If you commit the aircraft to flying into a cloud, you have to guarantee that you can safely get it out of the clouds.
That's either by:
- an instrument approach to an airport, with the weather forecast to be comfortably above the minimum descent alt, or
- by flying the aircraft on a leg with the cloud forecast to be comfortably above the lowest safe altitude, so that you can reasonably expect to become visual while still safe from terrain and continue for a visual approach.
Option 2 requires an Area forecast, as you are considering flight in an area to become visual, not around an airport.