Yes, some love being able to switch off and have someone else handle all the logistics. For me that's hell, and being stuck on a prison ship (erm, I mean cruise ship) would make it even worse.
2-4 weeks in one place gives you a great chance to really get to know a place, but it requires a mindset of revelling in the mundane being good e.g. every day / every other day visiting the market for fresh produce; exploring local food shops; finding a bar/cafe that becomes 'regular'; exploring not just the centre, but also finding out what's appealing in the suburbs; Attending local events, from little festivals and even local clubs. In short the embedding in the culture that's the polar opposite of those cruises and 'see it all in a week' tours.
For day trips, having a list of 'options' prepped helped us a lot. Knowing how we'd get there, if there's a good day e.g. market day, or avoiding a half day closing day, a few restaurant options, a few key shops, any local attractions worth a look. That's then all available to us to either influence plans the evening before, or even to do something 'on the spur of the moment'. It was enough to avoid us feeling lost and confused, but was never in any way a 'schedule'.
We'd also treat some day trips as a 'sampler', not attempting to 'see everything', but instead simply enjoying what we did, and aiming to get a feel for whether we'd like to return another time, perhaps even for an extended stay.
If the place you choose has a good train network (e.g. Italy, Germany, France, Holland etc.) then longer day trips can be enjoyable. A direct train of 1-2 hours can be comfortable and fast, with the potential for a picnic breakfast or supper on the train to bookend the day. They can be a good antidote to feeling the days get a bit samey.