There are some VERY good high school posting on the Web here, no disrespect to you, the kids who play for you are very fortunate!
Last night my 27yo stopped by to pick up the grandkids who were here to redecorate the house. I figured HE would have chosen High school as the best memory over travel because he was more of a social butterfly and had many friends at school, they had a very good team, great fan support and a great Coach. To my surprise he said as well that Summer was easily his choice of great memories and enjoyment. The kids he played with in the Summer had the same goals and were more like minded than the kids on the school team.
High school baseball here is a great opportunity to get conditioning in and reps, interact with various personalities and skill levels and work on your game, and if you're lucky enough to have a great coach your game and life direction can get a big boost. Either way the high school baseball experience will teach you about life and help you grow as a person. But as far as enjoyment and memories, both my sons chose Summer in a landslide.