I'm one of those people that doesn't plan ahead well to get away. Nor do I do it enough, which was a whole other issue.
I think I'm getting the hang of it though. Here's my thoughts in case they help others.
1. separate travel fund. Not much but enough for a long weekend getaway. It's always waiting for me, even if I don't plan.
2. strategic use of airline rewards. I use the card for almost everything so I always have a flight waiting for me.
3. paying attention lol. So far I've taken 1 and have 2 booked with almost no cost for flights (Caribbean and Mexico, 1, 2, and 3 passengers respectively). I match up flights that use few points with sale or cheap stay options. Even a trip for me and the kids during spring break despite those inflated prices!
4. looking more for low cost things locals do. And then having that budget room for something more expensive but special or important to me.
Bon voyage : )