Over the past 30 years, the South Maui town of Wailea has developed into an exceptional community of world-class resorts. Yet, unlike other commercial development, it still retains a charm and a sense of privacy not often found in popular resort towns.
Maybe the name has something to do with it. According to one translation from the ancient Hawaiian language, Wailea means “Waters of Sacred Happiness.” While not all activities here involve water, they all bring a different type of happiness to visitors to this part of the Valley Isle.
We tend to stay in Wailea when in Maui because, well, we’re Four Seasons people and like the slower pace. So, whether you’re coming for the day or basing an entire Maui vacation here, you can enjoy these fun Wailea activities.
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1. Visit Wailea Beach
You can’t go to Wailea without spending time on its famous beach. Located in front of Four Seasons Maui and Grand Wailea Resort, Wailea Beach has vast stretches of soft sandy beach and crystal-blue waters between two lush green rocky points.
The beach offers a beautiful south Maui vista of Lanai, Kaho’olawe, and Molokini too. You can spend a relaxing day sunbathing or swimming in the calm waters. Snorkeling can be excellent here in the early morning when you can see a variety of marine life. You’ll also find a lot of kid-friendly activities, including body surfing and boogie boarding.
Wailea Beach is a great place to take a stroll as the Wailea Coastal Walkway is a 1.5 path between Ulua Beach and Polo Beach that is both wheelchair- and stroller-friendly. It’s a great place to take in Hawaiian wildflowers and the wonderful smell of hibiscus trees. At night, tiki torches line the path, adding to the ambiance.
2. Grab a Tee Time at Wailea Golf Club
Golfing is Hawaii’s top luxury activity, which is no wonder when you have a world-class golf resort like the Wailea Golf Club in South Maui. The club has instruction for golfers of all levels at the David Leadbetter Golf Academy, plus a wide array of services and amenities.
Wailea Golf Club is perfect for a myriad of golf instruction at all levels. Golf enthusiasts will find three top-rated links here.
Wailea Gold is considered one of the 100 best courses in the United States. Wailea Blue has stellar ocean vistas, while Wailea Emerald is a favorite of many female golfers. Each with varying levels of difficulty and gorgeous views of the ocean horizon. Playing a round at the club is one of the best things to do in Wailea, Maui.
3. Feast at a Wailea Luau
At Grand Wailea awaits one of Maui’s most famous attractions, the Grand Luau at Honua`ula. Featuring Hawaiian storytelling and Polynesian dancing, this luau is definitely one of the best things to do in Wailea. The focus on storytelling is what sets the Grand Wailea luau apart from the others, as you’ll hear tales about mermaids, voyagers, ancient Hawaiian gods and goddesses, and more.
The show features a mix of traditional swing hula as well as free-form dance. Learn about the voyages of La’amaikahiki and Moikeha, the Polynesians who first traveled to Maui, along with tales about Pele, the volcano goddess, Lilinoe, the goddess of the mist, and the Mermaid of Maui.
Not only are the stories exceptional here, so is the food. Sample papaya salad, roasted macadamia mahi-mahi, kalua pig, pineapple upside-down cake, guava mousse, allergy-friendly dishes, and vegetarian/vegan options. The evening finishes with a fire-knife dance and a torch lighting ceremony to make for one of the more memorable Wailea activities.
We have also enjoyed Te Au Moana luau at Wailea Beach Marriott. Te Au Moana is translated to ” the ocean tide,” which is significant because tides connect islands and people — a theme woven into the luau performances set against the ocean as a backdrop.
4. Stay, Dine & Spa at Four Seasons Maui
Maui’s south shore is known for its outstanding cuisine, so you won’t want to miss the restaurants at Four Seasons Resort. I can vouch for all of them.
Guests of this resort community will have the luxury of being able to sample all of the offerings here easily. Still, even if you don’t stay at the Four Seasons Maui, you’ll want to return because of the breadth and quality of food at this Wailea Beach resort. Choose from three restaurants, starting with Wolfgang Puck’s Spago set on a lanai under the stars. The cuisine is a mixture of Californian and Hawaiian with locally sourced ingredients, plus specialty cocktails.
For Italian fare, choose the Zagat-rated Ferraro’s, with its authentic Cucina Rustica located on a bluff overlooking Wailea Beach. Ferraro’s is considered one of the most romantic spots to eat dinner in Hawaii, so it’s perfect for date night. Diners enjoy live music in the evening from Tuesday through Friday.
For a more casual experience, DUO offers various nightly themes, including an all-you-can-eat Raw Bar with oysters, ceviche, poke, crab, and shrimp. For carnivores, Market Night offers a Hawaiian version of churrascaria. A sommelier serves all three Four Seasons Maui restaurants to guide you in finding the perfect bottle to pair with your food.
