For my first o/s trip I didn't really have a plan as my SIL basically organised everything

. For our 2nd it was a P&O cruise so I only had to organise flights and the cruise and shore tours and that was it. On our last trip I planned a lot more but in saying that, much of what we did was kind of made up on the go once we got to the U.S. We had things that were must-dos of course, like our cruise,
Disneyland, Montana, Vegas and that was really it. I printed out a blank calendar for the months we'd be gone and filled in all the firm bookings and worked from there. I like to see at a glance what we have to do and when and work from there. We just filled in our gaps based on what we came across on our travels.
I realised I planned our last holiday, and am tending to do the next one, similar to how I plan for lessons. I have a visual planner (the calendar) and I have filled in the dates for our booked cruise so far (like it's a set exam period or an assignment due date I guess) and then work from there based on what we need to do and be where when. I know our cruise will sail the day after school term ends for Christmas so we will aim to be in Florida for a week before then. I can't book flights until later so I can't fill that in. We plan to be back in Montana for Christmas and New Years so I've tentatively penciled that in. We have to be back home at least half a week before school returns for term 1 so there is my 'end' date. As I go, I will be able to see what days I have available to me on the calendar and work from there. I only threw out my last trip's calendar only a few days ago so I can't even post of picture of it to show my 'working out'.
My SIL is also our TA so she has the formal itinerary for us on her computer and I keep a copy on each of our two email addresses plus two paper copies - one in my luggage and and another in my little folder. I'm not as 'organised' as others with spreadsheets or apps or day to day plans.
This is what I took last time. I got the A5 zipper thing from Officeworks (bright pink so see easily in my bag). It has on one side a zippered pocket and some pen holders with a little open pocket at the top. Underneath that is a thing for slipping papers or whatever in. On the right side is another full length pocket with a separate pocket at the top.
I printed off tickets and things and put them in little plastic pockets that I labeled 'tickets', 'accomodation', 'esta' etc. That way everything was there and ready to go. It was all put in order of dates when I'd need them. For accomodation I would throw them out once we had stayed at the place, but I also had a hard copy on email anyway. I kept copies of loyalty cards in one of the right-hand side pockets, plus had a piece of paper with addresses and phone numbers of family members for post cards or whatever (we only sent a couple anyway). I also had a list of tips for DL and
DCL reminding me to get pillow cases and photo mats signed, get 1st visit badges etc. I was going to keep our passports in there but I ended up being one of those women with the passport thingys dangling off her neck instead. I carried my pink folder through the airport with me and then kept it in my carry on bag until we got to our destination.
Other than that, at the moment I've got bits of paper all over the place of things I've noted or printed off. I have an old Winnie the Pooh folder that I used at uni with dividers that I'm thinking of using to organise things in, but then again, I love stationery and keep buying cute spiral A4 notebooks from Typo that I think will be great for keeping notes in

I'm still in the early stages of planning and this is where my little pink folder is up to right now...
I love reading how everyone else plans. I'm nowhere near as fanatical as others I've read about on other threads

I'm sure if some could schedule in toilet stops they would