Excellent questions by Rich and very detailed, informative answers by Sage. I am planning a late spring 23, 7-9 day trip somewhere. Coz has been very good to us over the last few years but this kind of first hand info into P.R. makes me think. Sage, can you expound briefly on your flights to and from P.R.? I consistently see decent priced flights into San Juan from Ohare but the times in and out are less than desirable.
We flew out of Indy. Booked tickets late last summer when we saw some cheap prices and the flight changed about 6 times from that time. Our flight left Indy around 6am, layover in Miami, and into San Juan around 3pm. Flight out was at 2pm, layover in Philadelphia, into indy around 9. We're pretty used to layovers no matter where we go.
I don't think you'd regret this trip at all and if you can 9 days I'd do that.