Jason, we are doing the same dance in SJU that BVIslandGirl describes, coming into SJU on one airline (Jet Blue in our case) and then jumping on a separate booking for InterCaribbean. The difference is, we will only have a scheduled layover of just under 2 hours in SJU (one hour 50 minutes). Assuming no flight delays, think that's enough time to collect bags and get checked into InterCaribbean? Thanks for the advice!