So I have a couple of short room-only trips booked so far this year, 4n in early April and 4n Mother’s Day weekend (gotta choose onw). But I’m kind of thinking that I may want one long, family trip instead. 4n sounds fun, but with DD3, flights that are either complicated or at annoying times, and my relentless FOMO, that 8 night stretch is sounding like the length I would need to work in that down time (and a UO day) that made our March 2020 trip to WDW so fabulous. Trouble is, DS8 has some LDs (is that what we’re calling them these days?) and barely keeps up with twice a week tutoring. I can take him out two days, mayyyyybe 3, but a whole week just creates way more work for his teachers because he won’t catch up quickly, and is a bummer for his self esteem. So, if we want to go on a long stretch, our options are:
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March 3-12. Right now, we are actually booked to go to Iceland, but that looks unlikely. We’ve gone this time of year before and loved it, but the crowds do build as the week rolls on. But this year, TP is calling it 9s and 10s all week (UT says 7s, others say less earlier in the week). The weather is fab, but we’ve done F&G, EE won’t be open (family fave), GotG not yet, and room pickins are slim at this point. Potentially too cold to water park (it was last year)
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June 11-19. Again, right now booked on a Mediterranean cruise because I’m insane and the rate was so good I couldn’t say no (balcony room for 4 for 3k). Prob also getting cancelled, mainly because DD3 may not be able to get off the ship unless it’s in a cruise ship bus and that sounds awful. This is the day after our son’s school year ends. We have heat and humidity in VA (and live in a swamp on the water), but FL is still it’s own kind of beast. I am not a fan that kind of heat, and neither is DH. The upside is no worries about school, and TP says MUCH lower crowds than spring break, plus more room availability, EE open, mayyyyybe GotG?, water park time!
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Thanksgiving week. The crowds this week are a whole lot of insane, but I could probably swing us going the Weds or Thurs before (1-2 days of school missed) to get some park time in before things go totally nuts, and we’d def do an AH event or two. Upside is CHRISTMAS YAY! And weather! Downside is that this would probably mean DH is on call/rounding on Xmas day, and the family would be grumpy that we didn’t host and judge us for choosing WDW over them (sigh).
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Just stick with the long weekend in April/May and add a quick 2n jaunt for a Xmas party in Nov/Dec. Pros are avoiding crowds mainly, and weather, and room choices; cons are these weekend trips are more “trips” than vacations because you don’t have time to wind down. I have a really, really hard time being at WDW and not being in the parks, but if I’m there for 7n, I get parked out on day 4 and then get to explore all the resorts, restaurants, pools, water parks… and I won’t do any of those things on two short trips. I’ve tried and I don’t have the self control.
WWYD?
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Lower crowds and the trip is long enough that you can do afternoon breaks to deal w/ the heat.
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Can you actually allow yourself to slow down and enjoy the 8 days? If so I think June is your best bet. It avoids the crowds and family drama. It will be yikes hot so you can’t crush the parks like you could in better weather, but it’s doable at a relaxed pace.
If you can’t chill and enjoy I’d stick with the shorter all out commando trips.
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I CAN chill. I’ve done it before and prefer to do it that way when family is with me so we don’t have mega grumps everywhere. Good question though. Cause I don’t have a whole lot of chill 
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Longer trip in June. Crowds are insane and unpredictable. A long trip gives you the opportunity to hide at your resort if need be. 
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Ok, but what about with a 3yo who refuses to nap? Making early am and late pm touring tough. Though I suppose with that much time we could just pick one each day.
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I would invest in a really good carrier designed for toddlers, and wear the 3yo (facing you to reduce distractions) once they need to crash.
While carrying a 3yo sounds daunting, it is totally doable with a good carrier.
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True. I can’t do the carrier (couldn’t even when she was a babe) bkz of sacral issues and DH won’t bkz spinal stenosis is one of the most common career enders in his field, but a comfy stroller and fan can solve lots of problems!
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When mine were that age (and would ordinarily be out of naps at home but need one at Disney) it was easier to let them nap in a stroller than try to get them to go back to the room and nap.
Another vote for June here. No school/additional home worries = true vacation mode. And 8 days is fabulous.
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June! 8 days is amazing. Our family did mostly rope drop til mid afternoon. One late night. It was great. 2yo napped in the stroller some days, others she just powered through. You’ll get to enjoy some good pool & resort time too.
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Seems to be unanimous, then. Do yall not know about the heat?!
ETA I originally wrote “seems to be anonymous” and omg I’m gonna need more sleep, children. MORE. SLEEP.
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Lol! The heat is hot. Fair point.
I took my kids solo in late July a few years ago and we had a ton of fun. It was super hot but the rain mid-day would sometimes help clear the air out a little bit.
Otherwise, I’d say as long as you manage your expectations with how easily you can “power through” with the heat in the afternoon you can still have an amazing time. I think that trip with my kiddos I arranged my TPs intentionally with indoor rides/shows during the heat of the day if we stayed in the parks through the afternoon.
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We’ve been to WDW four times as a family. Only in August. So heat…I understand what you’re saying here. But we have a lot of the limitations you have in terms of going during the school year - both of us are educators so we really can’t miss. It’s frustrating but in the end, the kids never cared that we were there when it was hot or crowded.
Now napping - our first trip DS was 4 and DD was 6. Napping was an absolute must. We stayed at the Poly and were back at the room by 1 or 2 each day, and then hit a park again at night. That worked better for us with two nappers. We have actually never stayed at a park all day even when they were older. This year, they will be 13 and 11. No idea what our game plan will look like lol. Just roll with it, try napping in a stroller. If it doesn’t work? Try going to inside shows. And then if that doesn’t work, head back to the room if you can.
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We always go in late July or early August, it wouldn’t feel right being there without the heat 
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