For an island smack-dab in the center of the Pacific Ocean, Maui is home to an astonishing array of landscapes.
From the vertiginous cliffs of the West Maui Mountains to the ghostly terrain of Kaupo, each place is sublimely beautiful and wonderfully distinct. It’s no wonder Mark Twain came to Maui for a week and stayed for five: There are countless places to experience and see.
But if there’s one spot that shouldn’t be missed, it’s the Valley Isle’s gorgeous south shore.
Consider it the quintessential paradise often rendered in postcards: Sugary sand, crystalline waters, tony resorts, glossy golf courses—and just enough of a divey aloha vibe to make you feel like you’re on a South Pacific Spring Break.
Whether you’re in Kihei for a week or just passing through Wailea for a day, here’s how to make the most of your South Maui stay:
Say Hello, Sunshine
Few sights are more spectacular than a South Maui sunrise, where the rosy glow of the sun ascending over Haleakala is greeted by a bevy of sassy native birds.
And what better way to relish the splendor than aboard a 65’ catamaran? The Kai Kanani offers early-morning adventurers a taste of the island’s daybreak beauty on its Molokini Express—a two-hour excursion to the county’s snorkeling mecca off of Maui’s southwestern shore.
Feel like staying (mostly) on land? Grab some snorkel gear and shoot south to Ahihi Kinau Natural Reserve. Teeming with iridescent fish, this clear-water cove on Makena’s rugged coast offers some of the most exquisite snorkeling on the island.
Feel like staying (mostly) on land? Grab some snorkel gear and shoot south to Ahihi Kinau Natural Reserve. Teeming with iridescent fish, this clear-water cove on Makena’s rugged coast offers some of the most exquisite snorkeling on the island.
Turn Back Time
Post-ocean fun, take advantage of Makena’s many wonders by sneaking in a touch of Hawaiian history.
Built in 1832, Keawala’i Congregational Church boasts tranquil grounds and a past rich enough for the books. Slip into the stone church and step back centuries, when Makena was little more than acres of gorgeous beach and parched kiawe wh pigs were offered as tithes. Just be sure to follow local custom by leaving your slippahs at the door.
Get Grindz
Skirt the crowds at Kihei’s cafés and head to Hawaiian Moons for a picnic lunch instead.
With both a hot bar and a salad bar, this south side staple offers everything from Sweet Thai Coconut Chicken to fresh-baked banana bread. Oceanfront tables across the street at Kamaole Beach give you an up-close look of toothpaste-blue water and, during whale season, a show-offy Humpback or two.
In the mood to be wined and dined? Pardon the parking lot view at Matteo’s Osteria for their scrumptious Italian eats and swoon-worthy list of vinos.
Hang Ten
No trip to the south or west side is complete without an afternoon surf sesh.
Cove Park is often packed for a reason: With its lulling waves and breathtaking backdrop, it’s the perfect place to learn how to longboard. Book a private lesson with Maui Surf Lessons, where you’ll be guided through basic instructions and surf etiquette to get you standing in half the time it’ll take you to say Hawaii’s state fish.
Simmer Down
Soothe your sore muscles with a massage at Maui’s Best Massage, where tailor-made treatments and convenient location at the Island Surf building in south Kihei, turn a standard spa session into a truly transcendent experience.
To this day, Sam and his team have given us the best massages of our lives. Period. Their pricing is good (especially relative to all the resorts nearby), and you can get many different treatments. Call (808) 426-7418 or go to them at 1993 South Kihei Road Suite 19.
Sip Some Bliss
Sustain the serenity you found at the spa by peacing out with a signature cocktail or locally-crafted beer at Bev Gannon’s eponymous eatery.
Tucked into the verdant hills of Wailea, its unobstructed views of Maui County’s outer islands will leave you slack-jawed and stirred.
Be Bedazzled
It’s not just a myth: Maui sunsets are undeniably divine.
Rather than sharing the spectacle with the hordes of onlookers on the grass at Kam III, take a jaunt to Naupaka Beach. Known as “Black Sands,” this otherworldly strip of onyx beach requires some effort to find, but its secluded location and dramatic scenery are well-worth the trip. Try not to blink as the sun dips below the horizon: A fortunate few might catch the legendary but often-elusive green flash.
Take a Hike
Stroll down the steps at the Marriott to the Wailea Coastal Walk, a 1.5 mile path that hugs the coastline and takes you past the glitzy resorts that secured Wailea as a worldwide destination.
With unseen waves crashing ashore and pockets of pure silence, it’s a prime spot to savor the lusty Maui moonlight and starry night sky. Bonus points: Time it right, and you might catch the tail end of one of the hotel’s nightly luaus as you amble by. Also, don’t be afraid to drive down further south where the road ends to see some raw, fresh-island hiking.
Stir it Up
Sailing high on a second wind?
Hit up Monkeypod for an island libation and a chance to chat with locals celebrating pau hana, then head to Ambrosia (AKA VIBE Maui)—a lively martini lounge that serves a good pour and features an oft-packed dance floor. If darts and dusty juke boxes are more your thing, step on over to the Dog & Duck, an Irish watering hole famous for its blonde bartenders, Trivia Thursdays, and rowdy, late-night crowd.
Looking for something more sedate to wind down your day? The lobby bar at the Four Seasons blends posh digs with sophisticated Hawaiian style, offering live music, Maui-inspired mélanges, and open-air views of the moonlit water, proving there’s no better way to say aloha ‘oe to your day. Or, rather, a hui hou—because after a time like this, there’s no doubt you’ll be back for another South Maui stay.
