FYI. I’m still adding to this. Once this sentence is gone, it means I’m done. 
I’m going to separate this out into two categories: “student/cheap travel” and “regular travel”. Certain things may apply across the board, such as avoiding gypsies in Rome, but certain things will be very different depending on your travel approach so select the category that best fits. These tips will be in random order unless I decide at some point in the future to get totally anal and further categorize. (Likely.)
*The bulk of the travelling under my belt was in that first “student/cheap travel” category, but there is significantly more to be cautious about in that situation as well, so that’s where we’ll start. General Tips follow.
Student/Cheap Travel
Luggage. Easiest choice is a hiking backpack. (Wheel a rolling suitcase through an ancient cobblestone street in the rain as you run to catch a train at 5am and you’ll understand why I say that. Plus a backpack keeps your hands free.) Tons of varieties. I don’t care how many pockets and gadgets there are-comfort is the number one deciding factor and that is determined by gender. Think about it in this very rudimentary way: men are built to haul and carry stuff with their upper body, while women are built to carry extra people in their lower body. (If that offends you, just consider where a man’s center of gravity is versus a woman’s.) Men, be sure to get a pack relative to your height and I suggest one with an adjustable chest strap. Women, be sure to get one with a strap that fastens right above your hips, keeping the bulk of the weight on your hips and off your shoulders.
Daypack. You’ll probably want a daypack for your camera, wallet (use a money belt instead!), journal/sketchpad, water bottle, map/guidebook, and the extra breakfast rolls you swiped for lunch. Women: if you chose a purse you must either have one with a zipper or a lock otherwise you’re asking for someone to swipe stuff out of your open bag. Men: same rule applies for your man-purse. USE A MONEY BELT for your passport and large bills. Yes, I always carried my passport with me because my hostel locker was broken into in London once. Carrying a mini-backpack is fine but again I suggest using a lock since it’ll be on your back, out of your line of sight. Share with a friend & alternate carrying; the one NOT wearing keeps an eye on the pack at all times. Camera bags: wear on your FRONT, or your camera may get swiped. HONESTLY, I suggest carrying all bags on your front, even backpacks, like we did in the early 90′s. You look like a goober? At least you still have all your stuff! Peace of mind, baby.
Sleeping. Bring a sleep sack: either buy one or simply make one by folding a flat sheet in half. You have no idea if the bedsheets have been washed, who did god-knows-what in it before you got there, or if you’ll have to pay $$ for sheets. They’re also nice as a blanket when you’re sitting up on a train overnight. I bought a little “throwaway” pillow from IKEA for $0.99 that I now stuff in my bag wherever I travel: hard plane seats, sitting up on a train, etc. I also have a small fleece blanket that I seem to use all the time. Lock your belongings in a locker in a hostel, or sleep with your money belt. Cute pj’s are overrated – I slept in the same t-shirt and sweatpants every night for two weeks while backpacking. Bring a flashlight and battery-powered alarm clock (or cell phone).
Regular Travel
Luggage. I love love love my Samsonite suitcases with the all-direction swivel wheels. Get a bag in a crazy color; you can find them on sale AND you won’t have to scour the red and black bags for yours. Mine are periwinkle and my moms is burnt orange. Save space for souvenirs. Keep $1′s or $5′s readily available to tip baggage handlers OR keep a death grip on your bag. Especially in Mexico – they think they deserve a tip for touching your bag regardless of whether or not you wanted the help.
Daypack.You can be in the slummiest situation after the craziest travel ordeals, yet you feel almost human again after your use your bare minerals lipgloss and Bath & Body Works hand repair lotion. Okay, so it may be a different brand or item, but you probably know the one or two things that can transform you in a matter of seconds. Have those things on hand. If the hotel offers a safe with a key in the room, you can put your passport and spare bills inside for safe keeping. Just keep track of how much money you put in in case some of it walks off.
