As has been said, caulking around the frames isn’t likely to help at all. If you have the wood frame windows with the internal aluminum tracks as I do, there are basically 2 ways for the water to get in. One is between the metal frame and the opening. The only way to fix that is to remove the wood frame, then remove the metal frames, clean and rebed both. Depending on condition when these are apart like this it may be the time to replace the twin track frames. The other way the tracked windows can leak is if the drains are clogged or even not made correctly (as I found on my aft windows). For that, the lowest end of the outer track should have a hole from the bottom of the track to the underside of the exterior wooden frame. If you have wood exterior frames then you almost surely have these but they could be clogged or have been inadvertently sealed. It can sometimes also be helpful to have track drains from both the forward and aft ends of the track.
I found the best way to find the leak was first, make sure all the drains are clear. Then be on the boat during heavy rain and watch what is going on in the tracks. Are they overflowing or does the water just appear inside? Overflowing is a drain problem. If they are not overflowing but water is coming inside, then the seal between the tracks and the boat need to be redone.
In my case, I found slight leaking of my aft windows in heavy rains was caused by a slight forward tilt of the track bottoms. Since the track drains were only on the aft ends, the tracks were overflowing on the forward ends. I added track drains in the forward ends and problem solved.
Ken