I have a Disney planning conundrum so, of course, I turn to my Disboard friends for help. Here goes... Currently, DS #1 is a junior in high school, and DS #2 is an 8th grader. Both are in their schools' marching bands, and they plan to be in marching band together next year when DS #1 is a senior and DS#2 will be a freshman at the same high school. Next year will be the ONLY year both boys are in high school and band together. The band plans a trip every three years to perform at WDW, and yep, you guessed it, next year is that year. We are WDW vets, and of course, want to go to WDW to see our boys perform at WDW and to enjoy all things Disney for a vacation. Both sets of grandparents want to join us for this once in a lifetime situation too. My parents have been to Disney a few times; the most recent trip was with us in 2014 and we stayed in a two bedroom villa at OKW, which worked incredibly well. DH's parents are not amusement park people, have never shown any interest in Disney, think we're nuts for going many times, BUT they really want to go to be able to see both grandsons play. We want everyone to have an amazing time! Here's where things become difficult...our school district hasn't finalized our calendar for next year yet. So, the band will go either over spring break or in June when school gets out. The band director doesn't know which time frame yet, and since the calendar hasn't been set, we don't know when spring break or the last day of school will be, although we can make an educated "guess". We want to stay on property, we'll want the regular dining plan, and we'll want park hopper tickets. Since the two bedroom villa set up worked well when my folks travelled with us before, ideally we'd like to get a three bedroom villa so we can all be together (me, DH, DS#1, DS#2, my folks, and hubby's folks). We definitely all need our own space, so a three bedroom villa is a requirement; we could not make a two bedroom villa work. If a three bedroom villa doesn't work out, we would need to book three separate rooms at the same resort; we are a close, loving family...but there is no way we could bunk in the same hotel rooms. Each set of grandparents would need their own space, and DH/DSs/I would need our own space too. We are not DVC (although we'd like to be someday...once we are done paying for two college educations!) and I know three bedroom villas are sort of like unicorns when it comes to making a cash booking. So, here are my questions: 1. Since packages aren't out yet, should I book three rooms somewhere for the week I *think* will be our spring break next year, with the idea that I can modify the ressie once we know when the band will go? Is it smart to book three rooms only, with the idea I can parlay this into a package/villa booking later? 2. Or, should I sit tight and book later when we have a definite date? If so, when should I book? I'm guessing spring break will be the last week of March in 2020. 3. I know that villas don't become available for cash bookings for a while. When, exactly, do they become available, and how impossible is it to snag a three bedroom villa? Are there any strategies for cash booking a three bedroom villa? 4. I would love to book a three bedroom at one of the monorail resorts, but I recognize that I may not have many choices regarding the resort. Which resort(s) would I be most likely to book a three bedroom villa in? I apologize if this should be posted in the DVC area. I just wasn't exactly sure which place made the most sense. Please feel free to move this to wherever it makes the most sense. Thanks so much, Dis friends! Any and all advice is so greatly appreciated!