Packing A Carry-On for Three Weeks

We’ve been traveling enough now that I feel like I can share some of the things we do to minimize what we bring, and even the longest trip doesn’t require more than a carry-on and backpack for each of us.

First: Most of your luggage will be made up of clothes, so our first strategy is, admittedly, kind of cheating: only pack for a week, and plan to do your laundry once a week. If you are in shared housing (such as airbnb or VRBO), just make sure there is a washer in your unit. If you’re staying in larger accommodations, like hotels, you may need to find a local laundromat and build in time to get it done. We’ve also had some success finding local services to come and get our laundry, returning it later that day. All of these options have different resource requirements — how much is hanging out in a laundromat worth to you in terms of lost travel time, or around your flat waiting for items to dry? We’ve tried both ways, and after hauling big bags through the cobbled streets of Paris one chilly December night years ago we vowed “never again.” Manageable luggage is worth it to us.

Once, we were staying in Edinburgh for a few days, and planned to do laundry there. Our flat had a washer so we thought it’d be no problem to get a couple of loads done our first night. Turns out there was no electric dryer, it was a rack AND it was pouring rain both days we were there. Our clothes took a full two days to dry, even when draped over the heaters the 2nd day. It was a big hassle and we barely left the flat trying to manage it. (Honestly, the rain was a big deterrent, too.) So learn from us: make sure there is a dryer, and be prepared for it to not be electric.

Second: Pack clothes that are versatile, lightweight, and easily layered. Every piece should be able to mix with others to make at least three outfits. You rarely need a new top every day, or different bottoms; to my mind you only need to change your underwear daily. The pictures of John on a trip to Italy are particularly funny since you can track the cycle of his three shirts. Still, nobody in Venice was going to see him 3 days later in Rome, so it was new to them! Even if you are traveling with a group, no one cares whether the same blouse comes out three times in a week. Avoid white clothes, they seem to be dirt magnets; opt instead for patterned or darker clothing.

My packing strategy starts with looking at the itinerary and listing what we’re doing. It’s mostly “go to museum” and “walk to dinner” but it’s the first opportunity for me to look for the unusual events. Like the special meal at a Michelin-starred restaurant, or the tromp through the woods truffle hunting. Then I make a list of different outfits needed. Finally, I lay out all of the clothing I want to take on my bed and build outfits.

Third: Packing cubes are your friend, especially the compression cubes. I prefer the smaller cubes, John likes the larger ones. You can fit about 30% more in your suitcase using cubes. (Hot tip: don’t take that as license to take more, instead think of it as room for souvenirs.)

Fourth: Build your outfits thoughtfully. This the heart and soul of being able to pack for three weeks in a carry-on.

Building outfits is when you need to be ruthless.

Here’s the most common outfit combinations:
Traveling (plane/ train/ car/ waiting areas)
Museums and general touristing
Sacred sites (many places require that shoulders and knees be covered; sometimes heads as well)
Cultural events (concerts, opera, plays, etc.)
“Dress Up” (such as a special occasion dinner, or a visit to Monaco’s casino)
Sleepwear
Beachwear
Winter(outer)wear
Outdoor (hiking, etc.)

I wear a specific kind of outfit on the plane, one based around looking pretty good while being comfortable. I usually try to nap on flights, and need to be prepared for delays; I also adhere to the philosophy that I’ll get better treatment from airport and airline staff if I present as looking like I’ve got my act together. Sometimes any little bit of an edge is crucial!

Travel clothes:
wide leg pants, stretchy leggings, or yoga pants
long-sleeve top (or lightweight sweater)
lightweight blouse, or patterned t-shirt
your heaviest footwear
comfy undies (this is not the time for a thong; and bring a change of undies if you’re flying overnight, you’ll feel so much better when you arrive)
scarf/ shawl
plan for layers in breathable fabrics
I avoid: any clothing that constricts waist, armpits, neckline, joints, or ankles; including skinny or tight jeans. Our bodies swell when we fly, so anything that you wouldn’t wear during a bad bloating incident is a bad idea when traveling. (If you don’t know what I mean by this, well “yahoo!” for your blessed life.)

To pack for a week, your travel clothes will also work for museums, sacred sites, and most cultural events. (Some people worry about being dressed well enough for cultural events. We’ve found that most places, especially during their tourist season, aren’t expecting fancy outfits. Being in a good pair of pants or a skirt with a nicer top is almost always nice enough to not get looked at. I usually bring one “dress up” outfit, which may be an actual dress or a skirt and blouse combo, depending on the place where are going.

Shoes are always a hard choice. What works for me are walking shoes (I’m currently in love with my Hokas), sandals (for warm weather), waterproof shoes (for cold weather), and maybe another pair of walking shoes in leather that can work for dressy occasions. In cold weather travel I just bring two pairs, because my clothes are so much bulkier and space is a premium. In which case my walking shoes will be waterproof and I bring a 2nd pair for dinner and nice occasions. (We take taxis to save my better footwear.) John long ago decided that he’d get used to walking shoes that present more nicely than sneakers; thanks to the prevalence of retail work that shoots for “business casual” employees, these shoes are actually very common. No, they will not be The Most Fancy(tm), but if that matters so much to you then I’ll hazard a guess that you’re not too concerned about minimalist packing.

For a three-week trip we took to Italy in September a few years ago, I packed:
knee-length dress (red, patterned)
2 pr shorts (black, Bermuda style)
2 pr yoga pants (black, wide leg)
4 tops (all different patterns, v-neck, squarish shape)
1 long-sleeved top (black with a subtle pattern on the arms for interest)
1 lightweight cardigan (black)
1 skirt (knee-length, black)
pajamas (shorts and short-sleeve top, made of woven bamboo)
straw hat
wool-silk blend shawl (lightweight)
leather sandals
leather walking shoes
sneakers
swimsuit
undies (7pr)
socks (4 pr — I used Smartwool socks)
cross-body purse
toiletries
tiny umbrella
three-quarter length microfiber coat

(I wore a lot of black back then. There’d be a lot more blue in the list if I were to go now.)

All of my clothes (except where noted) were made of a mix of rayon and either tencel or nylon, from J Jill’s “Wearever” collection. I don’t own “travel clothes” that I don’t wear in everyday life. I bought a pair of flip flops when we got to the ‘beach’ portion of our trip (we had a car, so they lived there when I wasn’t using them). I carried the coat on board the plane.

If I went on that same trip in the height of winter, I’d drop the swimsuit, shorts, and sandals. I’d add a sweater. I’d replace the lightweight cardigan with a heavier version and the skirt with a calf-length version. My coat has a Thinsulate lining, so if I add gloves and a hat I’ll be toasty warm wherever I go. Note that even though European airlines have different requirements, everything on my list will fit in the smaller size most airlines require.