I have a 6:30pm ADR at The Wave, but I’d rather 'Ohana. I was able to get 6:50, bug that is cutting it too close with the long wait times I hear about. Of we check in at 6:35 (party of 6 or maybe only 4) would we get in quickly enough to be back at the contemporary dock by 8:30 for the pirates and pals cruise?
I think you’d be cutting it close. If there’s any delay with getting seated at 'Ohana or on the monorail to the Contemporary, you’re going to risk missing your boat. You should factor in waiting for the monorail, a potential delay, the walk to the dock from the monorail station at the Contemporary, etc. Personally, I wouldn’t want to risk it.
And isn’t there a good amount of time before the 8:30 P&P cruise devoted to the snacks/desserts/character greets? I think it’s definitely cutting it too close.
And if you’re a glutton like us, you probably won’t want to do much after eating at Ohana 
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There’s always a chance you’ll be seated early if you arrive early for your 'Ohana reservation. I’ve been seated well before my reservation time at that restaurant in the past. However, that’s not a guarantee.
I’ll also add that the one time I did the Pirates Cruise I was disappointed that I didn’t want to eat more Mickey bars before we went to sea, because I just came from Be Our Guest for dinner and couldn’t turn down the cupcakes there. It doesn’t ruin the experience not to eat cake and other sweets before the cruise, but if you’re the sort that feels like you have to “get your money’s worth” out of an activity by eating as much as possible, then coming from 'Ohana could affect your ability to do so.
Or you might end up like us. As we walked up to the monorail at the Poly, a monorail pulled up. Yay for us. When it was still sitting there an hour later and we were in ginormous lines at the boats, trying to get out of the MK AREA.
We later found out it didn’t move again until sometime late that night.