First, look at the weather, season, and climate for the non-basics items you might want to pack. We were going from beach (Nice) to mountains (Le Cagnard), to plains (Loire Valley), to oceanside (Nantes), all during a very hot, dry summer. No need for a raincoat or heavy shoes, likely no umbrella or more than a scarf for warmth. We would need swim clothes, a coverup for the beach, good walking shoes, light clothes that helped us not sweat, and hats. The few days it rained through our trip, we planned indoor activities, or our hotel lent us an umbrella one evening to walk to dinner. We felt we could always buy an umbrella if necessary, which it wasn’t. We also knew we’d have at least one “nice,” even “very nice” meal.

We both forgot our surf shoes, and regretted it in Nice’s very rocky beaches. Money solved that with a pair of cheap mesh shoes with velcro closures and hard rubber soles. Surf shoes were the only thing we regretted not bringing, and we used everything we did bring. (I always hate bringing things I don’t use.)

We pack for five days at a time, plus a set of clothes for travel day. For a nearly three week trip, this means we do laundry twice — as we build that into our plans. This is our only real secret. We use laundry strips at home, and bring some in a baggie. A tiny strip an go in a tub or sink for handwashing, a quarter-sized strip goes into a regular washer.

For me, then, the planning shifts to deciding what exactly might get packed. I like to start with the tricky but unavoidable items: the “dress up” clothes. Dress or blouse & skirt? The former has more limited wearability, but takes less room and is usually seen as nicer than just a skirt and blouse; the latter has more options over more days. Knowing the answer, I then look at shoes. I knew I needed sandals, and nice shoes, as well as my usual sneakers.

What I ended up packing was:

bathing suit
caftan (beach cover up)
shorts (2 pr, 1 TD)
culottes
dress
t shirt (to sleep in)
sleep shorts
3 blouses (1 TD)
1 long sleeve shirt (I use it for light cover on cool nights, and often carry on the plane in case it gets cold)
5 pr each undies (bras, panties, and socks)
open sandals
low heel slip-ons
sneakers (TD)
not pictured: a sun hat

16 (not counting undies) items in all, all of which fit in a suitcase, or got worn on my travel day (marked as TD). You can see it all in the picture above. We share a hanging toiletry bag (like this one), which often goes in my bag as well.

My backpack carries my laptop, mouse, and power cord; camera bag, kindle, travel docs and passport folder, mp3 player (old school baby!), power cords for all the devices, phone, journal, pens, water bottle, and a bag of dried fruit and nuts.

Compression cubes make packing this much a breeze. Shoes get stuffed with socks, then go into a drawstring bag to keep everything clean (it’s the black one in the bottom right). Undies all go into a small compression bag (upper right, on top of the toiletry bag (not seen). The larger pieces are divided between two large bags (left side). Minor items (a brush, makeup bag, etc.) snuggle in the spaces between. We use the laundry bag as a handy way to track when we need to get that task done, and carry a 2 gallon ziploc bag in case we end up with wet clothes and no time to properly dry them before packing

So, there you have it. Packing for almost three weeks and three different environments.

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.

J. and I are pretty proud of how minimally we pack for long trips. Keeping our baggage to a roll-on and a backpack means we do lots of planning, but then have very little to mess with on our trip. At this point our toiletries and gewgaws take up almost more space than our clothes!

As this post goes live, we are in Greece. This trip includes a day in Frankfurt and several in Paris, so we have some tricky bits to navigate: it’s not just all sun and sand, but also some city walking and dining.

Here’s how we do it.

The most important choice we make is to not worry about wearing the same clothes several times. I know that sounds basic, but when you can take one less pair of pants or shirts you can free up a lot of space. Relatedly, each trip we’ve taken has had special issues to take into account. (More on that later.)