Book Four Seasons Maui with Four Seasons Preferred Partner BenefitsThrough me, you have access to extea perks like daily breakfast for two, a $100 resort credit and more at no extra cost to you. Read my full review and send me your dates.
5. Visit Makena Beach State Park
One of the most photogenic beaches on Maui is located in Makena Beach State Park. Divided into two sides, Big Beach and Little Beach, it’s also one of the largest and widest beaches in the state.
Makena Beach is hidden by Kiawe forests and mango groves and still retains somewhat of a primitive feel compared to other parts of the island. Big Beach, also known as Oneloa Beach, is ideal for swimming, bodyboarding, skimboarding, and snorkeling.
Always pay attention to ocean conditions when here as the water is, smooth one moment and produces a rogue wave the next. Check out the little cove at the southern end if you come here with kids.
You need to take a brief hike to get to Little Beach, accessible from the north end far of Big Beach. Wear sturdy shoes as you’ll have to climb over lava formations and Pu`u Ola`i, a cinder cone created from a Haleakalā eruption, to get there. This secret beach has calmer conditions and sunny and shady spots. Note that lifeguards are not located here and that the hidden area is an unofficial nude beach, although everyone is welcome.
6. See the La Perouse Dolphins
Start your day early if you want to see the elusively beautiful Spinner Dolphins in La Perouse Bay. Located about 17 minutes south of Wailea at the end of Makena Alanui Road, La Perouse Bay is a destination in itself as it’s the site of Maui’s most recent volcanic activity in 1600.
Early morning is the best time to see the dolphins splashing, playing, jumping, and simply having a good time. Known as Keone’o’io in ancient Hawaiian, La Perouse Bay is on one end of Maui’s historic King’s Trail, another of the best Wailea attractions on this list (below).
Just north is the Ahiki-Kinau Natural Area Reserve, a popular snorkeling and scuba diving spot. Visitors will see many endangered sea life, marine mammals, tropical fish, and Hawaiian green sea turtles.
7. Hike the King’s Trail
After your early morning at La Perouse Bay, go back in time on the King’s Trail. King Pi’ilani of Maui commissioned the path made of lava rocks in the 16th century as part of his plan to unify the island chiefdoms.
The path is also known as Hoapili Trail. The path is a great place to see what ancient Hawaii looked like. This hike is unlike any other as it’s full of lava rock formations, coral, and wild goats. Don’t veer off the path as the area is a legally protected historical site.
The trail is over 10 miles long and isn’t easy, so many people turn around at Kanaio Beach. If you love history, this hike will be one of your favorite things to do in Wailea with its ancient sites, including the Hawaiian village Keone’ō’io.
Make sure you have sunscreen, a hat, and plenty of water.
8. Go on a Kayak Tour
With so many gorgeous beaches and the ocean always nearby, going on a kayak tour is one of the best ways to explore the gorgeous southwest coast. This popular Wailea activity is ideal for couples and families.
Several companies offer kayak adventures with certified marine naturalists, leaving from Makena Landing. Choose from expeditions that include traveling to Makena’s Turtle Town to explore gorgeous reefs and hopefully spy the green sea turtles who live here.
Other tours will explore various coves or include dolphin or whale watching when in season. This eye-opening experience will leave you wanting more. Some companies even give you digital photos to remember your experience.
9. Go Snorkeling — On Your Own or With a Sea Scooter
The ocean near Wailea, including Molokini, is a world-renowned snorkeling area, yet if your snorkeling skills aren’t that good or you want to see more, take a Sea Scooter Snorkeling Tour.
After learning basic safety information on the scooter, you’ll head out on these devices that travel up to three miles an hour through the water. Scooter snorkeling gives participants a chance to view more marine life like sea turtles than you’d normally see on snorkeling tours as you cover more ground. All gear is provided.
If you would like to take an organized snorkeling tour to Molokini on a catamaran, these leave from Makena beach in front of the resort.
10. Feed Your Soul at Wailea Healing Center
Take time out of your schedule to visit the Wailea Healing Center. You’ll find services to treat your body and mind, including acupuncture, intuitive life coaching, cupping therapy, professional wellness training, and classes like mantra singing and breathwork ceremonies.
The center’s outdoor massage services are among its most popular offerings. They include types like decompressing Maui massage, reflexology, Lomi Lomi, Swedish, cranial-sacral therapy, and golf rehabilitation massage, a perfect complement after a day on Maui’s golf courses.
You can even schedule a Wailea Healing Center session at your Wailea Beach resort or vacation rental.
11. Browse the Shops at Wailea
Suppose you feel the need for retail therapy, head over to the Shops at Wailea. Conveniently located near most Wailea resorts, the high-end shopping destination houses boutiques from internationally renowned designers like Gucci, Louis Vuitton, Bottega Veneta, St. John, Coach, and Barron & Leeds, along with surf shops, casual cafes, and fine dining. If you want to find a unique purchase to remember your vacation in south Maui, this is the place to go.
