I've never taken my DS out of school before for a trip, but this is the first real trip we are taking since he's been in school. I have no problems taken him out of school for a family trip for a few reasons. First, the only time he gets more then two days off in a row is summer and Christmas. Because of a visitation schedule with my son's father these times do not work for us. Also, it's a long trip from North Dakota to Florida. So, if we are going it's going to be a multi day trip, not an extended weekend away. So, whether it is for free dining or not, we would have taken him out of school for a vacation. His school is used to it, especially in the winter when a lot of families escape the cold ND winter.