Originally Posted by Herb687

60. (1982) Back in 1982, twin engine jets were not widely used on long predominantly over-water flights. Indeed, from the east coast of the United States, only one airline operated 737 flights to destinations in the Caribbean over 1000 miles away. Identify that airline, the U.S. gateway airport from which its 737 flights departed and the two Caribbean destinations so served.
HINT: It's a foreign airline

Offhand, I can think of two Caribbean airlines who were big operators of 737s. The fact that there are two Caribbean destinations as opposed to just one involved is leading me to guess Bahamasair. Bahamasair 737 EWR-NAS and EWR-FPO?

Herb, those are excellent guesses - ones that I'm gonna have to get back to you on. So far as I know, Bahamasair did not commence service up to EWR until 1983 or later. My 1982 OAG that I used to reference this question is up in Fairbanks and I will be back there tomorrow night/afternoon at which time I will double check. The airline I found was different and did not operate out of EWR though it did operate 737-200s.