The First-Class Resort Destination of Wailea – Now & Then

Today, Wailea is a premier destination resort that rivals any resort in the Hawaiian Island chain. In terms of luxury hotel accommodations on the ocean, it boasts the newly opened Andaz Maui at Wailea, the Grand Wailea Resort, the Four Seasons Resort Wailea, the Fairmont Kehalani Resort, and the Marriot Wailea. Like other major resort areas in the islands, it also offers luxury condominiums and exquisite residential homes.


Recommended Activities

Because of its many accommodation options, the breath and diversity of activities at Wailea has matured:

Wailea’s Beginning

But how did Wailea come to be and when? While old time Maui residents consider the early 1970’s as the start of the development of Wailea, it actually began around 1955. That is about the time Matson Navigation, a subsidiary of Alexander & Baldwin, obtained an option to purchase 1,500 acres from Ulupalakua Ranch.

With the beautiful white sand beaches of Keawakapu, Mokapu, Ulua, and Wailea fronting the planned resort area, it certainly seemed a no-brainer location to compete with what was being developed on the west side of the island at Kaanapali by another longtime local company, American Factors. However, overgrown with keawe (mesquite) trees and no water source nearby, “lolo” (crazy) was used more than once by locals at the time.

Little did everyone know that the State was willing to provide seed money to create a water system for the area. While most residents on the south shore of Kihei, Wailea, and Makena know their potable water comes from the valleys of Central Maui, they might not know that it was mainly because of the developers of Wailea and Makena sharing the cost of the water system.

True to the development of many visitor related destinations however, liberties were taken to romanticize the destination. An article in the February 22, 1956 Maui News notes that Wailea means “water of pleasure,” according to one Hawaiian dictionary. An article in the May 11, 1957 described the Wailea area as “Little Tarawa.”

Luckily, all visitor publications today correctly notes Wailea means “water of Lea,” Lea being the goddess of canoe making. Unfortunately, the Pools at Oheo are still being described by the name Seven Sacred Pools, but that is another story.

Surely the visionaries of 1955 had a dream that Wailea would be something special. It didn’t hurt that it had beautiful beaches, was on the leeward side of Haleakala, which afforded it sunny weather, and it faced west for incredible sunsets. It also didn’t hurt that it was close to the main commercial airline terminal of Kahului Airport.

Wailea Today

So while the names and operators of the luxury hotels may have change and while the area called Wailea today has expanded from the original 1,500 acres, it has definitely matured into a first-class resort destination that Maui is proud of.

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