Re enjoying your trip vs worrying about drivetrain and time spent cleaning--when on a trip or not, my rag wipe of chain, pulleys, quick rag floss of the cassette if needed (wheel on bike) and then lube and wipe down again after spinning cranks a bit---really must not take more than 10 mins.
So doing this every x days depending on conditions really isn't a big deal, and anyway, I like the quiet and smoothness of a clean drivetrains, and knowing the parts will last longer is a bonus.
I dunno, I'd equate it to brushing and flossing your teeth, its just part of the routine and certainly not a hardship or takes much time.
Maybe because I'm the house bike mechanic and take care of 5 bikes plus neighbours bikes sometimes, I've got my rag system down pretty fast.

For the once in a while cassette rag floss, after I do a quick smallest cog floss, I put the chain in that small cog and can vertically floss the rest of the cassette in 2 mins maybe. Using a thinner lube helps here as its way easier to floss clean than thicker stuff, and especially if the gunge hasn't been on there forever.

Basically I find more frequent clean and lubing is just faster to do, with bonus of cleaner and well lubed always.

I always have a small bottle of chain lube with me on a trip, keep old ones so I dont have to carry a full one, plus I do the "one drop per link roller" thing so I dont use much.