I started by making a tentative schedule to share with My Team, picking starting and ending and all points in between. I analyzed transportation options, schedules and costs, and tweaked the schedule to minimize travel time and maximize tourist time. And I started scoping out flight options to share.
I went through several iterations of tweaking the schedule -- based on good train connections, availability of good AirBNB bookings close to the train, things to do, diversity of locale. And I ended up with what I believe is a fun, efficient, and comprehensive overview of Tuscany and the central coast.
I added days onto the beginning and end of the group trip for me, myself and I (it is my vacation after all) and I booked a really great flight for myself through Milan.... JFK <> Milano $850. Duh.