Just got back home from my last flight of the year! I don't fly as much as some people but more than most, over 100k last year. 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. We have flown down via United, Jet Blue (not a fan but would like to do Mint sometime), US Air, Delta (also not really a fan) and of course AA (I will not fly Spirit). I at one time or another had status with all of those minus Jet Blue. I like AA, and they are a partner with Alaska which is where I keep my status as Alaska Airlines has the best Frequent Flyer program and once they started flying east coast as well I moved most all my use to them. Still fly Delta at times, have not flown Jet Blue or United since Covid. All the problems I have had on AA are no worse then the issues I have had on Delta or United and I would say my worst experience ever was on Delta via ATL.

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. We really like the TWA Hotel at JFK but that is usually a bad route for us, the DFW option offers the Grand Hyatt which is in my top three airport hotels so we do like that option. 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.

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.

I suggest to anybody to work on gaining status in what ever hotel or airline program works for you, Alaska works well for most my travel and Hyatt has easily the best hotel loyalty program in the industry. I travel for business but it is also a hobby of mine, I actually enjoy the planning and working to get the most out of my travel benefits. I study it, create spreadsheets to manage values from which credit card to which hotel or mileage program to use. MJ just knows all she has to do is show up and I have it covered.

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