I. Forget the Planning:
Instead of making sure that you're packed and planned for three months in advance for a week away, do it the night before. It might sound like an incredibly bad idea; packing the night before, however, makes life more interesting and it's that element of risk that adds to the feeling of elation that you get when going away.
Just make sure you have your tickets, passport, etc before the last minute. Worrying about that sort of thing makes for panic, as opposed to hurry; the latter is more fun, the former an accident waiting to happen (last time I panicked before travelling I managed to leave hair straighteners on, on the bed, and burnt the duvet: not fun).
II. Travel with Friends, Not Family:
Unless your family don't burst into argument over dinner on at least a once weekly basis and enjoy the same activities as you it's probably a good plan to avoid going on holiday with them if you can. Basically, if you're old enough to travel alone then give it a shot and see how much more fun it is when you're doing what you want and, if not what you want, then something you can enjoy with friends.
I've been travelling by myself since I was fourteen and with friends since a year after that, it's much more interesting when you can go where you want and do as you will, rather than get stuck somewhere less fun than in front of your PC.
III. Absorb Foreign Culture Instead of Planting Yours:
“Travel” and “holiday” are not synonymous. Travel is often what comes prior to the holiday, or maybe the entire holiday will be spent moving around; either way it can be an experience rather than a requirement.
Cutting to the point, when travelling in order to enjoy a place, it's hypocritical to go somewhere because it's different to your own home (sunnier/more interesting/busier/quieter/etc) and persist in treating it like that home. If you go to Africa, go visit something that you don't have at home, by all means, but keep it interesting by doing those things in a different way. If you go to the Mediterranean and want an interesting experience then don't lock yourself away in a compound full of people of your own cultural background, surrounded by little houses built by people of that culture for their own.
IV. Make It Interesting - Be Interesting!
Be interesting yourself. Don't expect a different place and its people to be interesting just because they're not the same as at home. Places and people differ, but on the other side of the coin they also share a lot of traits. Therefore the people on the train don't talk to you because you don't talk to them; the man at the foreign restaurant does not make an effort to speak your language, not because he doesn't speak any of it, but because you didn't go to an effort to learn his; the pictures you take look like boring holiday photos because you took them like that.
So be responsible to yourself and make an effort to actually be interesting to both yourself and other people, it's hardly hard to do it and have fun. You actually have more fun when you feel as fascinating as the place you're going and you make life more interesting and better for other travellers and the natives.
