I am always of the opinion that you should go with your heart, if your inclination is strong, and the educational quality is not dramatically out of whack. So if after visiting both schools, you really feel strongly like Kenyon is the best place for you, you should go there. However, I do believe that while your assessment of Williams’ strengths are dead-on, its perceived weaknesses are not true concerns (especially relative to Kenyon).
I visited Kenyon / Williams and applied to both long ago, and both were among my top choices. I do think there is a significant difference in the overall intellectual level of the student body, and ultimately in post-graduate opportunities. If you (just to pick an example I’m familiar with) look at the top five law schools, they all will typically have somewhere between 5-20 Williams grads in their student bodies, while they will maybe have 1 or 2 (if that) Kenyon grads. You will probably have to do very well at Kenyon to have the same opportunities you would have just kind of being middle-of-the-road at Williams, but on the other hand, if they are giving you merit aid, the expectation is probably that you WOULD likely do quite well.
I, too, found Kenyon very charming. That central path is spectacular. And literature / writing is a huge strength there (it is also a strength at Williams, but one of many, while I remember getting the sense that Kenyon placed a special emphasis on those departments). It does have a very bucolic, lovely campus, and the town is adorable. My concern was that, even compared to Williams - itself quite isolated - that Kenyon / Gambier was just TOO small and insular a community, and too isolated from the real world. Williamstown at least has a few streets and a pretty good number of commercial institutions, a small movie theater, a few bars, etc. Gambier (at least based on my memory), almost none. There is also the Clark Art Institute and North Adams (which is rapidly developing in interesting ways), MCLA and MassMOCA nearby, so there are other major local institutions beyond just the college, whereas Gambier was basically Kenyon and that’s it. Plus, only three hours to New York and Boston, 5 hours to Montreal, so easy to get away for a weekend. And also the student body was substantially smaller at Kenyon, and that makes a difference when you are dealing with schools that are small and insular to begin with. Williams also is substantially more diverse by basically any metric. To pick the most glaring example, only 18 percent of Kenyon’s student body is domestic students of color, and only 4 percent international. Williams has 40 percent domestic students of color plus 8 percent international, so a dramatic difference.
My sense of Kenyon was that it would be an incredibly comfortable, lovely, cozy, charming place to be, but wouldn’t challenge / push me in the same way, nor expose me to as many diverse experiences and perspectives, as Williams – which is still plenty and cozy and charming, by the way! Williams is a very, very intimate place, I think with these schools, the concern is more feeling TOO cocooned over time, rather than insufficiently personal / intimate, and I felt that Kenyon (even for someone who wanted a small, intimate environment) would feel a bit stifling over four years. And I would also not be concerned about the level of intellectualism in the classroom at Williams – Williams is a VERY intellectual place.
The money is a real consideration. If you dramatically preferred the Kenyon environment (and I’d second others by saying that admissions salesmanship isn’t really a basis for judging, you need to go on campus and meet students and/or recent alums if possible) AND they are giving you 20k more per year, picking Kenyon certainly won’t be a mistake. But, if your concerns come down to, I’m not sure that Williams is sufficiently intellectual, or it is too athletic or pre-professional, or it won’t be a comfortable environment for learning, dismissing Williams on that basis would be a big mistake. Because some of your concerns about Williams seem, to me, to be focused on what are actually some of Williams’ biggest strengths.