The problem with going to the east coast to a city like JFK and then out is the cost, we pay not much more for a ticket than somebody that has the direct flight from the east coast, so add a RT to the east coast and my cost goes up significantly. I have over the years done trips east and then down, pretty much you name the route to SXM and I have done it. Via, JFK, EWR, ORD, LAX/SJU, ATL, PHL, CLT, IAD, MIA and with many stops along the way.

I would add that the chance of bad weather in the winter keeps us from choosing northern east coast hubs

I wish that Miami had a better airport hotel as we do like leaving SXM and just getting the first flight out of the way and then relax but that airport hotel is terrible and we don't like to have to shuttle or cab/uber to a hotel.

This is disheartening to hear. We are overnighting in Jan at the Miami airport hotel.

We have made the entire trip in a single day and are actually scheduled to do that in March but that is a tiring trip and often results in a missed connection which really screws up the balance of the trip such as seat choices.

Been there, done that. Never again, we will overnight on our own terms!

We also almost always fly in the big seats, just too far for a guy my size to sit in coach for that long. Everybody spends their money in different ways and for me that is an easy spend.

Agreed, especially for those red eye legs!

Enjoy the trip, you never know when it might be your last.
Todd