Pack less, way less
You really appreciate having less when you're racing across an airport or schlepping from train to train in a strange place. Traveling with a single carry-on bag is an art form well worth mastering. Don’t just figure, “Hey, the airlines let me check a bag, so I might as well do so.”
You can cure yourself of this habit the first time you walk off a plane with nothing but a carry-on and are on your way, while everyone else is milling around waiting. Next time you're at the airport, watch the people claiming their luggage. I certainly hope some of them are actually moving to the country at which they're arriving because you shouldn't need a bag the size and weight of a coffee table to get you through a vacation. Who looks oppressed and in pain? Giant Bag People. Who looks excited and adventurous? The ones walking past baggage claim on their way to the exit because they already have all their reasonable amount of stuff.
"Just in case” crowds out present opportunities
Traveling in the 21st century continually reminds us of how much we have in common with people in other places. I’ve been able to pop into a corner store for some forgotten item in cities from Nairobi to Nara to Newcastle. If that’s true while traveling most places on the globe, it’s even truer in your hometown. Quit hanging onto so much stuff “just in case.” Come on. You aren't on the moon! Let the excess go.
excerpts from Discardia: More Life, Less Stuff
I hope you're ready to try being happier traveling with less luggage. The best way to increase your confidence about lowering your load is to do this simple test at home before you travel. You may feel a little silly at moments doing it, but it can save you many more moments of discomfort on your trip.
Step One: Prepare Your Gear
Most of the places that bags and backpacks travel to are dirty, so spread something easy to wash on top of your bed before you begin packing (or especially later unpacking). Go through your itinerary pulling out and laying on the bed what you will need for each day. Layered clothing is your friend so double up to maximize your options wherever you can. And, when in doubt, leave it out. The odds of needing something you have to buy on the trip is vastly lower than the odds that you'll adore having light luggage every step of the way.
Joe and I travel with two bags each: a carry-on bag which fits in the overhead compartment (we like TravelPro Flightcrew) and an over the shoulder laptop bag or other day bag (I like the Timbuk2 Q backpack, Joe prefers a roll-top messenger bag from Mission Workshop). I also tuck a small, over-the-body-strap purse inside my day bag for lighter or dressy use.
While on the move, keep your day bag in constant sight. This is where you want to have all your valuables, including your passport, money, wallet, laptop, phone, and travel itinerary printout. You'll be keeping track of your suitcase too, but you want to be able to set it out of arm's reach, such as the luggage rack at the end of a train car or airport shuttle, without having to worry too much.
Along with valuables, your day bag is where you'll carry those things you want on the plane or other long rides. These include: snacks, reading material, earbuds, medicine, the quart size bag of liquids (such as shampoo, lotion, toothpaste, etc.) which airport security will want you to present as you pass through the security gates of most airports, and anything else small to keep you comfortable as you journey. Ideally, you should leave enough room in the top of the bag to tuck in your sweater if you get warm on the way.
Everything else goes in your suitcase, including nonliquid toiletries. Roll soft things like undershirts and underwear to create a dense, compact layer on which you can set items more prone to wrinkle. Don't forget to be sneaky with space-saving tricks like filling shoes with socks. Wear your bulkiest garments when practical; boots and thick sweaters are fine on your body but take up a lot of space in your bag. (Here's more detailed advice on packing light from Rick Steves and Heather Earl)
You should be able to comfortably lift your day bag and wear it without pain. It's okay if your suitcase is a little bit heavy but you must be able to lift it from the floor to waist-high racks or security conveyor belts and down again without hurting yourself. It's preferable if you can also lift it above your head to put it in the overhead compartment on a plane yourself, but in a pinch I find there is usually someone strong around who is happy to help if you apologize and ask nicely.
One last check: Turn your closed day bag completely upside down. Nothing should fall out. If it does, that's not the right bag to take lest casual losses or pickpockets ruin your good time.
Step Two: The Imaginary Airport
Now is where it feels a little silly, but stay with me; it's worth it. Couples and families should do this step together. Everyone should have a piece of paper and a pen to write down things they're learning in this step. This piece of paper also serves as your pretend boarding pass. No one should have anything that won't be traveling with them.
Wearing exactly what you'll be wearing when you set out on the trip, stash anything from your pockets in your day bag and note anything else which security may ask you to remove before passing through the x-ray such as belts with large metal buckles.
Now put on your day bag, lift the closed suitcase off the bed, and roll out of the bedroom(s) to form a line in front of another doorway.
Quickly retrieve your passport from your day bag. Show your pretend boarding pass and your passport to the doorway. Roll on to allow the next person to do the same and quickly put your passport away securely.
Return to the bed, which is now playing the part of the security x-ray conveyor belt. Put your suitcase and day bag on the bed, leaving space to between them for you to set the extra things you will need to show security. This varies from airport to airport and country to country, but often includes laptops, removed shoes, jackets, and permitted liquids in their quart bag. Here's how it works with TSA in the United States. Step back from the bed and confirm you can comfortably assume these two positions without your unbelted trousers falling down:
You probably won't need to assume that second position (for which I amusingly could only find that particular official TSA image) unless they need to do extra screening with a metal detector wand. It happens not infrequently and it's not a big deal, just relax and stay pleasant if it ever does.
Now you can step back to the bed, move your suitcase to the floor, and quickly return everything to your day bag. If your shoes aren't slip ons, it's polite to shoulder your day bag, pick up your shoes, and roll your suitcase over to one of the recombobulation benches to sit and put them back on out of the way.
Hooray! You're through security!
Roll on to your living room, set your day bags on your seat, lift your suitcases above your heads for a moment putting them in the imaginary overhead compartment, then set the suitcases aside and, standing awkwardly over your seat whilst pretending not to bump your head, remove your jacket before sitting down. Put your day bag laying flat right in front of your toes and breathe a sigh of relief. Now, without elbowing your seatmates, remove your reading material from your day bag and relax. Write down any notes you have so far.
Next, put away anything you've removed from your day bag, put your jacket back on (or stick it in the top of your day bag), and retrieve your suitcase again lifting it in the air briefly. Roll back to a doorway in a line, quickly remove your passport from your day bag and show it to the doorway before returning it to safekeeping and rolling on.
Now with all your gear, day bag still on, walk around rolling your suitcases for at least 10 minutes. Set a timer so you aren't tempted to cheat.
After this enlightening interlude—during which you will likely discover if your bags are too heavy—return to the bedroom and place all your gear on the bed.
Hooray! You're out of the airport!
Step 3: Venturing Out of Your Hotel
Now it's time to see how well your day bag works. Remove from the bag anything that you wouldn't be taking with you on a day trip including a stop at an internet cafe. Stash your passport in an inside pocket of your suitcase. Think about what the weather will be like at your destination and change clothes or add items to your day bag as appropriate. Now walk, take a bus, or if you need to drive somewhere nearby where you know there's a café or library with Wi-Fi.
Walk around for little while with your day bag on, stopping to adjust the straps or otherwise improve its comfort as needed.
Visit the café or library and use their Wi-Fi if you have your laptop or tablet, or a public Internet terminal if you don't, to check your email and send a test message. Being able to stay in touch is a great way to stay calm while you travel. Remember to log out of any accounts you logged into when you are all done.
Walk around a while longer, again testing the comfort of your day bag. Note any items which seem too heavy for everyday carrying and decide if you will leave them at home or keep them in your suitcase in future.
How do your feet feel? Are these the best shoes for this trip?
While you're out walking keep an eye open for interesting postcards of your hometown. These are ideal for writing thank you notes on your journey.
Congratulations! You've made your upcoming trip much better!