Growing up in a quaint rural town where high-powered people from NYC liked to "get away", this is very common situation, and the inability to disconnect and adopt a slower attitude was, IMO, the primary cause of friction between the weekenders and the locals. They would physically get away from the city, but were unable to mentally release the blend of Type-A competitive neuroses that helped them get ahead in the city but just made them come off as obnoxious in this slower, quieter place.

I've found myself in this mode before, too. A couple of years ago I was preparing for weeklong wilderness backpacking trip with some friends. I'd recently quit my high-stress job to take some time off, and I had a few new pieces of gear I wanted to test before relying on them on a longer trip. When I looked at the calendar, though, every weekend before we were to leave was already spoken for.

I was worrying about it to my wife, trying to decide whether I'd just have to use the old worn out gear or risk it with the new stuff, when she stopped me: "why don't you just... go on Monday?" It took me a second to even get what she was saying—I was still so much in work-all-the-time-mode that my brain didn't even consider whatsoever the possibility that I could just... go off and go camping on a weekday. I was really baffled for a moment, and I've reflected on that a bit since, it's funny how you can be trapped in your own default operating mode and not even realize it.

It’s like those animals that walk in little circles the size of their last pen.

Except the pen is 1/3 of our adult lives.

Which 1/3 is that? It's black iron prisons all the way down

I've settled in a city 60% smaller than the one I grew up in. It's still a full-blown city, but there's way fewer of those competitive types - they all moved to where I came from.

I'm not really a resort person. But I do subscribe to some travel feeds mostly in the vein of maybe finding some places/attractions/restaurants/etc. that I'm not familiar with. The number of hyper-scheduled spreadsheets I see is amazing. Doesn't mean I don't often have some itinerary and even book some particular, popular attractions/venues. But the 30-minute block scheduling is something I do for work (if that).

ADDED: I'll just add that I created a loose spreadsheet for a ~week-long NYC trip with (I think) just one timed admission for a recently reopened museum and no times otherwise. I think I ended up dynamically scrawling over the printout with changes for most of the trip.

I have an upcoming trip planned in asia - never been before.

My firm rule is - have a loose plan, aim for one activity per day, an emergency option, or two, if the weather plays up, and that's it.

It's the type of plan that has worked for every holiday that I have taken that involves a different city to the one I live in.

This is typically what I aim for.

One or two core activities for the day.

If it works out for more that's great but it's not expected or necessary.

I've traveled with some people who seem focused on just getting pictures in front of as many things as possible which seems a poor way to really take in a place.

My family went to Hawaii a couple of years ago and in the exact middle of the trip we took a day doing absolutely nothing and it was kind of great.

I think that's a good plan. I do tend to book hotels, planes, and usually longer trains. But, especially for a longer city trip, I loosely map out--even if just mentally--things I want to see and do but, for example, one museum a day is mostly enough unless another convenient one is small.

one of the funniest things about going to NYC with a toddler was how very chill it was to go with a toddler

there are parks everywhere!

There are! Central Park of course. But also pocket parks all over the place.

I was like this but maybe not as stressful as you described. Still, I wanted to do stuff and see stuff during vacation.

After having kids, my habit changed. Now we enjoy going to local parks and walking around with no goals during vacation. This wonderful attraction? Nah we don't need to see it. If we can walk there, then maybe.

When we were planning a trip to Hawaii the first thing I researched was where all the local parks with playgrounds were. That way if we were driving and my son was getting bored or we needed to stretch our legs we knew where something was. There's usually a town, village, or city park nearby no matter where I've been. Even driving to Crater Lake through rural Oregon there were some great parks in the towns we drove through. Same with the drive out to Yosemite. This was the case up until we got within an hour or two of the park itself.

Some of the most enjoyable parts of those trips were hanging out with my family in a local park.

I have a hard time doing anything when in a nice resort. If it’s too nice, you just want to hangout at your pool villa all day and enjoy the view.

And if you're presumably paying a premium for a nice resort, why wouldn't you spend a lot of your time taking advantage of it?

Yes, if you want to get out and do things, better to go for low or mid range. You don’t want your room to feel like a huge sunk cost.

I tend to default to a midrange place as I'm not much interested in spending a lot of time by the pool. And when traveling on business, if meals weren't being covered, I didn't actually much care for resorts when I felt like a bit of of a prisoner in terms of meals etc.