If you want a school like Milton Academy, start them out in KG or primary grades where there are more spots availale. Be willing to foot the bill for private school to get them in early. We had a plan to send our kids to BS in 9th, but by the time they applied, there was only something like 1 male and 1 female spot available in 9th grade at MA. Look at the schools and if you want a private day school, start 'em early when more places are available.