Pilots who live in Florida, and especially on the west coast of Florida, have this problem. Its called the Gulf of Mexico. Nice beaches and all, and warm for nine months a year, but if youre going anywhere west of about 85 degrees longitude, youll have the argument with yourself about cutting the corner across the Gulf.
This is a companion discussion topic for the original entry at https://www.avweb.com/flight-safety/technique/the-overwater-argument