The shaft length is determined by the boat and the motor mount so that the prop is sufficiently submerged to propel the boat. Where the boat is sailed is inconsequential.
Different point of view.
The 20” on a properly located bracket can be low enough to sufficiently propel a boat on flat water such as on a smaller lake or bay.
Move that same boat to a much larger lake or bay with lots of power boat wakes and or large fetches producing large wind driven chop and the 20” shaft now will spend some time out of the water.
That’s where the 25” shaft would be more appropriate.
For the Chesapeake Bay I’d go with the others who suggested the long shaft.