Ventnor is lovely. Steephil Cove reached via the Botanical Gardens in Ventnor is a hidden paradise. Shanklin Chine is very very pretty, you have to pay which is a little cheeky but worth it. At the bottom of the Chine is a pub called Fishermans Cottage right on the beach.
Loads of places to eat, can't remember them all but you won't have a problem finding somewhere decent.
Carrisbrooke Castle is a great day out. We loved Blackgang Chine theme Park too as it has a nostalgic feel to it and is in a beautiful setting.