Originally a fishing settlement, the name Wailea translates to “water of lea,” the goddess of canoe-builders. The legend runs that she transformed the area into a beautiful forest for birds and would fly above it often to appreciate its beauty. Before becoming part of the United States, residents of Wailea would live more inland, towards the mountains, where they would grow sweet potatoes (uala), occasionally venturing down to the shore to fish. After the Great Māhele, cattle raising became the dominant practice in Wailea and the land used for that purpose would eventually become the Ulupalakua Ranch.
Wailea has five beautiful, crescent-shaped beaches and spectacular golf courses. It is a luxurious resort community in South Maui spanning 1,500 acres of land with breathtaking ocean views. The area exudes privacy, serenity and freedom all in an area three times larger than Waikiki.
Five hotels are nestled into the enclave, including five-star resorts like the Grand Wailea Resort Hotel & Spa and the Four Seasons Resort Maui at Wailea. The community has an abundance of gated premium luxury condominiums, homes and estates.
Twin world-famous beaches are located here. Wailea Beach, named “America’s Best Beach” in 1999, being one and Polo Beach being the other, with excellent swimming and snorkeling. There is also Ulua Beach Park, where early morning and evening walkers and joggers abound. The Wailea Blue, Wailea Gold and Wailea Emerald golf courses make up the 54 holes of championship golf that have made Wailea a world-class golfing destination.
If you are an outing enthusiast, you do not need to venture far to find activities and excitement. Drive six miles South, down the coast, and you’ll find Ahihi-Kinau Natural Area Reserve. This reserve offers a famous snorkeling area and coastal lava field. You can continue down the same road for a couple more miles and you’ll arrive at La Perouse Bay, where lava from Maui’s last weeks-long eruption flowed into the sea. Located here are also some fine hiking trails, including the Hoapili Trail, which winds its way along the coast and then strikes inland over the lava fields to Kanaio Beach a few miles away.
Back in town, The Shops at Wailea is a destination in itself, featuring world-class restaurants and boutiques, along with premium entertainment programs. Wailea is also home to festivals such as the Maui Film Festival and February’s Whale Week. A wide variety of restaurants serve the best of everything from French to Sushi to Regional Hawaiian Cuisine. Combine all this with a treatment at one of the many fine spas, and you have the life of Fifth Avenue, in paradise!