Math's Not My Strong Subject, But....

So here's the problem.

I want to go here with my girlfriends for a week and lounge about on Orange Beach:

plus I need to have time off for a week or so for family things (reunions, weddings... they all seem to be scheduled for July and are all across the continent)

And this is my boss.:

And this is my wallet:

So I'll be working on this square peg/ round hole problem, because obviously if it won't fit the first time, you're not using a big enough hammer.

Photos thanks to google, cartoon stock, and nohodamon