Wailea Guide

Wailea Guide
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Address , Wailea, HI
Wailea, best known for its beautiful beaches, luxury resorts, high-end shopping, and first rate golf courses, is for those that enjoy the finer things in life.

• General: Educational • General: History

Guide Series: Hawaii City Guides
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If the TV commercials of people relaxing beside a gorgeous pool while sipping on a tropical drink with a beautiful beach in the background looks like your dream vacation, then start checking into the resort community of Wailea.


Wailea means "waters of Lea" in Hawaiian. Legend has it that the Hawaiian goddess Lea transformed herself into an 'elepaio (a forest bird) and flew down from Haleakala to South Maui and watch over the canoe builders. In ancient times, Haleakala National Park, which slopes behind Wailea was an agricultural area where natives grew sweet potatoes.

In the 1830's King Kamehameha III enacted the The Great Mahele land redistribution which led to cattle raising on these slopes and formation of the Ulupalakua Ranch, which still exists today. During WWII, the area was used as a training ground for soldiers.

Eventually, the Wailea Development Company was formed and began developing a master planned residential resort community.

Today, Wailea is a 1500-acre luxury resort community with over 2,000 homes and condos, 6 major hotels, 3 shopping centers, and 3 world class golf courses. The resorts and homes are fronted by 1.5 miles of stunning beaches.

The spas, golf courses, restaurants, and shopping are first rate. Wailea is located on the south side of Maui, near Kihei Guide. It's located about 30 minutes south of Kahului Airport (OGG) on off Pi'ilani Highway (Highway 31).


The Shops At Wailea is Maui's most high end shopping mall. It serves as the town center for Wailea and is located at the intersection of Alanui Drive and Wailea Ike Drive. The Shops at Wailea include upscale art galleries, high end clothing and jewelry stores, boutiques, and fine restaurants.

The Wailea Beach Walk is a 1.5 mile path that backs the resort beaches. It makes for a nice evening stroll.

Hit the links at one of Wailea's gorgeous – and expensive – golf clubs. There are 5 golf courses Wailea including Wailea Gold Golf Course and the Wailea Emerald Golf Course, both beautifully designed by Robert Trent Jones II.

Annual events include the Maui Film Festival and the Wailea Food and Wine Festival.


Polo Beach Park is located next to the Fairmont Kea Lani Maui - great for snorkeling, sunbathing and swimming.

Ulua Beach Park has a nice path to take a stroll or jog beside the picturesque beach with great sunset views. Ulua Beach was once the training area for WWII soldiers practicing amphibious landings.

Mokapu Beach is located next to Ulua Beach, and is good for diving and snorkeling activities.

Keawakapu Beach in South Kihei, and the Wailea Beach Park are best for lounging on beach chairs, snorkeling, and exploring the reef offshore.

South of Wailea are the beaches of Makena. Makena Beach State Park is located 1 mile south of the Makena Beach & Golf Resort (Formerly Maui Prince Hotel). It's a large, long, and beautiful beach, ideal for swimming, relaxing, and a getting away from the crowds at the Wailea resorts.

Makena's most impressive beaches are Big Beach (Oneloa/Makena Beach) at Makena State Park and Little Beach (Pu'u Ola'i Nude Beach) just north of it. Big Beach is a huge wide beach with white sand and fun waves. There is plenty of parking, with restrooms, picnic tables, and showers. Wear your slippers because the sand is wicked hot and it's a long trek to the shoreline. Little Beach (Pu'u Ola'i Nude Beach) is located north of Big Beach (Oneloa/Makena Beach) at Makena State Park over a small hill that separates the two beaches. Nudist (and voyeurs) come here to "hang out".


There are six luxury resorts (4 or 5 star) in the Wailea area. They are the Fairmont Kea Lani Maui, Makena Beach & Golf Resort (Formerly Maui Prince Hotel), Grand Wailea A Waldorf Astoria Resort, Four Seasons Resort Maui at Wailea, Wailea Beach Marriott Resort & Spa and the Andaz Maui At Wailea. These resorts represent the best of Hawaii's resorts. All are beautiful with easy access to the beaches that front them.

One of the most popular resorts in Hawaii is the Grand Wailea A Waldorf Astoria Resort, which stretches across 40-acre of tropical gardens, with beautiful pools, beach bars, and cultural exhibits. The Grand Wailea is a super resort (think MGM Grande in Las Vegas) with extensive amenities and activities. Even if you don't stay here, it's worth a visit to check it out. The pool area here is one of the best in all of Hawaii.

There are many luxury private condos that front the ocean but the more affordable ones are on the other side of Alunui Drive. The trade off for easy access and ocean view accommodations are the thousands of dollars you'll save on hotel rooms and restaurants. That is, if you go to Costco and pick up some food to prepare at home.