Wailea, Hawaii
Both South Kihei Road and Pi'ilani Highway end on the southern fringes of Kihei. The only road south, branching off Okolani Drive halfway between the two, is Wailea Alanui Drive, which becomes Makena Alanui Drive after a couple of miles. It's forced to run several hundred yards inland by a sequence of half a dozen colossal resort hotels, constructed on a scale to rival any in Hawaii. Neither WAILEA nor MAKENA is a town as such; were it not for the resorts, the names would not even appear on island maps. The only shops in the area are congregated in the very upmarket new Shops at Wailea mall, whose target audience can be assessed from the presence of Louis Vuitton, Cartier, and Dolce & Gabbana stores.
Until the 1950s, what is now Wailea was just barren oceanfront acreage belonging to the 'Ulupalakua Ranch. It was then bought by Matson Cruise Lines, who planned to turn it into the "City of Roses," but nothing happened until control of Matson passed to Alexander & Baldwin in the 1970s.
Makena, which segues imperceptibly into the south end of Wailea, was developed even more recently: its first hotel appeared at the end of the 1980s. For a period in the late nineteenth century, however, it ranked as Maui's second port after Lahaina, thanks to the comings and goings at 'Ulupalakua Ranch, just two miles higher up the gentle slope of Haleakala. These days, in the absence of any direct road, getting to the ranch requires a forty-mile drive.
Wailea and Makena together constitute a luxurious enclave of velvet golf courses and pristine beaches, where nonguests feel distinctly unwelcome. In theory, outsiders are free to use any of the beaches, but with magnificent Oneloa Beach lying just beyond Makena, few bother.