How do we do this? Well, we think through the whole trip and pack as little as possible to cover all the situations. We have bags that fit as carry-ons, namely I have an Under Armor duffel bag which is probably 8 years old and showing no signs of wear despite me using it for nearly every vacation and Mark has a "Cabin Max Metz backpack flight approved carry on bag" which is currently unavailable on Amazon.
|Mark's Cabin Max in the distance
|My UA duffel, topped with my hat that I didn't want crushed
Inside these we use packing cubes - you can get them in all sorts of sizes but the largest one I have tightly fits 6 rolled up t-shirts, a pair of shorts, a lightweight sweatshirt, and a set of pjs (shirt and pants). I probably could have fit another rolled up t-shirt.
Tip: pack the shorts, wear the jeans. Weather permitting, wear the sweatshirt too (but it was too warm and I was just bringing it as a habit from growing up in New England).
|Large packing cube, not fully packed
That's all in the largest of my packing cubes. In my midsize packing cube, I stuff my socks, underclothes, and also a knee wrap hoping if I bring it with me, I won't need it (that's how those things usually work).
|Large packing cube, left, with medium packing cube, right
I have a small packing cube but it mainly fits toiletries but since we were driving not flying, I didn't need to split up my toiletries so I didn't use my smallest cube. Here are my two cubes on top of my swimming suit and cover-ups in my duffel, topped by my hat.
|Starting to pack it in
Since we were renting a house and I didn't know what I'd need, I packed my hair drying and straightener in there (turns out I didn't use either of them as the house provided a wall hair dryer like in hotels and I didn't care enough to do any straightening)
|Packing cubes and such
My duffel has a handy end pocket used mainly for shoes, but I have a canvas pouch that I got from a Stitch Fix order that I use to bag my shoes, so I can use my shoe pouch for other things as well as shoes and not get everything dirty from whatever I've walked through. So in this end pocket I put a lot of liquids. As mentioned, we weren't flying, so I brought my full-size shampoo, conditioner, face wash, aloe spray, contact solution, and such. I put them in the end pocket because if they spill, they aren't near clothes.
Tip: wear the sneakers, pack the sandals.
Tip: bring travel size items to save on space.
|End pocket with liquids and my tan canvas shoe bag containing sandals
Next to this bag but not really in the picture is a small makeup bag - this contains chap stick, nail file, neutral eye shadows, and a few other things. I add my concealer since I haven't bought a second one to leave in there and my glasses wax because again I just have one of those, and this is good to go.
Tip: buy duplicates, in travel sizes, of toiletry items so you can leave them in your travel kit rather than remembering to raid your shower/bathroom before a trip. But this works best if you travel often otherwise you end up with a bag of expired goods.
Next up is my charger - I got the yellow coated wire from REI I think and it works well to corral cords for transit. I also got a thing to cover my charger cord to reinforce it and make it visually appealing. I usually stash this in the side pocket of my duffel so it is easy to reach and doesn't get tangled around anything.
|Charger ready for transport
|Fully packed bag, ready to zip
Note: those are not the ones we have, but the ones we have are out of stock (by The Chestnut on Amazon).
Tip: in a pinch, you can use these bags to vacuum pack your clean clothes to save on space but they may be a little wrinkly on the other side.
|Don't air your dirty laundry, vacuum pack it instead
We did bring several other bags of stuff for the house, like towels, sheets, beach items like an umbrella, games, sports equipment, food, and such. I didn't include those in this post since there's not much you can do to pack folded sheets, towels, and equipment more concisely - they basically are the size that they are.
I hope you found this post helpful!