Am I crazy???? The things we do for our children....

I've tried!!! I had no intention on even booking the Lake View room when I did..I was planning on going thru a travel agent but called when I noticed the dates were no longer available.
I ended up rebooking thru her and then cancelling my original res. We both tried, and both failed. :(

True, but I didn't want the craziness of the parks that day, that was the reason for the semi "down time" day before we head home.
1900 park fare breakfast is about the only character meal that I wanted which we haven't done/doing this trip.. And it does not fit in to our plans any other day. I thought if available he can do a pirate cruise after, and then we could head to mini golf from there. After that come back, relax, change, do a late lunch at Whispering Canyon and see the Christmas decorations.. I've always been curious about WL that time of year.
All of that being said- I definitely don't want to bore him that day!

Does anyone know when the pirate cruise dates become available for reserving? Every one was sold out when I tried to book one last trip.

But to me (and of course, it's only my opinion) that doesn't sound like a 'rest day' or down time to me, it sounds like you are running around a lot of places that aren't necessarily even close to one another. Like someone else suggested, I'd use the Christmas party day as your 'rest day' and spend the morning just relaxing at the resort before going to the party at 4.
 
I don't think you're crazy, but I do think you're putting an awful lot of pressure on this vacation to generate picture-perfect, pre-planned experiences. Furious? Really? What if you do get the reservation, but it rains every morning you're at CR and you don't have a good view of the castle anyway? Or what if your son isn't as excited about the view as you expect? Will that ruin the vacation for you? Because that sounds like an incredibly stressful attitude to take toward vacation planning.

As for your actual question, I have become a big fan of rest/resort days since running myself and my mother ragged on our trip last fall. I still wouldn't want to do a resort day on my last day, though. For me, the point of taking a break like that is so that you'll be fresh going into the next park day. If you think you'll be worn out by your trip (which it sounds like you will be), why not have a rest day earlier in the WDW leg of the trip, and spend the last day going out with a bang at you and your son's favorite park? If the cruise does wear you out with all its excursions, a rest day before three park days might be just the ticket.

I do think there's plenty to do around the resorts, as others have suggested. It might also be enough of a rest to (as someone else suggested above) use your Christmas party tickets on a day you don't plan to otherwise visit the parks. Sleep in that morning, have a late breakfast at 1900 Park Fare, relax around the resorts, and show up to the party that evening feeling fresh as daisies.
Oh, I won't dispute your "pressure" statement. Unfortunately, regardless of if it's a birthday party invite, birthday party, holiday, weekend trip, vacation etc.. I'm know to go a little over the top and cause self inflicted stress..But I am in a Bento Box Recovery Group. ;)..so I'm chilling out on some things.
The reasons for the view being so important are a few -
1. Because he literally jumped out of bed and ran to the balcony every day of our poly tpv trip. And I want to provide him with that again.
2. I am shipping our Elf on the Shelf to the port so he'll be waiting for us. On the last morning our elf "Luke" will have a present for my son from the North Pole.. Inside will be our Magic Bands. So, this trip is surprise as part of his Christmas presents.
3. I do feel guilt for not taking him to DW before the age of 5.. I went every year growing up, but as a single mother I just thought it would be too difficult with a toddler and me...so we stuck to beach vacays and I waited until age 5 to tackle Disney . Related to that, he doesn't have siblings so Disney World is a very limited time destination for us. I don't see it past this year..maybe a day or 2 in combo with a Florida trip..but we are doing a Mediterranean cruise in 2017, so definitely won't be back next year. So all of that being said I'm trying to condense as much as possible in our trips.

Our Christmas party day is not combined with a park ticket, so we will have that morning.

I think I agree with your last night out with a bang comment though.. We will be there Saturday - Wednesday. Party nights are Sunday (my original plan) and Tuesday. Maybe instead we will switch the 2 and make Sunday the non park day, which could be nice to sleep in since Saturday we'll be getting off the ship and then all day at MK.. We will come back to take a mid day break though...but I'm sure will be at the park late.

As far as rain- it rained pretty much every day of our 16 night Florida vacay in '15. We purchased parkas and made the best of it. In Key West it was tragically hilarious that we - Purchased water shoes. Paid park admission. Rented chairs. Rented snorkel equipment. Rented rafts. And purchased sand toys. After we got our spot set up and went in the water- seriously within 10 minutes a water spout showed up and a thunderstorm followed.lol. After the lightening passed we threw on our Disney parkas and walked around Duval St.. We definitely had more museum days than beach days that trip!
 
