Had a great, but quick week long charter. It was nice to see things opening up again.
I flew JetBlue FLL - SJU - EIS codeshare with Silver. the trip down was routine. The trip home, not so much.
The Silver flight from EIS to SJU was 2 hours delayed. I left 2 ½ hours to connect. The Silver rep knew that when he checked me in at EIS. He couldn't find another flight that day so booked me the following day and provided me with an overnight hotel stay at the "SJU Airport Hotel". This hotel is actually built in what seemed to be an unused/abandoned part of the SJU airport. I needed to walk through multiple slumbering homeless making my way from the baggage claim area to the hotel. It definitely felt like a "lock your doors tight" kinda place and most of the folks there had airline vouchers in their hands.

I know that it's not theoretically necessary to use the Puerto Rico travelsafe portal when just transiting, however, you never know when your simple transit may turn into an overnight, especially with Silver. Fortunately, I registered on the portal prior to departure just to be on the safe side and used a randomly selected airport hotel for my place of stay. Glad I did that as it just saved another hassle with whole travel experience.

Not sure if this is typical for Silver since I generally use Cape Air. Next time I'll be more specific with them when I book.

Also, as a side note, the JetBlue app would not allow me to check in nor could I check in on their website on my phone. The silver rep was unable to print a JetBlue boarding pass, so I would not have been able to just transit the SJU airport even if the Silver flight was on time as I didn't have a connecting boarding pass in my possession.

Although it was a frustrating 2 day journey home, it was still worth it.