Location options for boyfriend's checkout dives....

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If it's only 4 nights, I would choose something close, like Key Largo or Turks and Caicos. Key Largo has excellent sites for beginning divers.
 
... the trip length would probably be 4 nights, and we would prefer not to have the airtime be longer than 7 hours ... warm since we are also looking to escape the cold for a bit

AFAIK on Bonaire, Curacao, and Roatan (at least) package deals are 8-9 nights. Plus, you may get the time actually in the air down to 7 hours but total travel time is going to be "if you start really early, you might get to the shop before it closes and have your checkout dive on the same day -- but I wouldn't count on it".
 
The FL Keys come to mind for a quick certification oriented trip, but if you're looking at going very soon the water may not be as warm as he'd like, or even the air if you're unlucky. Same with the Bahamas.

For a short trip obviously closer is helpful and non-stop better. I think places like Bonaire, Curacao, Roatan, Belize are great for checkouts but getting to these and really so many of the better Caribbean dive destinations from Boston requires connections that can make for a long travel day. I'd focus on closer/mainstream places like Grand Cayman, maybe Provo, maybe even St Croix. Start poking around at flights and see where you can get the best schedule. Flights also may also depend on when you go, since some flights may only be peak season or only certain days of the week. Since Saturday-Saturday travel is popular there's often more flights then but a 4 night trip doesn't allow you to do Saturday both ways either.

You might also look at Aruba again. While further, it's such a popular tourist destination with lots of flights you might still be able to work a relatively cheap/quick trip. Diving not as good with as many options, but likely to be way easier to get to than Bonaire or Curacao next door.
 
I did my checkout dives in Negril Jamaica. It was great. I dove with Sun Divers. I think they will only accommodate up to about 6 divers on their boat. It ended up being a private class for me. The diving was good. The staff were great. They also dive a little earlier than the Sandals and Beaches resorts nearby so we were leaving the popular sites before the big groups arrived to chase away sea life(we dove along side a small pod of dolphins for 20 minutes before a resort boat arrived and the animals disappeared.)
I also know there was a couple from the USA there for only the weekend. I can't remember where they were from but want to say northeast coast somewhere.
 
A location that doesn't seem to get much respect, but might fit the bill perfectly: Cancun (or Isla Mujeres).

I did a short trip (5 nights) out there last summer, mainly for the whale sharks, but did a few dives, too. Warm water, good vis, shallow dive sites with short boat rides, nice marine life (I had better turtle encounters here than in Cozumel or Belize. Obviously, ymmv.). There's also the nice underwater art museum, which I really enjoyed. And at least when I was there, very calm seas and mild currents. And it's such a mega-tourist-destination that there are tons of flights from all over.
 
Surface temp for Key Largo right now is 76 degrees. The "at depth" temps will be several degrees cooler.
 
I recently went to FL for a refresher dive. South Florida Diving Headquarters is located just north of Miami at Hillsboro Inlet. While the dive operation was great - we ended up doing a drift dive - which I was not expecting. (Very rough waters). I would not recommend diving in the currents we were in for a beginner. It most likely was a seasonal thing but I would check out the dive conditions before signing up anywhere. Being from NE - I thought the waters were warm for December in FL. If you can swing FL, there are lots of dive operators on the Keys and direct flights from NE.
 
I would checkout Cayman, Jamaica or Provo. The U.S. Virgin Islands is another option. The Florida keys maybe your best choice given the length of your trip.
 

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