Seriously depends what kind of holiday you're after. PM me if you like and let me know what kind of holiday you're after.
Frequent visitor's opinion Have family over there, just on the edge of Newport, so we go over at least a couple of times a year. It's a pleasant enough place except for the roads which are not the best. To be honest though there is nothing much there that you wouldn't find in other south of England resorts, so the extra expense of getting there has to be a consideration. That short crossing is one of the most expensive ferry trips in the world, if you take your car in the summer. I will be there 9-11 June for the Isle of Wight Festival which is a huge music event. Coldplay are topping the bill on the Sunday. You might like to avoid that time of the year unless you want to go to the concerts of course. The island is swarming with people for that. In summary - nothing against the place but nothing special either. The beaches are nice with safe bathing for kids if you have some of those.
RE: Frequent visitor's opinion I have to step in and defend it a little. The worst way to experience the Isle of Wight is by visiting with people that live here. I include myself, but people who live here take it for granted. There are some absolutely stunning areas of beauty, it's steeped in history, superb beaches, both commercial and quiet. It has a much more relaxed feel to it, if you compared it with popular south coast resorts like Bournemouth and Brighton. It has very traditional country pubs, incredible views, 3 prisons and gays. The ferry price is ridiculous though, £25-£35 return in the winter compared to £100+ in the summer is just robbery. Cowes Week is fantastic.
No argument with any of that Rick I suppose someone going there for the first time would think it was fantastic but I suppose I have got a bit blase about it over the years, in the same way a resident would. I lived for many years in and around Salisbury so couldn't see what was so special about the island scenery compared to similar in Wilts, Dorset and Hants for example. Having great beaches is a big plus obviously, unless you happen to be undeneath a car when one of the idiots runs his vehicle off the edge and onto the sand (amazing how many times that has happened!)
RE: No argument with any of that Rick I'm the same though, living here is very different, I spend my time whinging about roads and travel costs and all the usual stuff. I barely go to the beach any more and I certainly don't do any walking, but when someone visits for the first time, you show them round, you take more notice and it's a great place. People generally fall in love with the place.