You are somewhat confused about "the experience of weightlessness", relative to how we should say whether a person is subject to the force of gravity, or not.
Now, first off:
If we look into general relativity, the conception of "force", in particular gravity, is radically different from that within classical mechanics, but YOUR confusion can as easily be explained in terms of classical mechanics, so that is what I'll do:
When we "feel" our own weight, what is the ACTUAL force we are sensing?
If you simply stand on the ground, it is the NORMAL FORCE acting from the ground on you experience, that you think of as your "weight" (it is oppositely directed to gravity, but of the same magnitude).
Note that if you are in an elevator accelerating upwards, you will FEEL heavier (you feel a stronger push on your feet), although gravity hasn't changed a bit, but the normal force acting upon you has increased.
Are you in FREE FALL, only gravity acting on you, you will feel weightless.
Astronauts and the moon is in FREE FALL around the Earth (the moon keeps missing its target, fortunately!)
But, free fall is a situation in which you, as emphasized are under the influence of gravity, which in the classical mechanics point of view means you are subject to an external force, making your motion deviate from that of following a straight line of motion. You are following a determinate orbit, not floating "aimlessly" around.