Sometimes after a long day of lounging around on Wailea beach, lounging around by Wailea pool, and lounging around at your resort bar, you still have some energy left. And while most of Maui is early to bed and up with the sun, nightlife still thrives in resort towns.
Wailea is home to some classic cocktail bars, and welcoming restaurants that stay open past sunset. If you prefer a low-key evening, we have some suggestions for that as well!
Not sure what to do with your Wailea evening? Read this guide
Cocktails at Monkeypod Kitchen
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Monkeypod Kitchen is one of the best restaurants on Maui, serving Hawaiian influenced food made from locally grown ingredients.
The atmosphere is a welcoming blend of quality dining and aloha spirit, where diners can relax as they tuck into seared ahi steak, and bulgogi pork tacos.
But the real star of the menu is the cocktail list. The Monkeypod Mai Tai is possibly the best Mai Tai on Maui, and it has some tough competition.
Come along for happy hour between 3:30pm and 5:00pm, and you might find you don’t leave until closing time.
A Romantic Dinner At The Four Seasons Ferraro’s Bar e Ristorante
Dine under the stars at Ferraro’s Bar e Ristorante in the Four Seasons Maui. Wailea’s only oceanfront restaurant, Ferraro’s is an Italian restaurant that serves up romance alongside the pasta and pizza.
Book in advance, and make sure to save room for the delectable desserts.
Reservations made for after 8:00pm can enjoy 50% off wine by the bottle.
Live Music At Mulligans on the Blue
The only Irish pub on Maui, Mulligans on the Blue has become a Maui institution—especially for fans of live music.
A typical Irish pub welcome combines with Maui aloha at Mulligans, creating a relaxing evening experience where guests are sure to feel at home.
Choose between a traditional Irish Guinness and the local Maui Brewing Company, for the perfect accompaniment to their pub food menu.
Or just grab a whiskey instead, and enjoy whoever is providing the entertainment that night.
Kick Back At Tommy Bahama
Head to the Shops at Wailea to get yourself a Tommy Bahama shirt, and then pop into the restaurant for cocktails, conversation, and celebration.
Tommy Bahama is all about that island life, and you can toast that sentiment with a glass of their island rum.
While you’re at the Shops at Wailea, check out to see if they have any live music scheduled. There are often evening performances from local artists.
See The Panoramas At Gannon’s
The first thing you notice at Gannon’s are the incredible views this lively bar has to offer. Book a spot on the lanai, and enjoy a classic Maui sunset as you tuck into Joe’s Famous Meatloaf.
Then head across to the red bar, for a buzzing atmosphere and some specialty cocktails.
Once you’ve tried their Wailea Spritz, you’ll understand there’s much more to Gannon’s than the Maui views.
Feast at Mokapu Luau
If you’re after a luau with a difference, the Feast at Mokapu is an upscale evening that combines luxury with tradition.
Found at the high-end Andaz hotel, the Feast at Mokapu is a culinary experience and a masterclass of storytelling.
It’s also a more expensive luau, so be prepared to take advantage of the handcrafted cocktails included in the ticket price.
For a slightly (and we mean slightly) cheaper option, the Grand Wailea also has a fantastic luau to check out. This interactive luau is a wonderful choice for families and couples.
Sunset Cruise
Watching the seas turn golden with the sunset is one of the many highlights of a sunset cruise, which can be found in the waves at Wailea.
Drinks, food, and often live music accompany a lazy sail across the waters of Maui, where you can watch the spectacular sunset silhouetting Molokini island.
This is the perfect romantic experience for couples looking to celebrate, but anyone will fall in love with the shimmering waves of a sunset cruise. Make sure to take your camera!
Go Star-Gazing
Book a tour, or make your own way to Makena, where the clear skies grant you serene views of twinkling stars. A relaxing way to end a busy day in Wailea, star-gazing on Maui fills you with a sense of calm.
Take a telescope if you have one, or simply enjoy sitting back and watching the heavens move above you.
Take A Sunset Selfie
The sunsets on Maui are world-famous, and you have to stop and watch at least one. Although the exact timing does change throughout the year, you can expect the sun to start setting at around 6.30pm.
Just enough time to fit in a photo shoot before heading out for your evening meal. Our choice for the best sunset destination is Keawakapu beach.
This sprawling beachfront, splashed with golden light, makes a selfie backdrop that’s out of this world. Don’t worry if you can’t get the snap you wanted.
Sunset the next night is sure to be fabulous as well!
Is There Much Nightlife In Wailea?
The laid back Hawaiian lifestyle of Maui tends to see people early to bed, and early to rise.
After a sunset dinner, most visitors tend to be ready to head back to the hotel. After the excitement of a Maui day, you’ll soon understand why.
But in Wailea, it’s a case of low quantity, high quality. Don’t go expecting clubs and dive bars.
Instead, a small selection of classy restaurants and welcoming bars can keep you occupied if you plan on a late night.
What About Kihei Nightlife?
Kihei is the residential neighbor to Wailea, and a good place to look if you want some lively nightlife. Kahale’s is a classic dive bar (their words, not ours), with live music, sport, and an extensive happy hour.
A long beer list will impress bar aficionados. Or try the South Shore Tiki Lounge. The bar’s open until midnight, and you can get some of the best pizza on the island until 10pm.
