[Briguy]

Billybob gave pretty good advice. However I would drill the holes out with a 1/4 bit, glass from the outside and then take a bit of resin and pour or inject it into the drill hole from the inside and let gravity do the work. It will be fixed forever. I would never ever ever fill in a FIBERGLASS hole with a caulk. Fiberglass and resin were made for each other. Polyester resin is cheeper and should do fine since that's what the boat was made with.