My father has always struggled financially. Recently, he was very ill and has mostly recovered. He wants to take my mother on vacation after all they went through but he can only afford a minimum basic vacation. Would it be ok to pay for them to go on a nicer vacation with maaser money, because they need it very badly?
The rule regarding giving tzedakah is that we have to give them according to the person’s needs. Therefore we have to give them whatever they need, but not what would be considered an unneeded extra according to the individual situation. Therefore if according to your understanding of the situation it is something that will be beneficial to them, then it would be included in tzedakah and you can use your maaser money for it. However if it is just an unneeded extra, then it should not be used. From what you are describing, it sounds like they do need a better vacation then what they are planning, therefore it would be permitted to use your maaser money for it.
As a side point it is important for you to know that if a person’s parents are in need for financial help, they are from the highest priority to be given a person’s maaser money, besides for fulfilling the mitzvah of kibbud av v’em. However on the other hand, when giving money to a parent, the child should be very careful to do it with tact, and do it in a way that they will not get embarrassed by it. This is because parents can easily get very embarrassed to take money from their children.
Y:D 249-1, 250-1, 251-3.