Originally Posted by darthbimmer

I've done exactly that a few times already with Southwest when flying to the Caribbean from California. Just keep in mind that by booking two separate itineraries you are getting none of the advantages of having a connection. You'll have to re-clear security, you can't check bags through, and-- most importantly-- if anything happens with your first itinerary that makes you unable to be there on time for the second one, the risks and costs of dealing with that are all on you.