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This is a collaborative post. All opinions are my own.
My sister-in-law is a master at packing. She has five young kids, and managed to squeeze everything for her family's 10-day trip to Iceland into carry-on bags (including all their boots and cold weather gear). Meanwhile, Ben and I had two big rolling suitcases we checked plus car seats and a stroller. As we struggled to fit our big bags into our small rental car, it was pretty clear that their method was superior. Since then, whenever we travel--especially if we're flying--I try to keep our luggage compact. Traveling light is wonderfully easy at the airport, and you'll appreciate it again every time you have to deal with your luggage: loading up the trunk of the car, unloading into your hotel or vacation rental, etc. Especially now that we also have kids to carry, we can't be dragging around big oversized bags too!
1. Choose the perfect bag
The right bag is a critical component of packing light. So first things first, choose a suitable cabin bag (one that can fit in the overhead bin of any plane). There's a wide assortment of carry on luggage to choose from, including tote bags, satchels, wheeled luggage and more. One of the main factors to decide on is the material of the luggage itself. Do you want a hardside suitcase that will protect your fragile items, or a soft bag that can be compressed into a tight space? Do you want it to have wheels for easy maneuvering in the airport, or backpack straps so you can carry it hands-free? Personally, I think hardside luggage looks cuter and I like the ease of wheeling it around...but a big negative is that it can't be squished into awkward spaces in the trunk of your car. And if you end up bringing less stuff back home (like in our case, we ate a bunch of food and used up a bunch of diapers)...well, you can't exactly fold up a hardside suitcase and shove it into another bag.
2. Separate your essentials
Set aside the "essentials" that you want readily accessible during your flight and when you first arrive at your destination. This of course includes your boarding pass, passport, your itinerary, and printouts with confirmations of your accommodations and travel plans. It also includes cosmetics like contact lenses, a mini-toothpaste, makeup, and deodorant--whatever you'll want to have handy when you first arrive (make sure to adhere to the security restrictions for the amount of liquid you can carry). I also think it's a good idea to separate one change of clothes and underwear. Not only does this ensure you are prepared for any travel delays, but you'll also have a change of clothes easily accessible in case you get food spilled on your travel outfit. And you'll probably want your phone handy plus some kind of entertainment for the plane, like a magazine, headphones for watching a movie, or a guidebook to your destination. Pack all of these essentials in a separate compartment of your carry-on, so it's easy to find them.
3. Add your hard items
Next, set out all your "hard' items--the stuff that can't be squished down. This includes things like shoes, food, a laptop, diapers, baby wipes, waterbottles, and books. Try to limit the amount of these hard items that you bring, since they'll quickly fill up the space in your carry-on. I think two pairs of shoes is enough for most trips. And you can always buy diapers and wipes when you reach your destination, so you really only need enough to get you through your first day or two.
4. Compress all your clothes
Now comes the magic that makes this method possible. Put ALL your clothes into a compression sleeping bag sack. Now squiiiiiiiish them all down as tiny as you can. It's absolutely AMAZING how much space this saves. Yes, your clothes will get wrinkly, but honestly my clothes always get wrinkly when I pack them for a long trip anyways. Don't worry about making a separate bag for each person, you can put your whole family's clothes in one bag. When you reach your vacation rental or hotel, take all the clothes out and separate them by person. If you're staying in one place for the whole vacation, you could now put your clothes away in closets and dressers. If you're on a road trip where you'll be moving from destination to destination, then you can transfer them into separate bags for each person. This can be as simple as a plastic garbage bag each. You'll still want to limit the clothes you bring--if you'll be gone longer than a week, plan to do laundry at some point--but it's truly impressive how much space this one trick saves.
This is totally my sister-in-law's genius method, so I can't take any credit...but I can totally attest to its power! We watched them squish their family's clothes (SEVEN people, mind you) into one carry on bag.
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