I usually travel alone, so I don't worry about it much. I don't have business trips to really deal with, so I can wear when and how I please
I really don't travel all that much, but on my excursions to Norcal I generally wear the whole weekend, unless a situation comes up that I can't.
It comes and goes for me though and, like you, i guess I get 'bored' and switch back to conventional wear.
On my trips to Monterey for the car show and historic races, I wear all day for the races, since the track (Laguna Seca) is HUGE and the portable bathrooms and disgusting (as usual) so I'm in a diaper all day for that event.
The car show is hit and miss. They again have the portable bathrooms, but I'm usually with a friend and his family so I have to be a bit more careful. though the last couple of years I have worn to that event also with out circumstance
The last road trip I was on, I traveled with a couple of other friends up to San Jose (yes we found the way) and was wearing Abena M-4's both up and back, with out issue. So that seems to work out really...so far anyways.
Other places *shrug* it depends on who, what, where, when and why. The last cruise to Alaska I was on I had a pull on diaper and some plastic pants packed and only wore them a couple of times. I developed the runs on board (probably due to the water) so actually disposables would have come in really handy, as I didn't want to be washing the same diaper everyday. Laundry on the ship was EXPENSIVE too.. $3 just to use a dryer! so I bit the bullet and only wore when I wanted to, which was a couple of times.
I don't like packing diaper if I'm flying, just because of all the ^%$#@@! security these days and potential hassle, so I avoid it. If I'm going anywhere, I usually drive.
So for me it's kind of basic, wear for road trips and what ever events, and any other time I want or can. I like driving in them since it saves on stops and I can get to where I am going and not hassle with longer trips than necessary. At the destination, if I have been there before I wear also, and don't worry about it, since I generally wear extended wear diapers anyways, I can go a long time with out worry about leaks etc. My baggy shorts usually hide most everything, so all is good.
I haven't ben on an 'extended' trip much, so i don't know how I would work things. It might just depend on where I'm going and how long it will take.
Much of this also depends on my mood at the time. I try to work up to the trip with minimal wearing, so I have something to 'look forward to' in a sense, so i'm not 'burned out' before I even start.
Thats it for me really, as long as I have a hote room to myself I'm good to play how long it lasts though is another matter. I'm usually good for a weekend or day or 2 beyond, but after that I'm done and can wait a time before indulging again.....just the way things work for me.