assuming lokcs are open (one or more are sometimes closed for maintenance in summer), going across isnt a problem. I did it 2 1/2 years ago, no bridges to worry about. it's a very viable option...
randy, what's the coverage area on your policy/binder ?
staying for a while over cuba will slow the storm intensification but NHC often under estimate intensification... we've seen many storms exploding in the SE gulf/FL straights...