The second choice we make is to wear only clothes that will go well together — no ‘one off’ outfits. Every top goes with all the bottoms, and vice versa. Even our shoes are very carefully chosen (and kept to a minimum!) to work with as many outfits as possible. A sub-choice of this one is that we choose to look as much like locals as possible. We don’t wear sneakers, or jogging suits, or branded/ themed t-shirts. In most of Europe, this meant that people presumed we were from the UK — a compliment! Our third strategy is to wear the heaviest items on the plane. The fourth decision is to use compression packing cubes. (That’s not a sneaky affiliate link, just a page in case you need an explanation.)

My luggage has:

• (2) blouses
• (2) sleeveless tops
• two dresses
• shorts
• pajama set (doubles as ‘at home’ shorts and t-shirt)
• 5ea panties and bras
• 5 pr socks (Smart Wool)
• bathing suit
• beach coverup
• swim shirt
• sandals
• (city)walking shoes
• makeup
• hanging toiletry kit
• compact umbrella
• sun hat
• cribbage board and cards

And my backpack has:

• travel books & maps
• kindle
• mp3 player
• onboard amenities kit (my own design: includes nasal spray, eye drops, moisturizer, chewing gum, comb, and deodorant)
• roll-up water bottle
• journal and pens

I’ll be wearing:

• long skirt
• blouse
• cardigan
• hiking shoes

My sneakers are the All out Blaze Aero from Merrell. With a body made of mesh (which helps air circulation) and a very sturdy bottom they are great for clambering over dusty hillsides. I won’t wear them in Paris — too touristy, but for Athens and elsewhere, they are perfect.

In Paris I’ll be wearing Merrell’s Dassie Slide. A little dressier, but with a low profile that keeps them walking friendly. Note the sturdy bottom (which will help protect me from cobblestones).  I can wear them with low cut, no slip socks from SmartWool and be comfortable all day.

My nice sandals are the Leisa Annual from Clarks. These are a new purchase and I love love love these sandals. Like all of Clarks’ shoes they are well made and comfortable.  I first wore them for our 2014 Italy trip and have been wearing them ever since. For this trip I bought a new pair.

Once the shoes are figured out, I find everything else falls into place as we just make a list of scenarios:

• dinner out
• around the house
• sightseeing (walking/ metro/ city)
• sightseeing (car/ country)
• ocean/ pool time
• sleeping
• traveling (plane, bus, and car)

Of course each of those scenarios doesn’t require entirely new clothes; quite the opposite. We pick clothes that overlap in as many ways as possible, factoring in the weather.  I’m planning on it being in the high low 80s to mid 80s during the days, dipping to the low 70s at night, which means I’ll want to be wearing dresses and skirts most of the time. The addition of nicer jewelry, my cardigan, and make up will turn my daytime dress into a dinner-worthy outfit. Paris might be chillier since we’ll be arriving there at the end of September, so I’ll use my travel outfit of the long skirt there.  Pool outfits are the swimsuit and a coverup, easy enough. Sightseeing will likely be the sleeveless tops with shorts or a dress. Nice enough to look good over a long lunch, but cool in the heat.

Everything will fit into a a carry on — we love love love our TravelPro Crew 22″ suitcase. It has a 2.5″ expansion zipper which means you can count on having space in suitcase for your return . . . as long as you check your bag. It’s also super sturdy. We got ours for our honeymoon in 2012 and they’ve done a lot of traveling since then. They still look good and the zippers are perfect.  Here’s a pic of a similar model (ours are teal, not purple):

We also have ‘personal’ carry ons which we try to use to maximum effect. Mine is a laptop backpack that I use everyday. It easily holds my camera and other electronics, as well as bottled water and a change of underclothes. (Let me tell you, being able to change your undies after a cross-ocean trip makes for a much better transition into the world.) My bag looks like this:

We are prepared for any meal: simple to five star. Any reasonable environment: sun, rain, cool, or hot. It’s true that if it pours (like it did in Rome!) we won’t do well, nor if it gets below 60* (I’ll be a bit cold if that happens, J. would be alright). But whether we are hiking around a dig, or sitting in a cafe in Paris, we will look appropriate.