Ventnor really does feel from another time. The individual high street shops (with refreshingly friendly staff), some quite unique, steep streets and great beach give this town some individuality. While suffering like many tourist driven towns, Ventnor is still investing in the harbour with the excellent addition of Blueocean Quay, home of Goodman's Bistro. New toilet facilities and a revamped paddling pool make this a great spot to admire the view and entertain the kids. Pub food is hit or miss, but the Spyglass Inn deserves special mention for the location - you couldn't get any closer to the sea without getting wet! More variety in the town centre.
There are the fabulous Botanic Gardens, which even my four and six year old loved. The mostly sandy beach is a managable size (a good thing if trying to keep an eye on the kids) with beach huts and deck chairs for hire. Plenty of ice cream and bucket and spade shops too. I like it so much I bought a holiday home there!