Have you ever heard of double Landlocked, of course you have, Boston has that but with being an island, it's an island in a larger island.

So have you ever heard of the Erie Canal and the Illinois and Michigan Canal?

Amtrak are you also drunk?

Nope

It's the largest city in New England so I choose them. Would you rather I chose Yonkers?

I actually didn't know it was the biggest city in New England (not much competition I suppose). But then what's the second island? The American continent?

Everything east of the Mississippi is an island because of the Illinois and Michigan Canal

and then because of the panama canal it's a triple island.