Consider the College of William & Mary in Virginia for History major.
Wm. & Mary also has a joint degree program with St. Andrews in Scotland. Students do first year at one school, second year at the other, and then student & counselor decide where to attend in the third & fourth years. Must spend two years at each school. (First year is done at the school through which student applied to be in the joint degree program. You get one degree stamped by both St. Andrews and by the College of William & Mary.)
Since you like sailing & would enjoy a merit scholarship, the College of Charleston Honors College (700 honors college students on a campus of 9,000 undergraduates = the best of both worlds) may be an interesting option. Arts Management major. One of the best sailing teams in the USA.
Part of the campus of Davidson College in North Carolina is on a beautiful large lake. Strong academics. (Somewhat similar to Bowdoin College.)
If you really want Amherst, Bowdoin, Middlebury, or Williams College, then you should consider an ED application. Williams College has a strong Art History program (Williams College Museum of Art).
Are you an under-represented minority (URM) ? First generation college student ?
Definitely apply to SUNY-Geneseo & New Paltz as safeties.
You might like Wake Forest University–certainly preppy. University of Virginia also.