I believe that you really cannot put a price on memories of great family vacations. By starting when your kids are young, you will be able to create more of these memories and also establish a tradition of going on vacations as a family.
MasterCard's advertising campaign that promotes creating "priceless" memories is quite ingenious. While I do not advocate charging an event or vacation trip on a credit card if you won't be able to pay the bill off in its entirety, I completely believe in the idea that having great family vacation memories are truly something that you can't put a price on. While you can buy the airline flight ticket or vacation package, you certainly cannot buy the memory of a great vacation trip.
This becomes especially true for families, because taking family vacations gets more difficult and more complicated as children grow older. In our household, we were always very frugal about daily and monthly expenses however when it came to spending money on vacations, we always tried to make sure that we took a family vacation each year. Due to our naturally frugal nature, we would still try to get the best value when we were planning our vacations, but we hardly ever decided to not go on a vacation just because of the cost. Where we went was somewhat dependent on the ages of our children, but no matter what, ever since the time our kids were ages two and four, we tried to always make sure that we went on a vacation each year.
In determining how early to start taking our kids on vacation, our logic was to start slow and just see how things went, going on shorter driving vacations when the kids were younger. We didn't try take our kids on an airline flight until they were ages four and six. In general, we tried to go to different destinations each year. We only went on trips in the United States until they were teenagers, when we took them on their first international trip. Our thinking was that given the extra cost of an international trip, we wanted to wait until they were mature enough to really appreciate the trip, which they did.
I firmly believe that you will never regret the money you spend on a great family vacation. You don't hear any stories about someone on their death bed wishing they had saved the money instead of spending it on a vacation. Those types of regrets are usually the other way around. That being said, any trip or outing is only as good as you make it, so keeping a positive attitude and having patience with family members can also help increase the likelihood of creating priceless memories of family vacations.