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But to me (and of course, it's only my opinion) that doesn't sound like a 'rest day' or down time to me, it sounds like you are running around a lot of places that aren't necessarily even close to one another. Like someone else suggested, I'd use the Christmas party day as your 'rest day' and spend the morning just relaxing at the resort before going to the party at 4.
I don't totally disagree with you. Maybe I'm just sentimental from last trip. Hands down my favorite day was our resort day..and it's funny bc that is the day he talks about the most when asking to go back to Disney. The memory that I cherish the most from that trip is watching the EWP and fireworks in our pjs on the balcony. During the fireworks he just randomly hugged me and said "I love you Mommy, this is the BEST day EVER." Maybe combined with the nostalgia of my childhood is what makes that memory so dear. But in all of my years as a child and adult at Disney World- that memory tops them all.
That being said- he proclaimed the same "best day ever" comment 2 months earlier on a 3 day camping trip.. So maybe I could have saved a few dollars and just gone camping again ;)
 
I love "rest days." With a boy that age at CR I would work in pool time (yes, it might be cold, but chances are he will be able to swim at least part of the day), look into the Pirates and Pals fireworks cruise. I am not sure about the Park Fare breakfast. Are those characters he likes? If so, go for it, but I would personally consider a redo of Ohana breakfast if he enjoyed it. Kids love repeats! I think a boat ride over to Whispering Canyon would be fun. You could even rent bikes there, or continue to the fort and fish. Allowing him some say in what you do next on a rest day could lead to some great memories! I always keep minigolf in mind, but we have never squeezed it in. It seems like a mini version of a park to me, and on rest days, we want to stick closer to the resort.
 

I love "rest days." With a boy that age at CR I would work in pool time (yes, it might be cold, but chances are he will be able to swim at least part of the day), look into the Pirates and Pals fireworks cruise. I am not sure about the Park Fare breakfast. Are those characters he likes? If so, go for it, but I would personally consider a redo of Ohana breakfast if he enjoyed it. Kids love repeats! I think a boat ride over to Whispering Canyon would be fun. You could even rent bikes there, or continue to the fort and fish. Allowing him some say in what you do next on a rest day could lead to some great memories! I always keep minigolf in mind, but we have never squeezed it in. It seems like a mini version of a park to me, and on rest days, we want to stick closer to the resort.
We can rent bikes and fish even if we aren't staying there? He would love that! We are doing Ohana on the morning of the party day. Stitch is his favorite character (outside of Star Wars) so that's a mandatory repeat :)
The other one he talk about is BOG..so we'll be doing that on our full MK day. He always asks to eat in the castle (especially since our 7 year old neighbor (girl) just came back and raved about it). But I'm still on the fence about that one.
I do think he'd like 1900 park fare - for breakfast only..and I've heard great things about it. Would be perfect if I could combine that morning with the pirate cruise that leaves from GF.
We'd still have time to go back and resort or (him) swim at CR even if we do whispering canyon later on, right? I've never been to WL and don't know how long the boat takes to get there.
 
I spent 11 days swimming in December this year ( 12/20-12/30.) it reached 85-90 every single day! Crazy, and likely unusual, but never say never! To reach WL from Poly has taken me 1.5 hours taking the two boats. I would plan similar GF-WL (though I realize you would be splitting up the travel.) yes, you can rent even if you don't stay there. The fishing is at the fort, bikes can be rented both at the fort and WL (though location has changed with current construction), I beleive.
 
I spent 11 days swimming in December this year ( 12/20-12/30.) it reached 85-90 every single day! Crazy, and likely unusual, but never say never! To reach WL from Poly has taken me 1.5 hours taking the two boats. I would plan similar GF-WL (though I realize you would be splitting up the travel.) yes, you can rent even if you don't stay there. The fishing is at the fort, bikes can be rented both at the fort and WL (though location has changed with current construction), I beleive.
This past year was abnormally high temps. I have friends in Orlando and my standard rule was that I never go north of Jupiter past end of October (Halloween Horror Nights), to visit, bc of their freezing weather.
Well, now I live in Cincinnati Oh, not Boca Raton.. So my idea of "freezing weather" has changed a bit.lol
 
I'm exhausted just reading your plans! None of that would work for my 6 year old. She'd be having meltdowns daily after 2 days of non stop.
I thought he would be able to handle the September trip bc we are always so busy anyway. We have zoo/cedar fair's kings island/water park/museum passes..and are at one per week..or somewhere else.. Granted Kings Island is not the size of MK, but it's not a small park and this will be our 4th year with season passes. He also plays sports year round since age 3 (only soccer and swimming then) but once he turned 4 baseball started, and then at age 5-golf camps and 4 days per week football. Right now his baseball and swimming are overlapping until end of April. So he's constantly on the go.
What I learned from september's trip- None of that mattered. 16 nights is MUCH too long of a vacation for us at this age. And 8 nights at Disney world is something I never see us doing again.lol. I know people do that or longer per year- and kudos to them..But was a one and done for us.
 

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