I have done this a few times now - I have flown Jet Blue or Southwest to SJU from Florida. I have done both checked and carry-on. I have flown InterCaribbean and allowed 2 hours when I had a checked bag — if it is not a code share (mine were not), I collected my bag and rechecked it an hour before the InterCaribbean departure, which is when their gate typically opens. Have not missed bags yet. I also have Global Entry so I am guaranteed TSA-pre which helps with timing....

I think we’re going to go the ferry route this year, depending on pricing - I kind of like the whole Petit Pump experience