AA 1688 then AA 1689 at Charlotte
Boston → Charlotte → Sarasota
Timetable, Charlotte time
10:39AA 1688 from Boston at the gate
08:20AA 1689 to Sarasota leaves the gate
21 h 41 apart on the timetable, overnight
AA 1689 leaves 21 h 41 after AA 1688 arrives on the timetable: more than half a day, so not a connection we count.