actually...elevation plays more of role, more like a tremendous, gigantic role... distance island, believe it or not, is less and inhibitor than taking a circulation field and attempting to impinge it against a wall of mountains that pokes up above the mean boundary-pause... In the end, loss of lower boundary layer coupling with the heat content of the SST is will is a factor, too, but in terms of distruction of established mechanical wind momentum, mountains of more important.

the boundary-pause is the level where the atmosphere becomes less influenced by friction with the land and what is refered to as Eikeman Layer turbulance in the pbl its self. Above about 3,000 to 5,000, feet depending on your thermodynamic values and advection parameters (i.e, strong latter pgf can help in establishing a deeper mixing level and a huge potential instability will also turn the boundary layer over and mix to greater heights), is where the turbulence of the boundary layer gives way to gradient wind. If a topographical obstruction to wind field extends to a meager 2,200 feet or so, then this does not imply enough vertical extent to inhibit the entraining air flow. It will be lesser inhibited along the established angular momentum and the circulation of the system may just run right over the top and barely be touched... . Cuba does not offer this disruption. There has been extensive study about tropical cyclone interaction with Cuba; I'm not making this stuff up...

Yes, I have a formal degree in Meteorology..