sorting out a long college list

You don’t need to find more safeties, unless you are hoping to get a large merit award. Get rid of all but two, and maybe even one is fine. After all, by definition a safety is a school you will certainly get into, that you like, and is affordable. You seem to like LACs and that kind of vibe, and you seem to prefer colleges offering a classic liberal arts experience. I think you’re fine for safeties with Wheaton and Geneseo.

Hamilton and Colgate are reaches. They aren’t as selective as Brown or Dartmouth, but they are not really match schools with your GPA and test score as it is. I see nine reaches on your list. Curious if you’ve considered Bates. It seems to fit your criteria and has a sailing club.

I think you should do some serious culling. Eliminate those that aren’t affordable. Eliminate those you don’t have genuine interest in. Try to limit yourself to maybe a few high reaches, a few lower reaches, a few matches, and one or two safeties. 10-12 is plenty, though so many students apply to many more. I think this coming year especially, colleges will look for signs of real interest. Visiting may not be possible, so sing up for email lists, request interviews, and complete all supplemental essays and/or short responses.