About Wailea, Maui

Kihei’s neighbor to the south, Wailea is an area best known for its high end resorts, luxury shopping, picture-perfect stretches of golden sand beaches, scenic sunsets, top notch dining options, golf courses and award-winning spas. When celebrities come to vacation on Maui, Wailea is often their playground of choice, and we can clearly see why.

Wailea Legends

Wailea’s cultural significance often begins with the fascinating legend of Lea, the Hawaiian Goddess of Canoe Builders. She was said to have transformed into an ‘elepaio, or forest bird, and would fly over the southern shores of Maui’s beautiful coastline. The area thus became known as the ‘waters of Lea,’ or Wailea.

Wailea History

For ancient Hawaiians, Wailea acted predominantly as a fishing village, which were often traded for sweet potatoes by those living further up on the fertile slopes of Haleakala Volcano. In 1848, King Kamehameha III enacted the Great Mahele Land Redistribution Act, and cattle raising soon became the major practice in the area, all the way up to what is now Ulupalakua Ranch.

After serving as a training area for the U.S. Marines during WWII, Wailea was then deemed as a residential resort community in 1971 after the partnering of Alexander & Baldwin Company and Northwest Mutual Life Insurance Company of Milwaukee. The 1500-acre area was planned to include both commercial and recreational amenities, and was further developed to the standards of the Wailea Community Association.

Things to do in Wailea

Today, Wailea boasts a number of impressive luxury resorts, including the acclaimed Andaz Maui, Four Seasons, Grand Wailea, Fairmont Kea Lani and Hotel Wailea, as well as three world class golf courses, shopping centers, and an award-winning tennis center. When visiting this gorgeous area of Maui, we highly recommend enjoying a stunning sunset at beaches like Keawakapu, Polo, Wailea, Ulua and Mokapu, as well as dining at Monkeypod Kitchen, Capische, Ferraro’s and Humuhumunukunukuapua’a.

Treat yourself to a luxurious spa treatment at Spa Grande or Willow Stream Spa, and don’t miss some of Wailea’s best annual events, including the Maui Film Festival, Taste of Wailea, and Restaurant Week! For those more active, the ocean is usually calm and perfect for snorkeling, scuba, kayaking, canoeing, and swimming.  Both areas bordering Wailea (Makena and Kihei) offer boat trips to Molokini and beyond.