I checked SJU to EIS airfare the other day for early June 2016 and it was running $600 pp. I was shocked.

I was trying to get the most bang for the buck when I put my first trip together in 2014. I found Pro Valor to have very good rates. We were down around 5k for a 44' cat without AC. I took ASA 101, 103/104 before booking the trip. They booked me a checkout captain for the first day since my classes were on a mono. You might look into this as an option for you. THe biggest value I found on the checkout captain was that he was an excellent teacher. I never felt like I was being quizzed or tested. After he verified me, he then spent the rest of the time with the crew teaching them what to do while I was sailing. He worked with me on picking up the mooring ball, then he worked with them, then later he worked solely with them on raising and lowering the sails and then what to do while tacking, etc. I went over my itinerary with him in detail and he had some great ideas for me to ammend our plan. The whole thing was a great experience.

EDIT: We booked 10 days for 7 in early June and $4500 on the boat in 2014