Step 1: You will not be checking a bag. Pick your luggage accordingly.
I travel with two bags: a suitcase-type thing and a messenger bag. The messenger bag will carry anything you want immediate access to (it will live by your feet, whether you’re on a plane, train, bus, or car), things like your wallet, phone, iPod, and snacks (see Step 6). Everybody knows how to pack that stuff, because it’s the stuff you have anytime you leave the house, so here I’m going to focus on instructions for the suitcase-type thing.
I love a good backpack. It frees up your hands to do whatever your hands need to do (hail a cab, pay a bus fare, fight off pirates) and it won’t get hung up on curbs or cobblestones like a rollerbag. Plus, by its very nature, a backpack has to be something you can lift, and I am proud of both literally and metaphorically never having baggage I can’t carry around on my own. Maybe for whatever reason you prefer a rollerbag or a little overnight bag or what-have-you. That’s your call. Just make sure that it’s stowable in the overhead compartment or under the seat in front of you, because the last thing you want is a suitcase you have to pick up at baggage claim or, worse yet, one that they can lose for you. If you’re not flying, you have more leeway with this, but keep in mind things like, How much room do we have in the trunk? How many friends am I riding with? Be considerate of the space. You don’t need that much stuff.
Step 2: Do not fill your bag all the way up.
Think of everything you’re going to need for the trip. Hold on—you’ve already thought of too much. I’ll say it again: You don’t need that much stuff. Really, you need very little. Underwear, for example. Deodorant. Prescription medicines. These things are important.
But remember, you will almost certainly be bringing things back from your trip. I never plan to get souvenirs, because I think that the photos and memories are enough and because I’ve already paid quite a lot to get wherever I’m going and have a roof over my head and eat food and so on. But then I always wind up buying things, little gifts for friends or mementos to sit on the shelf for me to stare at when I ponder the purpose of my life. So remember to leave room now for the stuff you’ll acquire along the way. Shipping things is expensive!
Step 3: OK, now you can pack.
Pack for the trip you’re taking. Are you going camping in the mountains? Then don’t forget your hiking boots, but you probably don’t need jewelry or makeup, because the bears will not appreciate your fine accessories. Going to the beach? Then swimsuit, yes; business suit, no. The tendency is to bring too much so you can be prepared, but if you know yourself, know what you like wearing and feel comfortable in, and know what you’ve got planned, you can look at your closet with clear eyes and say, Sparkly blue miniskirt, you will not be needed at the family reunion in Wolverville Falls, Michigan, pop. 300.
Step 4: Now take stuff out.
Do you really need three pairs of shoes for one weekend in Portland? No. They do not care that much about your feet. One pair of shoes comfy enough for city and trail walking will do you just fine. Those cute heels to wear to a theoretical nice dinner? Are you sure you’re going to a nice dinner at a place that requires cute heels? No. Will you just wind up at an awesome food cart instead? Yes.
Likewise, you don’t need more than one skirt or jacket or pair of jeans. If you think you need multiples of something, think, couldn’t I just wear the first one again? Yes, you could. And should. No one knows you where you’re going, so no one will notice if you repeat the same nice dress for dinner three nights in a row.
Step 5: Now add all the things you forgot.
Hair brush (I forget this on half the trips I go on). Bandaids (always useful). Chargers for camera/phone/iPod.
Step 6: Snacks!
You weren’t seriously going to go on a trip without snacks, were you? No matter how you’re travelling, you need to bring snacks. It will be way cheaper and healthier than buying it at an airport or gas station. Ideally, a snack should include something salty, something sweet, and something protein-y. My go-tos are almonds and craisins, but any kind of trail mix, peanut-butter crackers, beef jerky, licorice, etc., that you like should do fine. It should be nonperishable, obviously, and not melty (chocolate- or yogurt-covered things aren’t ideal).
Step 7: Double-check your documents.
Have stuff printed out. I know, you can get it all on your fancy phone. But paper works even when you’ve got no bars or your battery’s dead or your phone got snatched on the bus. At a minimum, have your ticket confirmations/boarding passes, reservations for hotels and any tours or restaurants, especially things you’ve prepaid for (and make sure it says “prepaid” somewhere on your piece of paper), and a map with the directions from your place of arrival to wherever you’re staying that night. Bonus tip: If you’re travelling in a country where you don’t speak the language, make sure to have the address of where you’re staying written out in the local language. When you arrive in Antwerp in the middle of the night dying of the flu, this will make it really easy for a taxi driver to take you directly to the softest bed you’ve ever slept in.
Step 8: If you forget something, no problem.
The only thing you can’t buy on the road is an ID—and if you find the right spot, you might even be able to get one of those too. So don’t worry. Just go.