It’s a great ride, but I’d rather avoid the chaos of the event. As a bonus I’m sure you get dragged along with the excitement.
As crazy as it may sound, I've only been to IOW once in the last ~35 years of living in Southampton and that was a week's holiday back around 2006 iirc, long before I would have thought about riding!
Ventnor esplanade to the top of Down Lane was on my "to do" list in recent years, it's a bigger climb than Sheet (Village St) to Warren Corner near Petersfield at ~2 miles of ~10% average, maybe I'll do it on the ebike sometime.