Vacations with my wife before we had kids. We were trying to be frugal and did almost all of our vacations with family. They were universally horrible because our families would leave their frickin neighborhood. But when we went off and did something interesting, we would get guilt trips from the family that we weren't spending time with them. We really didn't save that much money as we had to fly and rent cars. Now with kids, we are again stuck with having to dedicate at least one vacation a year to visiting relatives (the f-ers NEVER come visit us . . . we always have to go to them). I finally said f-them the past two winters and took the family skiing. It was so much fun that my kids were crying when we had to leave. Also, I missed out on going to not family friendly places with my wife and won't get back there until we are much older and boring.