When I was younger, I definitely would have chosen new places. So much to see!
That still sounds appealing, but as you get older, the number of places you've visited and loved grows. I find myself thinking, "It would be wonderful to see Prague." But right on the heels of that comes, "Well as long as I'm over there, it would be a shame not to visit Venice again. And Florence. And Rome. And Paris." Pretty soon, there's no money or vacation time left!
For longer-distance vacations with my husband, I definitely prefer the new (though we also used to revisit favorite B&Bs a lot, back in the day). For family vacations, it's been hard to branch out. We've gone to Oregon every summer, where my parents and two sisters (one with kids close to my kids' age) live. I plan to do something different this year, if I can work around my daughter's internship/potential-foreign-study schedule, because the kids are older now and finally bored with the repetition. Plus, since we have to stay in hotels now instead of with my sister, it's expensive enough that we might as well go on a 'real' vacation. I don't regret how we've spent prior years, but we need a change (especially before the kids run off to college).
It's funny, with family trips our biggest impediment is my daughter. She doesn't want to look at nature (Grand Canyon, Yellowstone, Glacier), or visit museums or old buildings (pretty much all of Europe). It wouldn't be such a problem, except that everyone else in the family likes those things, and has no interest in shopping or just people-watching (which are what she enjoys). My daughter's vacation limitations are like her food limitation, including the part where she complains that there isn't enough variety (and then hates what variety there is).
This is why I need to win the lottery, so we can Do All The Things (and hire babysitters)! But no movement on that front yet...
Thanks to matchboximpala for the topic!