The most distinctive city in America, and the easiest to plan badly.
This is a shape, not a schedule. Each day has two anchors and a lot of slack, because 3-day itineraries that book four things a day fall apart the first time lunch runs long. Move things around freely — the neighbourhoods are grouped so that walking between stops actually works.
The city runs on booked tables and shows, and the best restaurants take reservations weeks ahead. Split the bookings across the group rather than leaving it to one person, and keep them all on one shared plan so nobody double-books a night.