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@moth
I rode the randonee last year and the view out over an empty cloud-mottled sea from the road along the hill-top above Ventnor is a memory that sticks with me. You'd probably get some more memorable views from the chalk spine along the middle of the island.
No idea if old fortifications interest you, but it might be fun to explore some of the island's Palmerston forts http://en.wikipedia.org/wiki/Palmerston_Forts
and there's Carrisbrooke castle above New Port.