Honestly, one of the biggest keys to a good backpacking trip is starting with a good backpack. Go figure. Forget the designer luggage, forget the rollerbags, forget the footlockers- you’re going to be BACKPACKING. Get a backpack...
To get started, visit your local camping surplus or outdoor/adventure store, get some help from a ‘professional’, and try a few ‘Expedition’-sized packs out. You’ll want something sturdy, something durable (internal frame packs are best), and you’ll want to make sure it ‘fits’- all backpacks are different. When trying a few on, make sure you load them up with about the same weight you envision traveling with- that way, you will get a better feel for how the pack sits when loaded up. Pay attention to how the shoulder, hip, and chest straps feel- you’ll want them to be sturdy, but comfortable. Also, check the various compartments and inner chambers- more compartments means better organization, but too many dividers means smaller packing spaces. Front-loading packs (Ones that can zip open in the front) are easier to pack/unpack than top-loading packs. After you’ve gotten a good idea about what you need, check around online for pricing- often, you’ll find the exact same backpack online for much cheaper than you would’ve paid for it in the store.
A few other things to think about:
You’ll want to make sure to get a rain cover for your backpack- a waterproof sheet that easily slips over the outside of your pack to keep it and it’s contents dry during inclement weather. These are usually pretty cheap, and fold up into a small carrying pouch. Worth the investment, for sure.
When shopping for your backpack, check around for a large ‘duffle-style’ bag that you can zip your backpack up into- this will prove invaluable when checking your backpack in on flights, trains, boats, etc. Putting the pack into a duffel bag ensures it won’t be damaged by straps and/or clips getting caught in conveyor belts and/or transport machinery when out of your care. Also, having the duffle will allow you to lock up your bag* anywhere and everywhere it isn’t actually on your back. Airplanes, hostel dorms, overnight trains, hotel luggage rooms- having your backpack inside a lockable duffle keeps it cleaner, and provides an added layer of protection against theft. Honestly, if someone REALLY wants to get into your stuff, they’re going to, regardless of what it is packed in, but having that extra layer of deterrent may make a potential thief think twice.
While checking out large backpacks, look for some smaller draw-string bags to pack your gear in within your larger pack. Get a few, each a different color- i.e. a blue one for shirts, a grey one for shorts/pants, a red one one for socks/underwear/swimmers/etc.- this will help you stay organized while on the road, preventing episodes of having to throw everything out of your backpack in order to find that one shirt or those elusive swimmers.
You will also want to keep your eye open for a good daypack- a smaller backpack large enough to hold a day or two’s worth of clothing and other essentials. This daypack will prove invaluable when going on long hikes, overnight excursions, and any other times when carrying your large backpack is impractical.
*TSA approved locks, of course... Try to get small combo locks to avoid having to keep up with keys.