Just booked JFK to BON flight using the new JFK flight to San Juan that gets into San Juan at almost 5 PM which makes the wait for the 7:30 BON flight reasonable. Considering that JFK flights are often a hour late getting in, that makes the trip to Bonaire almost easy. The best part is that the plane leaves JFK at noon which makes it easy for New Englanders and Shelter Islanders to get to the plane without an overnight stay on the way. Peter

I'd be hesitant to do that.

There are SEVERAL airlines that can we can take from BOS to SJU on a daily basis.

But there's only one airline (AA) that flies SJU-BON and they're down to just a few days a week now.

Too many things can go wrong with this approach

I failed to say that all flights are with American Airlines. I agree I would not use different airlines as any delay would be a big problem. Peter

I would make sure that you have your boarding pass for the Bonaire leg in hand when you check in at JFK. If AA says that you need to get it in San Juan, that is a red flag.

Peter-
I was tempted to take that route (well, BOS-JFK-SJU-BON) after they changed my flight (6:15 am) and gave me an 8.5 hor layover in SJU. But i decided to live with the layover and go to a hotel beach because I didn't want to take the chance of missing the flight to BON if one of the legs is delayed. I'd still have to leave just as early (as I start from Nantucket), so I dont really gain anything. But good luck to you. I hope it works out!

Peter - hate to dampen your spirits but with your late arrival to SJU, you also tempt fate that your luggage will be some of the luggage that American Eagle often has to leave behind because of plane weight restrictions. My husband and I leave from JFK also but chose the early morning flight so hopefully our bags will be ready and waiting to be first on the Bonaire plane when ready to load. We plan to go to the beach during our layover in San Juan. But either way, I plan to pack our carry-on's with the things we can't do without because with the new plane schedules it might be 2-3 days before a late bag arrives.

We always cary on all important items(bathing suits, regulators, masks, BCs, fins and boots) the rest can be done without for 2 days. We will be in San Juan 2 1/2 hours with America Eagle boarding passes from JFK at 10 AM. For 3 years we had the long wait in San Juan and I'm feed up with it.