Colby could check a lot of boxes in terms of culture, having a museum, etc. But alas, not sailing team. A nice boathouse on a beautiful lake, lots of kids who sail, but AFAIK, no team.
Tufts has an excellent sailing program. Has always attracted a lot of prep school kids but I would not describe it as “preppy” (realizing that term seems to mean different things to different people.) A bit bigger and more urban as n than many of the other schools mentioned here.
You may want to try to separate out gotta have, wanna have, and would be nice. As well as no way!