When to go?
I went to Europe, so I can only speak to the European timeline. If you have money, you can probably wait until spring, when it will be warm and people will be having spring festivals. If you're heading out there with your last four paychecks from aforementioned shit upon job and some prayer, I suggest leaving in November-ish. You'll be there for the winter holidays, which is fascinating, you'll have your pick of hostel beds, and while you'll freeze your ass off, you have an extra layer of protection against pickpockets if you wear a money belt/lanyard and zip up your overcoat. And shit will be cheaper apart from holiday time. Also you can find some wayward Americans to celebrate Thanksgiving with!
Where to go?
Examine your options. Do you have family or friends anywhere in a different country/continent? Work 'em in. Are you interested in any particular area? Do you speak any particular language? Work those factors in and you'll find yourself enjoying yourself more, and if you speak the languages, you'll be more able to pick up casual employment. Also for Europe: further east you go, the cheaper it is. Keep that in mind.
Do what I say, not what I do. I ended up in Eastern Europe because my girlfriend got a nice scholarship package to study in Slovenia. I was only dimly area of the history of Yugoslavia and always associated Serbia with Slytherins for some weird reason. It all works out.
How Do I Get Around?
1) Pick an area and stick to it. Flying is expensive, so if you're planning on switching regions, book in advance and EasyJet/regional cheapairline it if possible. You'll see more, get a more coherent sense of cultures/areas/languages and be a lot less light in the pocket if you minimize flights and stick to trains, automobiles, and bikes.
1.A) Some people hitchhike. I don't. Some people do long distance buses full of farm animals. Again, I don't. While hitching is close to free and buses are cheaper, know yourself and your preferences. I'd prefer to spend an extra 15 dollars and an extra two hours and take a train. They're more comfortable and I get horribly motion sick in busses. Plus, I have an excellent array of train bathroom photos now!
1.B) Ask at your hostel or local places if people have any tips about getting to the neighboring country. Someone may be going there and I classify friends of friends as Not Hitchhiking, and at the very least they'll have some tricks to minimize cost. Getting from the Czech Republic to Poland was ridiculous, but a 5 Minute Friend at a cafe gave us the times of a commuter train to a town near the Polish border and advised us to take a bus to a town in Poland, and then hop on a train from there. Easily fifty Euros cheaper.
Traveling while Backpacking is like the episode of The L Word where we learn about the Triangle- you can't have something good, cheap and quickly, you can only have two of those factors at once. Pick your two factors. Hint: cheap will always be one.
Where to Stay
1) Couchsurfing is great! You meet local people, see local things, and have more of an opportunity to blend in and be less tourist-y, getting a short version of "ReaL Life" in a location. Always screen your Hosts carefully. Some people Couchsurf alone...I don't, but again, its all up to you and your comfort level.
2) Now, on to hostels. Hostelbooker and Hostelworld, I use both, whichever is having a better price is the one I book at. Read reviews on both. Try to find the cheapest one that includes breakfast- you can hoard enough food for lunch, usually. If reviews mention bugs or vermin, keep away. I found that anywhere rated below 60% was usually absolutely intolerable. At one point I payed five American dollars to stay in a newly renovated but Not Officially Open dorm that lacked heat, running water and a floor in some areas. After that, my girlfriend started choosing the hostels.
2.5) Hostel location and culture. Be sensible when looking at location- if you're getting in super late, try to pick somewhere nearby, if you're only going to be somewhere for 24 hours, don't pick a hostel out in the suburbs that will eat all your commute time. Do you want to party and is it safe to party where you're going? Try to book a hostel that caters to that, so that you can make friends to go out with, and so that people won't want to steal your shit and pee in your bed when you come in at five am plastered and screaming "viva la germany!" into a hostel known to cater to families and traveling workers.
2.8) Check for bedbugs: hit the mattress and watch, or hold a lighter near the bed frame and see if anything jumps out. If there's obvious vermin I'm out, but even that can negotiable in desperate times. But bedbugs, fleas, and lice are not negotiable, and honestly those tend to come anywhere there's obvious vermin.
What Do I Bring?
As little as humanly possible. I brought very minimal clothing, my Kindle, a small camera, a towel (get a dry quick one and you'll love the universe!), and the usual toothbrush/paste and hairbrush/hairties. Bring the makings of a first aid kid because if you don't, you will find yourself in desperate need of one.
Remember, you're carting this shit around on your back. The less the better, but don't forgo a few little things that will make you comfortable, either (Kindle, journal, beads). But don't bring a laptop! You can find an internet cafe or a hostel computer almost everywhere and seriously, its like asking to get it stolen, its heavier than everything else you own, and just,don't.
Clothing should be practical, come in layers, and incorporate sensible shoes. I wore boots for 3+ months straight- my feet were never wet or cold, though I admit to some smell-age. I'd avoid sneakers just because I never saw anyone wearing them until I got REALLY far east in Europe and I feel like its very American to wear sneakers everywhere. Be culturally sensitive- even when you don't agree or think the standards are bullshit, you're outnumbered and a guest in their country/region/culture.
Also, know what activities you're going to do- I'm really interested in mosques so I brought a cheap hijab I picked up since the communal hijabs for tourists were freaking me out, lice much? If you're a rafter or going sailing or swimming or rock climbing, you know the gear you should bring.
Your backpack should weigh less than fifteen pounds if you don't want to hate yourself/give away your belongings in a fit of back pain.
Safety
You're probably a smart cookie, but here's the inevitable safety reminders I'd feel guilty not giving you, plus some backpack-y ones.
1) Always have someone who knows your vague route. Make promises about when to check in with family and friends, and keep those promises. Register with your country's embassy wherever you're going and know the vague location of the nearest embassy.
2) Don't do drugs or drink until you make bad decisions. You don't know the laws and what might be a fine or probation in the US could be prison time where you're going.
3) Be a good traveler. Keep an eye on your shit, be polite and culturally sensitive.
3.5) Don't wear expensive jewelry and clothing or flash expensive electronics. Common sense stuff.
4) Be safe sexually. If this is a concern for you, make sure to bring birth control for your entire journey (availability may vary where you're going!) and barrier devices so you don't end up trying to figure out the citizenship of a canadian-serbian baby born in guatemala.
5) Know what your health insurance will cover if you break an arm, get an ear infection, need a medical evac to another country, etc. Will they reimburse you for emergencies? Are you covered for evacuations?
6) I never even thought about landmines, then I went to Eastern Europe. Know safety for hazards in the area. (Don't step off the pavement in Sarajevo!)
7) Get away from the border. Seriously, its not a cool place to hang out, shit goes down at borders. Get your stamp and move along. Nothing good ever happens there. Oh, and make sure you get a stamp or whatever the entry procedure is. I almost illegally entered Serbia because my passport got tossed around to so many officials that by the time it was decided I was okay to enter, everyone had forgotten to stamp it. Awkz.
8) If someone is screaming at you and they have an AKA 47, apologize profusely, do not move, keep your hands visible, and say Embassy as clearly as possible.
I cannot put enough emphasis on the last one!
Have fun!
