I hope to hear back with some suggestions!
Thanks so much
-Cheyenne
Where in New England are you? Jet Blue (and others) have pretty good deals out of Boston to the Caribbean. I'd be all over that!
Consider a liveaboard - between the crew and 11-17 other divers you'll have plenty of people to buddy-up with. Liveaboard (Cayman Aggressor) was my first real dive trip after getting OW and AOW and it was a great way to get lots of dives under my belt in ideal, easy conditions. Plus, the need to only set your gear up once for the week is nice, too!
Key Largo, etc are fine... assuming you don't get blown out, which often happens.