This is a VERY high end shopping area, like Rodeo Drive. Escalators, fountains, Tiffany's, etc. But they do offer affordable options like ABC stores and one of a kind businesses that aren't off the map price wise. There is definitely something for everybody. And lots of good food in open air bars and restaurants!
It is a very beautifully designed area with lots of comfortable seating that is intended to promote hanging out. In the center of the mall is a stage and one evening we were passing though, they had some great entertainment with a Hula dancer. Talented musicians. Combined authentic Hawaiian songs with some others that included songs by Tracy Chapman and Norah Jones . People began gathering and it was a very family friendly atmosphere. Little kids were dancing and the whole vibe was great!
The reason I rated it a "4" is that most of the shops are places I could not ever afford to shop. Wailea is one of the most expensive areas on the island. I remember 25 years ago when that shopping center was very primitive and undeveloped and a Hawaiian lady was doing Hula lessons with kids on the shopping center lawn amidst the mud puddles. I only stay in Wailea because I am able to still stay in my ex husband's condo for no cost at this point. But Wailea itself is gorgeous. Highly recommend visiting this shopping center.