Wailea - Lots of Resorts

The name "Wailea" holds a significant and beautiful meaning that dates back to ancient Hawaiian times. It comes from the Hawaiian words for water, "wai" and sacred, “lea”, so the name Wailea can be interpreted as "Sacred water". This name reflects the area's historical roots as a fishing settlement and its connection to the goddess of canoe-builders, who, as the story goes, transformed the land into a lush forest for birds in ancient times.

During World War II, Wailea served as a training area for Marines. In 1957, Matson Navigation Company acquired land in Wailea, with Alexander & Baldwin taking full ownership in 1969. The Wailea Development Company was formed in 1971 to create a residential resort community, leading to the establishment of the 1500-acre Wailea Resort with diverse housing options, commercial properties, and recreational amenities like golf and tennis.

In more recent years, Wailea has evolved into an exquisite destination with over 2,000 homes and condominiums, six major resort hotels, commercial centers, a tennis center, and three world-class golf courses (Gold, Emerald, and Blue). The Wailea Community Association was established in 1987 to maintain the resort's high standards through property maintenance and design controls.

Moreover, Wailea is home to prominent establishments like the Grand Wailea Resort, Four Seasons Resort Maui, Fairmont Kea Lani, Marriott Wailea Beach, and various other luxury accommodations. The Grand Wailea Resort itself has a history dating back to its establishment in 1991 by Japanese developers who envisioned it as a cultural asset inspired by Maui's natural elements like water, light, sound, flowers, trees, and art. The resort's iconic Love Tree symbolizes growth and interdependence between Wailea and Maui. The area also boasts underground utilities, landscaped roadways, restaurants, championship golf courses, tennis facilities, shopping centers, and beautiful beaches.

Our Wailea South walk takes you along the beautiful Wailea Beach Path from the Fairmont Hotel, past the Four Seasons Hotel and Wailea Beach, ultimately to the Grand Wailea Resort, and back to the South again. What’s the name of that restaurant again? Oh yeah, Humuhumunukunukuāpuaʻa. Say that one three times fast.

Wine Walking Routes

Wailea - North

Wailea - South

The Minds of Todd and Tana

The Minds of
Todd and Tana