Oh yes, definitely.
Another option is to have dinner someplace else in the area and just have an ADR for ice cream. I really like the No Way Jose Sundae, so my plan is to go there for lunch the day of MNSSHP.
So you’re wanting to take an Uber to the Boardwalk, walk around to BC for dinner at Beaches & Cream, then boat to HS? That sounds like a fun way to check out the Boardwalk for the first time. (You could also boat across to the YC/BC but that could entail some backtracking, on both sides of the lake).
The boat ride might take 15-20 minutes if you get right on it. The stops when we were there last May were: IG-BW-YC-Swolphin-HS and back again. One-way is about 30 minutes total, IG to HS.
Those serendipitous discoveries are sometimes the best, aren’t they? Especially as a Liner, it’s fun to get lost every now and again. As much as I love to plan, the most magical moments usually happen by chance.
Consider the timing of the street performers when you go. We’ve stayed at the boardwalk multiple times and have only caught glimpses of a performer here and there. I think the ideal time is between 7-9pm