is it ok to just wing it on a cruise?

To me winging it would be having zero plans :D
I also think you have enough plans here with some room to just do what you feel like. I wouldn't schedule every moment of a 4 night cruise anyway. It's way too short to be running around. Just enjoy being in the moment.
Hope you and your son (and parents) will have a great cruise!
 
I like that, "moderate level of planning" makes me feel better even though to me having one anchor thing per full day is not really much planning at all.

Considering that, on our last cruise with friends, planning on some days consisted of: get out of bed and meet for breakfast at 9:30 am, make sure to get ice cream on deck, maybe we'll watch a movie in the afternoon or sit on deck together watching the water, I call what you're doing moderate planning. :)

I didn't even realize they did the stingray thing at CC until just how either but I think he will like that too

We did that a few years ago and enjoyed it. DH fed the stingrays - I'm allergic to seafood so I couldn't handle the shrimp they were using but he thought it was pretty cool.

I think snorkeling at CC is more hit or miss, though he is going to love the Disney surprises as much as the fish.

That kind of stuff is harder to plan day of. I don't even know how fast some of it books honestly but I hate leaving that stuff to chance.

I'm not big on snorkeling but we've done it a few times, including at CC. It depends on how much you've done before (and what your standards of what constitutes good snorkeling) and what you want to see. In Grand Cayman, we saw a lot of fish but it was pretty neat doing it at CC and seeing the things they've hidden there. Kind of made it a bit more interesting and an adventure but it depends on what you like. We got some really good shots with a waterproof camera there. We had planned to do the snorkeling at CC where they take you out farther on a boat but the waves were too high that time so it was cancelled. I don't think it's terribly difficult to rent the equipment day of if you're just going to go to the snorkel area at CC; I don't think they ever sell out.

i would have been happy to not get off in Nassau and just enjoy the ship but the kid is so over the moon excited to be in a foreign country that's not Canada that we'll be getting off the ship there, lol. that was originally my plan but he was not into that.

If he's never been before, then I can imagine he wants to see it. We did a tour our first time to see the fort and the island; I do think you have to get off at least the first time.

I really do think you've got a good mix between planned and go-with-the-flow and shouldn't stress about whether you've got enough to do. We've done 10 cruises on DCL and still find plenty to do but also just enjoy zoning out or impulsively joining in on something or stopping to watch whatever's going on or getting pictures with characters. Don't forget to just enjoy the time together too!
 
The navigator's are full of activities, especially on the sea days. And some kids are happy just spending the whole time in the pools, but the pools may be quite busy and full on the Dream, so that may not be a viable option most times. If he really likes one of the kid's club counselors or makes a friend while in there, he may never want to leave the kid's club. It's hard to plan for that kind of thing in advance, with any children. I agree that he most likely will love the Midship Detective Agency game that you can do together, or with the grandparents, at your own pace.
 
Be sure to check out the Mid Ship Detective Agency.
It’s an interactive game for both kids and adults. It takes you all over the ship. Lots of fun.
 

I decided to try winging it on our 3 day Dream cruise. I hung out a lot here so I knew a fair bit but decided not to do my usual extensive researching.

It went ok but my family wasn't crazy about it and neither were the friends we travelled with. They are used to my knowing the answer to whatever question pops in their head and were taken aback at the number of times I said, "I don't know" (I surprised myself too!). My friends wing it when they are by themselves, but they love it when I do the work for them and we have agreed I shouldn't try winging it again haha.

It was a bit annoying getting lost a few times because I hadn't studied the deck plans closely. It was also annoying having to stop to figure various things out or find a CM to ask because I didn't know the answer. It was VERY annoying going out for our adult night (close to midnight since it took a while to get the kids settled for bed) only to find every single food venue on the Dream shuts down at midnight. We finally had to go back to our room to order room service and hang out (we didn't want to worry about waking up the kids). Good thing we had a balcony!

I'm a planner by nature and I hate "wasting" precious vacation minutes figuring things out. We still had an amazing time. But I would have preferred planning. Much easier to change plans on the fly IMO. Also, we missed the Detective Agency....wahhhhhhh!
 

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