Not trying to be Negative Ned here, but your plebe may have only marginal control over his "best options" regarding his summer cruise. Our Youngster put in for San Diego but was assigned to Norfolk. The ship never left the pier the entire 3 weeks, and he was assigned to an enlisted who was separating because his job was being eliminated. He was done with "work" by 10:30 every morning. Not exactly a great sales pitch for the SWO community.
He also put in for YPs during third block but was assigned to sailing instead. The day he purchased his sailing supplies at the Mid Store, he received an email saying that due to safety concerns, there would be no sailing after all. He was assigned to summer school to take Navigation II (instead of having to take it his Youngster year, which actually ended up being a positive thing).
His situation had absolutely nothing to do with his grades (all A's and B's) or Order of Merit (top 25% of the class). It was completely random.
Bottom line is : Semper Gumby (always be flexible) and play the hand you are dealt.