Hi Griffen,
Most Caribbean cruises out of NY have a 1-Way return flight from Puerto Rico which is about 10-11 hrs. to LA.
I've also heard nightmares stories (from the board) trying to fly out of San Juan.
The thought of a 10 hr flight after a relaxing cruise is a "turn off".
So far I haven't found a cruise going the opposite route (1st fly to the Caribbean - cruise to NY and fly home from NY), 4-5 hrs is doable. We should continue to be in a relaxed "just-had-a-fabulous-cruise" mold when we get home.
Do you know of a roundtrip cruise to the Caribbean from NY? Which line?