Sleeping. If you are like a few men i know who simply can’t sleep with light in the room, you’ll want to get a sleepmask. Don’t tell me it’s silly-looking… who’ll see you?! And whoever else you’re with does NOT want to hear you whine at 7am about the sun.
General Tips
Passport. Travelling outside the U.S.? Make a copy of your passport, put in your suitcase and also a copy in your travel buddies suitcase (if you are with someone else). It took ~4 hours for Pops to get a new passport when his was stolen in Spain simply because my mom had a copy of his. It would have taken days otherwise.
Moneys. I suggest taking cash, getting it there from a Universal ATM, exchanging at American Express, and/or taking a single credit card. Write down the 1-800 number from your cards and keep in your luggage in case your card is stolen. Be sure you let your CC company know BEFORE you leave which countries/cities you’ll be in and for how long otherwise they may diable your card. I found too many places would NOT accept traveler’s cheques, so I advise against them.
Clothing. If you don’t already know, I’m anti-dry-cleaning so most of my clothes pack and travel well. Most hotels have cleaning/pressing services, but I’d still prefer to bring items that don’t wrinkle. Don’t take your favorite things because they may get lost or destroyed. Pashmina’s are a favorite accessory of mine for multiple reasons: can be wrapped around shoulders for warmth, can be draped on a seat to lay down, can be draped over windows or bunks for privacy, can be wrapped around head, can be wrapped around your waist to hide panty-lines, missing belts, and the fact that your pants don’t match your shirt.
Must-Haves. pocket knife with corkscrew, mini-first-aid kit, ipod w extra set of headphones, cheap sunglasses, sunscreen, headband or headwrap, flip-flops. In my purse or day-pack, I keep: eyedrops, chapstick, hand sanitizer, gum, ibuprofen, little bottle of lotion. In the comfort of my own home I don’t use hand sanitizer but at the office surrounded by people breathing my air and using my keyboard, you betcha. You never know when you’ll be able to use a clean bathroom with soap again, so having hand sanitizer on hand is crucial. WOMEN: Also, keep some spare toilet paper/tissues/napkins on hand because many places either charge for TP or run out. and you know, when you gotta go, you gotta go. You can buy mini-rolls of travel toilet tissue, then simply re-fill as needed. Again, this is something you can use to barter with your friends. (LOL Okay maybe that’s mean. Just share the TP!)
Itinerary. Print the details of your agenda and map sections out to keep in your suitcase, then only carry around with you what you need each day. Trust me, carrying a Rick Steve’s book in hand as you wander ANY major city in the world is like a neon light screaming “Tourist” at every passerby. Plus, it’s just easier to have a map marked with spots and an itinerary than carrying around a thick heavy book.
Jet-lag, and the avoidance of. You can get jet lag from travelling to a timezone only one or two hours different than your own. One suggestion is to begin shifting your sleep pattern up to 10 days before by an hour a day. Go to bed one hour earlier than usual, wake up one hour earlier, then go to bed 2 hours earlier, and so on. If you don’t have the time or ability to do this, though, it’s okay. The best way I’ve found to avoid jet lag is just to skip it entirely. When you arrive at your destination, simply pick up where they are in the day. If it’s morning and you’ve been on a plane for 12 hours, get a cappucino and tough it out. You’ll be exhausted by the end of the day, but you’ll be on schedule. (I find this is easier than showing up in the evening and trying to force myself to sleep too early.) Usually, you’ll wake up the next day ready to go. Don’t take a nap unless you have to, it’ll just confuse your internal clock even more.
Suggestions for getting the most out of your trip. Talk to locals. If you are a bar-hopper or wine-drinker, ask them where they go. Ask them their favorite local place for food and what they eat there. Ask what the local drink is and then try it. It makes you seem like you genuinely want to experience a place, rather than just trample around taking pictures, and you’ll wind up at the best places having the best time, possibly making life-long friends in the process. (that bar in Cortona, Agua de Valencia, Icecream & custard-stuffed profiteroles, Capirosca Fragola, Spaten, and a bunch of “Mama’s especial” dishes stand out for me.)
