Palau‘ea and Paeahu may have been named for the reddish ‘uala (sweet potato), which was cultivated in the uplands and was an integral part of the local diet. Fishing was also of primary importance, and the waters around Honua‘ula provided exceptional yield.

South Maui contains reminders of its former inhabitants, including shelters, mounds, platforms, and terraces, with even a surviving heiau to the south. Located on private property in nearby Mākena, Kalani Heiau is carefully preserved by the landowners and is accessible by application for cultural needs.

Of primary significance to Native Hawaiian culture is the wa‘a, or canoe, which connected voyagers across the ocean, island-to-island, and cove-to-cove. According to preeminent Hawaiian scholar Kepā Maly, early settlers used Honua’ula as a “resting place for chiefly passage” between Maui and Hawai‘i Island.

Wailea has always been a haven for the wa‘a. Today, canoe clubs carry on the legacy every time they carry their boats down the sand and onto the water—paddling out for practice, races, sightseeing, and increasingly for education, as a way to initiate visitors into the cultural significance of the wa‘a and ocean voyaging.

The peace of the exquisite Wailea area today belies the turmoil of the late 18th century, when battling Hawaiian chiefs fought for supremacy and British Captain James Cook’s arrival forever changed the way of life in the islands.

Later decades saw the advent of Western trade, the influx of disease and the sobering effects of missionary zeal on the native population. By the late-1800s, the Hawaiian village lifestyle had diminished in prominence, as a new era of ranching swept into the islands. ‘Ulupalakua and the slopes of Haleakalā became the working pastures of the pāniolo, or Hawaiian cowboys. In turn, the South Maui shoreline became an ideal ramp for these proficient riders to drive their cattle down the mountain and out into the surf, where waiting barges shipped the cattle to market.

The tradition of cattle ranching continues to this day, preserving the open spaces of Maui’s Upcountry. Haleakalā Ranch, Kaono’ulu Ranch and ‘Ulupalakua Ranch, three of Mauiʻs largest ranches, much of it spread across the slopes of Wailea, provide a soothing vista to the upward eye.

When World War II descended in the 1940s, the beaches of Wailea were designated as training grounds. Beautiful ‘Ulua Beach was nicknamed “Little Tarawa” and used by the Marines in training for amphibious landings.

In 1959, Matson Navigation bought 1,500 acres of former ‘Ulupalakua Ranch land in coastal Honua‘ula to build a resort complex, but no development began at that time. The 1960s census showed that only about 1,000 people lived in South Maui, from Mā‘alaea to Mākena.

Alexander & Baldwin took over ownership in 1969, and in 1971, A&B partnered with Northwest Mutual Life Insurance Company to form the Wailea Development Company and build a residential resort community.

As sugar and pineapple production started to decline on Maui, the concept of an “integrated residential resort community” gave developers greater flexibility in planning and gave future owners a range of housing diversity, according to the Wailea Resort Association. Commercial properties and recreation, such as golf and tennis, were included in the planning. Construction began in Wailea in 1972 and a pipeline was built in 1979 to bring water from ‘Iao Valley to South Maui. In 1987, the Wailea Community Association was developed “to maintain the resort in a first-class style through management of common property maintenance and design controls.”

Today, Wailea Resort ambles along one-and-a-half miles of spectacular shoreline, with a paved public walkway following the oceanfront bluffs. The resort comprises more than 2,000 homes and condominiums, six major resort hotels and spas, three shopping centers, countless fine restaurants, three renowned golf courses and a tennis center. Five crescent-shaped beaches provide opportunity for swimming, snorkeling, scuba diving, stand-up paddleboarding and whale watching. And several of the resorts offer the authentic Hawaiian experience of paddling a wa‘a down the coast of Wailea, the graceful “waters of lea.”