Hurricane warnings have been hoisted in the face of Isaac in Florida, as well as tropical storm warnings blanketing Cuba. Isaac has just moved off of Haiti and appears to be heading northwest, towards the Florida Keys and the Gulf of Mexico.
If Isaac makes landfall on Cuba, it appears to be brief, and only a slight change in storm strength would likely be observed. However, if Isaac plows into Cuba, which is unlikely, the tropical storm could have issues with keeping itself together.
From this viewpoint, it seems a brief landfall on Cuba is likely, but nothing major as far as going through much of the country.