I like to go on vacation annually and put away $600 a month and usually end up doing one week long trip in the $5000 / $6000 range for our family of three and a get-a-way weekend (often that get-a-way weekend is an Orlando trip that isn't too expensive using frequent flyer mile, staying offsite, and short (often only there for two or three days)). And DH doesn't like theme parks so it's usually just me and DS.
If a trip is going to cost more than $8000 then (over 13 month's of vacation budget ($7800) It would have to be something we really really want to do and would be willing to make some sacrifices for (more modest vacation next or less frequent vacations) or I'll start coming up with a different place instead. // e.g I was looking at an Alaskan cruise for the three of us (balcony was all I'd consider) and it was sooo expensive. And I said -- no way -- I don't want to go that badly - it's not a bucket list item or anything like that -- was just a vacation thought. And instead we decided to do our favorite National Park -- a trip to Estes Park / Rocky Mountain National park in style with a wonderful luxury condo with hot tub on balcony and fabulous view, fly and rent car to save about 26 hours of driving, and $6000 will easily cover the whole thing. Can't wait to hit that park again (I just love it there), and picking that for vacation doesn't feel like a sacrifice at all. It lets me do a little get-a-way to Disney too if I want to.
Disney is never on the list for us as a week long get-a-way. DH doesn't like it there, so that's a big reason. I like our annual main trip to be something we'll all really like. I do though tend to make it down for a little mini trip annually or every other year with DS. (I keep whatever I spend on this little get away close to 2 K). Freebie air helps make that possible.
This limited budget does pretty much leave out most international travel except Mexico, Canada, Caribbean, Costa Rica -- closer places, and it makes Alaska / Hawaii pretty much off limits.
We did let DS pick a special destination subject to our approval for a High School graduation trip and that was a week long trip to Hawaii (cost was about $7500) last year. We did a one time up of the vacation budget, though, with bonus money (upped vacation budget by about $2500 for that). // Glad we did it, but it take so long to get there and air and groceries are outrageous in cost. // I don't envision going back any time soon, as there are destinations that are easier to get to that I like more for way less money -- Puerto Vallarta probably being my favorite for a tropical get-a-way
I should also mention that these days we are not lonely planet travelers. We like reasonably comfortable places to stay and sometimes will pay a little extra if that works for that wow factor -- great space, great view, amazing balcony. Used to like to camp, but now getting older the pleasures while still there seem like more work than they are worth. And we have a higher vacation budget than we used to have. For us we don't really want to sacrifice creature comforts for more vacations days and are OK with just a week long vacation and a long weekend annually.
We travel to see relatives on the east cost annually and budget $2400 for that, but that is separate from my vacation budget.