What's your definition for this case of not difficult to get to? You talking more along the lines of time to get there, or less connections?

Going JFK-LAX-HNL (or OGG) is extremely easy especially if you do J or F on NY-LAX transcon on AA. BUT, that's a good 11-12 hours of flt time there and 10-11 back.

For super easy, just fly down to the Caribbean nonstop from JFK. I personally would choose St Maarten.