Yeah, if you’re asking the question that I think you know the answer to, yes, it’s possible to land in Boston at 11:30 and make the ship on time. Frankly, it highly likely you will. I only flew when required for work and remember making many 9:00 am Boston meetings from NYC. Sorry, it’s been a while so I can’t give time estimates. But do standard ETAs matter? I noticed you emphasized “if” plane lands on time, because you know it’s likely that and all those other unexpected variables that would be the reason you might not make it.
But, man oh man, would I be looking at Amtrak trains tonight, or driving. I would hate the thought of the things that could go wrong. But I’m a worrier. And I hate to fly now, so for me catching the ship at first port is off the table (but it looks like you’d be willing to do that if you had to).