Parents and their kids should visit different places because kids need to explore and it also helps parents because once they get older they probabaly wont want to do it because it will be harder for them and it helps the kids because they can make more memories just in a different setting
Education is the single biggest determinant in one's success, and it comes in many forms. Travel and exposure to different places, different cultures and even different foods encourages flexible thinking and discourages narrow, ethnocentric thought. People around the world do things differently, but we all share common needs, and travel puts this on display. Hopefully, when the opportunity presents itself, people choose to travel often and to diverse locales.
Each year I go on holiday to different places each year and I have only ever been to Barcelona and Rome twice each (I went at the same time because we were on a cruise). I suppose it is okay if you have booked it for say a 10 year block but otherwise, travel about the place. Not being boastful but I am very good at geography and partially because I corrected my teacher about a geography question about the Grand Canyon because he thought the Colorado River ran through Brazil. So yes it is better to go on holiday's to different places each year.
Of course it's interesting to visit a new place each time. But you can't say that you've experienced the culture of a place which you've visited only once. It's not possible to get to know the place in just one trip. You should visit the same place in different seasons, during different holidays, so that you could have not just a "touristy' kind of knowledge and experience of the place.