8 Reasons Why You Should Stay In Wailea
On the south side of Maui, you’ll find the luxurious region of Wailea. This area of Maui is sprinkled with high-end resorts and condos surrounded by world-class golf courses, fine dining restaurants, and exquisite white sand beaches. Whether you plan to stay in the heart of Wailea (or adjacent Makena), or just 10 minutes down the road in Kihei, there are many reasons to be in Wailea during your vacation on Maui. (Wailea is pronounced why-LAY-uh. Here’s a map of Maui’s regions to help orient you to its location.)
8 Reasons Why You Should Stay in Wailea
Visit The Shops at Wailea
The Shops at Wailea is smack dab in the middle of the gorgeous resorts of Wailea. This venue is open 10am-9pm everyday and features 70 retail luxury and lifestyle stores, including world-renowned brands and top island restaurants. This is an open-air shopping area full of luxury brands, as well was wonderful locally-made souvenirs for loved ones. There are outstanding full-service restaurants to choose from, including two of my favorites — Tommy Bahama and The Pint & Cork, as well as grab-and-go stores like Island Gourmet Markets and Lappert’s Hawaii Ice Cream & Coffee. Anyone can participate in the educational cultural activities like ukelele lessons and lei making, and enjoy the free Polynesian dance show on Tuesdays and Thursdays at 5:30pm. (Check their events page for the latest schedule when planning your trip.)
Dive into the Upscale Dining Scene
There are plenty of approachable dining options in Wailea, but the highlight of Wailea’s dining scene is the world-renowned restaurants associated with celebrity chefs. Award-winning culinary talent creates the perfect experience for guests with exquisite ambience, outstanding service, and top-notch dishes. You’ll find a variety of dining options at each of the Wailea resorts, as well as more restaurants at nearby shopping areas like Wailea Gateway, Wailea Village, and The Shops at Wailea.
My favorites include Morimoto Maui at Andaz Maui, Monkeypod Kitchen in the Wailea Gateway, and Humuhumunukunukuapua’a at Grand Wailea (named after the Hawaii state fish). I also recently enjoyed an unforgettable meal at The Restaurant at Hotel Wailea — ranked in the Top 10 Best Restaurants in Hawaii by Open Table’s Diners’ Choice Awards. In a garden bungalow setting with bohemian-style canvas and wood decor and lush green surroundings, the Prix Fixe menu delighted our tastebuds the whole way through. If you’re looking for an exceptional, unique experience, I recommend trying The Restaurant for your next dinner splurge! Read our Top 20 Favorite Restaurants blog with more recommendations!
Test Your Golf Swing at World-Renowned Golf Courses
Located slightly higher up the hill from the sea-level beachfront resorts are three amazing golf courses offering unbelievable views of the ocean and coastline. The Gold, Emerald, and Blue golf courses, two full-service pro shops, and Wailea Golf Academy have collectively earned over 170 honors for aspects like course design, customer service, and pro shop excellence. The Gold course has consistently been ranked in the top 100 resort courses to play in the United States and has been honored in publications like Golfweek, Golf Digest, Golf Advisor, and Golf Magazine. Stay close by at Ho’olei Wailea Beach.
Experience a Nearby Luau
You cannot come to Hawaii and not experience a luau! This all-in-one experience offers signature Hawaiian cuisine dishes such as poi, kalua pig, laulau, and haupia, traditional ceremonies and music, and various forms of Polynesian dance including Hawaiian hula. The best place to see a luau in South Maui is in Wailea where many of the Wailea resorts offer outstanding luau options. My personal favorites include the Te Au Moana Luau at Wailea Beach Marriott Resort and the ʻAhaʻaina Luau at Grand Wailea.
Hike Along the Lava Rock Trail of Hoapili
Just south of Wailea, continue down past Makena Beach and you’ll reach La Perouse Bay, which begins the Hoapili Trail — originally the King’s Trail. Hoapili Trail is technically 10 miles long, but is typically only followed to the Hanomanioa Lighthouse for a round trip of 3 miles in-and-out. This trail is unlike any others on the island! Begin with gorgeous views of La Perouse Bay with white and black sand mingling together, walk along the forest area full of goats playing and feeding, then the last half of the trail to the lighthouse traverses the lava rock terrain created by the last eruption on Maui in 1790! Insider tip: closed-toed shoes are essential as that lava rock can slice up your toes if hit wrong. Also, the sun bakes the lava rock, so you will want to get there before the sun gets too hot for the trail to be enjoyable. Find out our Top 5 Hikes on Maui here.
Loosen Up at A World-Class Spa
While just relaxing on the beach can instantly loosen your muscles and allow you to breathe a little easier, why not encourage a deeper level of relaxation with an all-day spa experience at some of the leading resort spas in the nation? Rejuvenate, relax, and unwind either in the privacy of your own massage room, beachside at a private cabana, or with an all-day relaxation experience meandering between treatments, plunge pools, and steam rooms. Wailea is home to some of the top-ranked spas in America, including The Spa at The Four Seasons Resort at Wailea, Willow Stream Spa at Fairmont Kea Lani, and (pictured) Grand Wailea Resort’s Spa Grande (currently limited and under renovation). (Photo courtesy of Grand Wailea Resort.)

Relax on the Gentle White Sand Beaches
The stretch of beaches fronting Wailea feature crystal clear waters and soft white and tan sand, set against a backdrop of perfectly landscaped resorts. Wailea beaches include Mokapu, ‘Ulua, Wailea, and Polo, all offering nice snorkeling spots and a place to relax and enjoy great views of Molokini Crater and the islands of Lana’i and Kaho’olawe. Get picked up from Maluaka Beach for a snorkel tour, whale watch, or sunset sail with Kai Kanani, Wailea and Makena’s exclusive catamaran charter.
One of my top favorite beaches on Maui is just south of Polo Beach, approximately a 5- minute drive to Makena Beach (aka “Big Beach”). This is one of the longest stretches of soft white sand beaches on Maui, but tends to have a dangerous shoreline break so I don’t encourage this beach for swimming or snorkeling. Watching the locals spin around on skimboards and boogie boards doing flips in the air is something to behold! Take note of important ocean safety tips in our blog on Maui Beach Tips.
Stroll the Wailea Beach Path
If your wallet is hurting and you’re looking for a lovely activity free of charge, take to the Wailea Beach Path! Plan to stop for pupus (appetizers) or mai tais along the way at the oceanfront resort dining options, or have a romantic sunset walk with your significant other. This paved pathway meanders 3.5 miles starting from Ulua Beach to the north and ends at Polo Beach to the south. This is a great option for families or couples to enjoy some whale watching from the shore or experience a few different beach settings in gorgeous Wailea.
Watch our Facebook Live as we walk from the South end to the North end of the Wailea Beach Path:
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