I have to visit these high schools around Boston every spring. Can Google maps optimize the route for least miles traveled, or convenience etc.?

Here is the map with 19 stops:
http://maps.google.com/maps/ms?hl=en&ie=UTF8&msa=0&msid=115004805904883153148.000469290f4747a0e82f2&ll=42.376807,-70.911255&spn=0.988094,1.757812&z=9

No, it cannot optimize over multiple stops. That would be a great feature for us users, but it would require much longer to run through all the permutations (factorials). We have expensive routing software at work that creates and optimizes routes (with many other parameters which help reduce the # possible routes). If Google were to release such a feature, I think it would hurt a lot of other products that offer similar features. And since such a feature would be used heavily by businesses (sales, customer service, etc), it would probably be a good candidate for a fee-based premium version of Google Maps – maybe with the premiere business apps edition.

My guess is they either have a dev version of such a feature or are working on one. But, since it would be CPU cycle intensive to run, it probably doesn't make financial sense to release it without a subscription or fee.

I just found this site: http://mapcircuit.com/. Looks like it does what you want. It even uses Google Maps. Looks like it is free for very short routes, but charges beyond that.