My strong suggestion would be to start paying attention to trends NOW - especially for flights. The more you know, the more you can jump on a good deal when you see it.
I'd also suggest flexibility - ie having a few places that interest you so when any one of them comes up as a good deal, jump on it.
Another thing is subscribing to various email alerts - whether flight price trackers or "best deals this week" sort of thing. I get regular ones from places like TravelZoo.
Also, don't discount taking a tour with a company. Folks like Gate 1 or Indus regularly have nice deals on really neat places. Those are ZERO stress vacations as the planning is done for you. Restrictive in some respects, but not as much as you might think.
And, of course, if the $$$ matter up front, create and stick to a "travel fund" where $XX out of every paycheck go into the fund, and let it save up on auto.