Wailea, Maui

Known for its five beautiful, crescent-shaped beaches and stellar golf courses, Wailea is a luxurious resort community in South Maui that spans 1,500 acres of land with staggering ocean views. The area exudes a sense of privacy, serenity, and freedom spread across an area three times the size of Waikiki.

 

Wailea was originally a fishing settlement and its name translates to “water of Lea” the goddess of canoe-builders. Legend has it she transformed the area into a beautiful forest for birds and would frequently fly above it to appreciate its beauty.

 

While there are five hotels tucked into the town, including the Grand Wailea Resort Hotel & Spa and the Four Seasons Resort Maui at Wailea, this community also includes distinctive condominiums and stately private homes. The area’s signature beaches include Wailea Beach, named “America’s Best Beach” in 1999, Polo Beach, with its excellent swimming and snorkeling, and Ulua Beach Park, where early morning and sunset walkers and joggers abound. The Wailea Blue, Wailea Gold, and Wailea Emerald courses make up the 54 holes of championship golf that have made Wailea so famous.

 

• The incredibly stunning landscape and ocean views 
• Upscale, high-end real estate options near world-class dining 
• An ocean lover’s paradise  

In this high-end section of Maui, Wailea residents are often successful and well-cultured. There’s a healthy mix of retirees, young families, and people who own a second home here. Many people are active surfers, runners, bikers, or swimmers who love shopping, eating out, and golfing.

 

While everywhere on Maui is more laid-back in comparison to mainland USA, Wailea does have lively energy to it, mostly due to the high number of tourists and summer visitors.

 

Anyone in Wailea will first send you to Monkeypod Kitchen, the infamous farm-to-table local eatery with fantastic Mai-Tais. Tommy Bahama is another local favorite that serves up some of the best coconut shrimp you’ve ever had. Koiso Sushi Bar in Kihei has great fresh rolls and a casual vibe, while Morimoto in Wailea should be saved for a special occasion or romantic night out. Ka’ana Kitchen at the Andaz serves up family-style fare in a lush and gorgeous setting — it’s a great spot for a big group!

 

Pint & Cork has great wine and beer lists for a cocktail, and KAPA Bar & Grill is a casual place to grab sunset cocktails with friends.

 

There is no shortage of great shopping in town, and The Shops at Wailea will satisfy any shopaholic’s fantasy with stores like Gucci, Louis Vuitton, Tiffany & Co, and Lululemon. Wailea Village shops have more casual brands like Billabong and Rip Curl.

 

Beaches and oceanfront activities are the top of every to-do list in Maui, and Wailea is no different. From the world-famous surf spot Wailea Beach to Keawakapu, the pristine waters and soft sands will take your breath away. Your life in Maui isn’t complete until you try your hand at surfing, windsurfing, snorkeling, stand-up paddleboarding, or kayaking. Wailea hosts many beachfront luaus such as Te Au Moana at the Marriott to satisfy your Polynesian culture fix.

 

Down the coast from Wailea is Ahihi-Kinau Natural Area Reserve, which boasts a renowned snorkeling area and coastal lava field. Continue for a couple more miles and you’ll come to La Perouse Bay, where lava from Maui's last eruption flowed into the sea. The site has some nice hiking trails, including the Hoapili Trail, which winds its way along the coast through some shade and then strikes inland over the lava fields to Kanaio Beach 2-2.5 miles away. 

Wailea is also home to events such as the Maui Film Festival and February’s Whale Week, as well as world-renowned spas like Mohalu at Grand Wailea. World-class golfing at Wailea Golf Club impresses golfers of all skill levels, though the gorgeous setting is sure to be a distraction during your round.

 

Wailea has elementary, middle, and high schools for children in the area as well as a mix of public and private schools. Kihei Elementary, Baldwin High School and Maui High School are the closest public school options for the area, while Seabury Hall, Montessori of Maui, and Haleakala Waldorf School round out the top private school choices.