J Crew.
My pointelle lounge pants! I’ve worn these (and the shorts version!) every single day, and they’re under $50.
A pair of red Havaianas that I have also worn daily, whether with a silk slip skirt (this white or this red) or my lounge or beachwear.
Sebago boat shoes with white detailing in the butteriest leather ever… as comfortable as a sneaker, but more polished and more at home in coastal Europe than the Vans I wore on the plane. (Sold out here, but in avail in suede here!)

Workhorses that you should bookmark for your next trip:

You know what I absolutely needed when we lost all power, cell service and running water in Western Europe for a day? These water wipes that worked out just fine in lieu of a shower. Do not sleep on these and several packages of antibacterial hand wipes! I have lots tucked away in different bags… and thank god I did.
Pouch for all of my cords that contains a plug converter and a portable charger. I didn’t own one of these until I was prepping for my solo trip to London and Edinburgh and now I find that I am grateful for it on the reg.
I invested in a cuter and roomier toiletry bag— this cute one in waffle that’s monogrammed with my initials, via Etsy or Abbode— and it makes me happy. I love this similar one by Kule and may get it for makeup, which right now lives in an upcycled leather pouch.
There are to be NO hair tools plugged in to the wall of an old European bathroom, it’s always safe to bet— instead I kinda just lean in to the whole vibe and go for windswept, beachy hair. This air drying mousse (decanted into a Cadence container) is my preferred method! It looks very natural and never crunchy.

New treasures:

The best part of packing light is making room to find a few thoughtfully chosen souvenirs along the way! Here are a few of the things I’ve fallen in love with so far…

Discussion about this post

Ready for more?