We're going the Montessori route so hopefully I'll be answer this soon. I've been very drawn to it due to the multi-age classrooms, focus on child-led learning, and the calm environment (DD would probably loose it in a play based classroom if there was a lot of noise and it was chaotic). I also love that they work with the child to be responsible for putting away their own things, prepare their own snacks, etc.

That's what I love about it... but will it be a perfect fit? Only time will tell. DD gets VERY freaked out when her hands are dirty but on the other hands loves to touch things so I'm guessing stuff like the sand paper letters will be a big hit for her (she also seems to focus more on writing than reading so again it seems like it might be a good fit). Our hope is that it will help with her fine motor skills since those always seem to be a bit behind the rest of her skills.

I will say, though, that we looked for a Montessori school that appears to be more focused on being a child-led environment than one that has to have everything in a certain order. So maybe it's not super strict in that sense?

All Montessori schools are not created equal so just because this one is a bad fit doesn't mean another wouldn't be too (I can't tell you how many times I've heard of families switching to a new one and loving it but hated their first or second tries).

Also, have you tried talking to the teacher about your sons problems at the school? Is there another classroom that he could switch too? Have you viewed the gifted school? Have you asked him what he thinks about switching schools?