I’ve heard that Choate and Hotchkiss have a more rigorous academic program, but I’m sure all boarding schools are great in that sense. Also, although Taft may be a notch lower, I think that a school in which you are able to be on the top of the class is better than failing at a somewhat “better” school. If you would like to know what languages you can take, I suggest you visit the Taft homepage and search in the academics catalog. Also, I’ve heard that Taft does not accept students with a ssat percentile lower than 50%. You can be on Varsity, JV, and thirds for some sports as well.
Although taft has a “jock school” (I’d prefer “sporty”), it was proven untrue a few years ago, but you don’t seem to need to worry about that!