The 1935 Labor Day, 1960 Donna and 2008 Fay are the closest analogies I can find for a Hurricane going up the West Coast of Florida.....and that track S of PR.
Only Fay crossed Hispaniola and the narrow part of Cuba into Havana.
The 1935 Labor Day was the only one I have that literally raked the W Coast of Florida.
Donna the only Cape Verde, but like the 1935 Labor Day, going N of the Greater Antilles.
Correct me but I don't find a hurricane approximating Isaac's path.