I think you'd love it here! What time of year were you thinking of going? HHI does have seasons (so cool in winter and not as much activity). Personally, I love what we call the "shoulder seasons" of April-May and and Sept-Oct (though I'd caution about hurricanes in Sept). Weather (except aforementioned hurricanes) is usually pretty nice and kids are still in school :)
I think you will find plenty of everything you are describing on HHI. The temps are wonderful right now, and the humidity is low. Hope you girls have a wonderful time!
Good advise from #2 & 3. HH is a match!
We are officially in the "off season" and went to the roof top bar at Poseidon tonight. It was pretty lively, had a fashion show going, lots of action. Pretty good for a "dead season" ;)
Hilton Head is an upscale but casual beach destination. You won't find blocks of fair food and tacky souvenir shops here. The beaches are beautiful, the people are friendly and the biking trails are awesome. Strict zoning laws keep the island looking pristine and uncluttered. During the next month or so there are some great festivals in the area celebrating food, drink, art & culture. You can also kayak, or do a dolphin or sunset cruise. No malls here, but many boutiques, outlets, and stores like Belk, Steinmart, TJ Max, etc. Restaurants galore and even the pricier places accept a casual dress code.