I grew up on the Isle of Wight so in addition to my above link to the Freshwater Beach park in Dorset I can offer the following info on the Island.
Ventnor, pretty but steep and exposed.
Sandown/Shanklin, best beaches, most hotels, most amusement arcades etc.
Ryde, er you can see across the water to Portsmouth, it’s got an ice rink that may or may not be open when you get there (the parent company now has a winding up order against it).
West Wight Freshwater/Yarmouth, scenic, historic but very quiet, retirementville.
Biggest tourist attractions:
Robin Hill Park, mainly animal based with some good activities for school age children.
Blackgang Chine, rides, loads of displays, looks great when illuminated in late summer evenings.
Carisbrook Castle, plenty of history.
Sandown Zoo, lots of tigers and snakes.