Keywords in that are "guidelines" and "recommendations"

This is what you've got to worry about, but worst case scenario you're out only $250 or possibly 90 days in jail:

Executive Order 2020-266, out-of-state people must self-quarantine for 14 days upon entering the state, before they go out in public/launch a boat:
"It is now necessary to restrict travel by residents of other states into Kentucky except in specific circumstances and to require residents of other states who travel into Kentucky for any reason other than those specific circumstances to self-quarantine for 14 days after entering Kentucky."

KRS 214.020 and KRS 214.990 - failure to self-quarantine is a Class B Misdemeanor. Generally, Class B misdemeanors are punishable by up to 90 days in jail and a fine of up to $250

https://governor.ky.gov/attachments/...-Emergency.pdf

KRS CHAPTER 214 DISEASES - LawReader