Hilton Head is incredibly developed.From a cold, wet East Anglia in England, I can see one or two pluses.
In the middle of the summer Hilton Head is congested. There is a lot of traffic, even traffic jams. Not what most of us want on vacation. Even in the off season there is a good bit of traffic. There are literally hundreds of restaurants. Many (perhaps most) of them are lousy; fortunately I know enough good restaurants.
If shopping is your thing, Hilton Head Island and its neighbor, Bluffton, which is just across the bridge and must be traversed to drive to the island, will be just the ticket. Outlet malls, upper end stores, specialty shops, car dealerships. Etc. Etc. Etc.
For someone like me, a non-shopper, the shopping opportunities increase traffic and congestion. There's no shaving supplies store, but perhaps our friends in NYC will open a branch of Pasteur Pharmacy. Now, that would be a draw for me.
Many people retire to Hilton Head and Bluffton. It's a booming place. Last week I spent an evening with a realtor who said there is a big sellers market in real estate at the moment. I know several people, not retired, who've moved there to find good jobs and raise a family. As you'd expect real estate is out of sight expensive.
The beaches and other natural features are great of course. There are many golf courses for golfers and tennis courts for tennis players. There is a lot to do at Hilton Head. The weather at Hilton Head is much like the weather where I live. Hot in the summer. Humid. Reasonably mild in the winter. Great in the spring and fall.
My idea of a great beach and a great barrier island is a place a whole lot less developed and vastly less crowded than HHI with pretty much no shopping beyond the basics and nothing to do except enjoy the beach.
Most folks around here, including me, like to go to Hilton Head. Most of us think the best time to go is May or September or October. May in Hilton Head can be glorious!
Don't get me wrong. I love going to Hilton Head. Sometimes it's perfect.