That place is amazing.
It's been three or four years since I last cycled over there and I'm amazed by the quality of the roads in the west of the island now. Military Road has been resurfaced, but so have the back lanes just off it. Beautiful tarmac worthy of Majorca. Not a single close pass in a week of riding. Really challenging rolling terrain, and Ventnor must have some of the steepest short sections of road in the country (western exit to the prom in particular). Strongly recommend heading one road inland from the Military Road because it's better protected from the wind and much more engaging to ride - constant gradient changes.
Has the Tour of Britain ever visited? You could build a fantastic stage over there, and being September the massed hordes would have left. Possibly not enough miles available without disrupting the whole island I guess.