Tip: Four Seasons runs a shuttle within Wailea, including to the Shops at Wailea
12. Play a Set at Wailea Tennis Club
If you love tennis or want to get some exercise and play a few sets, head over to Wailea Tennis Club, considered one of the best United States Tennis Association clubs in South Maui.
Players will enjoy the best tennis clubs instructors on the island, newly remodeled facilities, first-class services and amenities, and impeccable grounds. You’ll enjoy spectacular weather and incredible views at Wailea Tennis Club as you perfect your tennis game or even play a game of pickleball.
13. Enjoy the Sand or a Sunset at Keawakapu Beach
Maui sunsets are irreplaceable, and while you have a choice of your favorite location to view the sun sinking into the Pacific, not all sunsets are created equal.
Keawakapu Beach is one of the best places to watch a sunset on Maui’s south shore. Find out the exact time of the sunset and go early to make a romantic evening.
Keawakapu Beach is also a top spot for scuba diving and viewing Hawaiian green sea turtles.
14. Stay at Fairmont Kea Lani Hotel on Polo Beach
Located between the Fairmont Kea Lani Hotel and the Polo Beach Club, Polo Beach boasts a pair of sandy golden crescents perfect for a romantic walk when staying at the Fairmont Kea Lani, one of the best Wailea resorts in South Maui.
Polo Beach has a great snorkeling spot around the rocky point on the beach’s north end.
Book Fairmont Kea Lani with benefitsThis resort is second to Four Seasons as my most requested property on Maui. Through me, you have access to Virtuoso amenities that include daily breakfast for two, a $100 resort credit and more. You can actually book online*.
*The desktop version of Virtuoso.com is where you’ll search rates and book online. To enable the desktop version from a mobile device, after clicking on a Virtuoso hotel link, scroll down to the navy blue section at the bottom of the web page and click “Full Site.” When searching rates, do not input children ages 17 and under as they will be priced as adults. I’m notified when you book and will add them when I contact you about your reservation. You can also use my form to request rates.
15. See Hawaiian Green Sea Turtles at Turtle Town
You might get lucky and see Hawaiian green sea turtles as you go about your day in the lovely ocean water. However, Turtle Town between Makena’s One’uli Black Sand Beach and Nahuna Point is famous for them.
You can stand-up paddleboard, kayak, or snorkel here on your own or with an organized tour. One of the highlights is that turtles aren’t too afraid of people.
(During one of our last visits to Wailea, our snorkeling tour had to skip Turtle Town because the ocean was too choppy.)
16. Learn History at Keawalai’s Congregational Church
One of the more interesting Wailea attractions is experiencing history at this landmark church. Established in 1832, the first structure was built of pili grass and then reconstructed later using lava, timber, and coral mortar.
Located just south of Makena Landing, the church is open to the public for services in Hawaiian with hula and chants.
17. Eat at Monkeypod Kithen by Merriman
For families with kids, Monkeypod Kitchen by renowned local chef Peter Merriman is a great place to eat. While kids chow down on pizza, parents can enjoy appetizers and drink specials, including handcrafted cocktails and 36 microbrews.
They pour a stellar Mai Tai — the Monkeypod Mai Ta. Ingredients are sourced via partnerships with local growers, brewers, farms, and artisans. It’s one of the most fun things to do in Wailea, Maui, as you can try Kalua pork pizza, fish tacos, burgers, and poke but feel good about what you’re eating.
(I’ve also eaten at Monkeypod in Ko’Olina on Oahu, and it’s just as delicious.)
18. Order Shave Ice at Surfing Monkey
The odds are that your Wailea Resort has shave ice, but you can eat like a local and grab some at Surfing Monkey at Shops at Wailea. Popular flavors include pina colada, banana, and wild cherry, but they also have vegan and organic ice cream too.
19. Go Horseback Riding
Are you looking for something different from the usual South Maui experience? Rub elbows with the paniolos, the Hawaiian cowboys at Makena Stables.
Try a morning or sunset horseback ride to see a beautiful island panorama. Tours are small and perfect for families with kids ages 13 and older.
20. Dinner and a Show at Mulligans
If you’re up for live music and want a change from the typical Hawaiian entertainment, try Mulligans on the Blue. Located near Fairmont Kea Lani, Mulligans is the only Irish pub in Maui.
The nightly entertainment here makes this venue one of the most fun things to do in Wailea, Maui for nightlife seekers. Weeknight entertainment includes Mulligans Magic Show, Uncle Willie K, the Makai Jazz Group, and Friday nights with Soul Kitchen. Saturdays have a rotating lineup while Sundays feature the Celtic Tigers. Check their calendar before you go.