We’ve taken the kids to Destin Florida for the past 3-4 years. Seen about everything there is to see. I’m ready to move on to a cruise. I get a tad bored going to the same place. My wife on the other hand can do the same thing repeatedly and not get bored. I guess it depends on what you’re looking for and what satisfies your curiosity.
Great question, Sarah. I probably lean toward new places, especially if outside of the United States. I do have a list of places to revisit, though, which will happen in retirement perhaps (although I’ll unlikely get to return to all of them). Places abroad I’ve been to more than once include London and Paris, but there is so mich to see there that it hardly feels like a return visit. Same for New York City stateside.
Which leads to return sites. NYC, as I’ve mentioned. I’ve probably been to Chicago more than anywhere else, and there are places in that city I like to visit nearly every trip. At the turn of the century, I used to travel to San Francisco A LOT for work, and would tack on a few days of vacation. I don’t know what it was, but I would frequently get stopped on the street by tourists asking for directions somewhere–and I always knew what to tell them.
I’d like my next trip to be Slovenia and Croatia. In 2017, though, we’d like to return to Copenhagen for our 25th anniversary (we were married there).
Sarah,
I don’t travel as much as you do but this is a dilemma in my household every year.
I am the “want to go back and explore” person. My wife is the “I want to explore some place new” person.
We have to strike a balance between the two of us.
Benefit for me is that I get to explore some new places often. For her, it is just the opposite. She finds that several of the places we have been are worthy of 8 or 10 trips back to reexplore. (If we only had the time and money. The proverbial problem.) It is not an easy balance to obtain. Some places like Japan, France/Italy wine areas and Africa will draw you back every year if you aren’t careful. 
I’d like to think I’m relatively adventurous, but I’ve been to Hawaii almost 30 times so who am I kidding.
Part of my problem is that I can’t go somewhere new without having to cram in everything I can. In the end, those trips are experiences, but are much less relaxing. With work really stressful for both my wife and I, we relish being able to chill and recharge. Hawaii is the perfect spot for that. It’s definitely a bit exotic, but knowing the ins-and-outs makes it carefree and it’s easier to get to than the east coast for us.
We also find it extremely hard to get more than one work week off. That makes it a lot harder to go on the more adventurous trips. African safari, Tahiti, Philippines, and Australia, all being more than a week, will take us another 7-8 years to get to.
Its a great question. I think its a function of where you are in your life/family/career arc. The more demanding any/all of these are, the harder it is to make the effort to go somewhere unfamiliar (all that research!).
We’re just lazy, truth be told. Our jobs are pretty full-on at the moment so we default to what we know and love, what will allow us to switch off, and where we can go without having to engage our brains, at least when it comes to travel and logistics.
I hope that changes over time though. I have two pals who are about to head off to Ethiopia for Christmas. They’ve been to Antarctica, the Galapagos, Sri Lanka and all manner of points in between and I marvel at their enthusiasm for new places (and ability to take extended periods of time off!).
So for us right now its Return. But I hope it becomes Explore.
As someone who once suggested going on vacation in NYC (go to museums, gardens, eat out, etc.) in preference to getting on a plane I don’t think I’m qualified to answer this question
You should have seen the look that Arnold gave me…