spyglass is nice, if seafood isn't your thing then i'd recommend the white lion in arreton, they have superb food but unless you sit outside i don't think they'll allow dogs, i'd imagine that's pretty much standard policy everywhere...
depending on what you're interested in there are a few places to see, if you're into the touristic things then alum bay and the needles is suitably quaint, as is godshill. if you're into views then i recommend ventnor down, mottistone down and culver down, and make sure you visit the car park above black gang chine, on a clear day you can see all the way to the needles
let me know a bit more of what you're looking for and i'll see what i can think of...
oh, and grinch, i've lived here so long i've forgotten how long it was, somewhere in the region of 15 years now, eek, my toes are webbing as i type this
