6 Best Wailea Happy Hours
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Welcome to the definitive list of the best Wailea happy hours. Relax in the comfort of your resort or venture out to explore some of the happy hour deals in Wailea.
The 6 best Wailea happy hours are the following based on Yelp reviews, TripAdvisor reviews, and our local research and opinion:
- 1. Monkeypod Kitchen Wailea Happy Hour
- 2. Gather on Maui Happy Hour
- 3. Tommy Bahama’s Restaurant Happy Hour
- 4. The Pint & Cork Happy Hour
- 5. Humble Market Kitchin Happy Hour
- 6. Oao Sushi Bar & Grill
The beaches on the south side of Maui aren’t the only reason to leave the resort. Grab your sandals, take a stroll, pull up a chair, and enjoy a sunset with the best drink and appetizer (pupu) specials in Wailea.
Trust that you are in good hands as our team personally sips, dips, and whips up the best happy hour reviews across Wailea and the rest of Maui.
Find the place that fits your vacation vibe or discover where the locals go to pau hana.
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Find the best south Maui beaches, and don’t miss the best snorkel spots on Maui
Looking to fill up your time in Wailea? Check out our favorite things to do in Wailea. If you’re up for adding Kihei, we have 15 more things to do there!
Best Wailea Happy Hours by Category
Not everyone is looking for the cheapest pint of beer for happy hour. We extract the favorites by category so you can pick them yourself. Happy hour is fleeting, so pick your place and get out there!
Best Happy Hour Drink Specials – The Pint & Cork
The Pint & Cork offers the best price and best selection for happy hour cocktails from 2:00 to 5:00 daily. $3 off their signature drinks makes for a competitive $13 cocktail. They back this up with an $8 Island Time Mule, $8 Mid-Day Margarita, and $7 well drinks. The Pint & Cork bartenders know how to mix a drink so you won’t be disappointed.
Best Happy Hour Food Specials – Monkeypod Kitchen Wailea
Monkeypod Kitchen Wailea delivers with 50% off their entire appetizer menu. They also offer their kiawe wood oven pizzas for $13. Happy hour is 3:30 to 5:00 pm, they’ve shortened it in the past few years, which is a bummer but their prices can’t be beat.
Best Sunset Happy Hour Wailea – Humble Market Kitchin
The competition is fierce as all lanais point west in Wailea. Humble Market Kitchin won this happy hour competition with the latest happy hour. With a happy hour from 5:00 to 6:00 pm, you can catch the beginning of the sunset while still enjoying discounted prices.
Best Happy Hour Vibe Wailea
Roy Yamaguchi knows how to throw a party. I find his restaurants are always buzzing. Roy’s Humble Market Kitchin will put you in the festive happy hour mood. As the happy hour gets rolling, people pack in to enjoy the drink specials and Asian fusion appetizers. You will leave with a smile on your face.
See our top 6 list below for more details on these fine establishments.
Best Wailea Happy Hour Ranking System
Our lawyers won’t let us disclose our proprietary algorithm for consolidating ratings from across the internet, local input, and the grunt work of happy hour field expeditions.
As a rating consolidator, we are the Rotten Tomatoes of Wailea happy hours. In our top 6 happy hour list, you will find the current results of our personal research and our final consolidated ranking.
Our review looks at the following criteria to determine the best Wailea happy hours.
- Time and duration of the happy hour
- Drink specials
- Appetizer (pupu) specials
- Service with smile
- Quality of the food and drinks
- Live music or other activity
- Vibe
The vibe is the personality of the place during happy hour. Happy hour vibe is different for everyone. One could be looking for a place Captain John Sparrow can be seen, white table clothes to hold your pupus, or a place to watch UFC with locals.
We don’t rank one vibe over another, but we expect the place to have a personality and not be a beige corporate restaurant decorated with pineapples and hula skirts.
We use crowdsourcing to minimize our biases. Adding our two cents to the crowdsourced results provides our local opinion and minimizes the giddy reviews over someone’s first Lava Flow at a swim-up pool in Wailea
Evolution is key to happy hour reviews so we welcome comments and updates. Email us or leave a comment below on your happy hour experience.
Geographic Location for Wailea Happy Hours
Wailea is on the southside of Maui. It is home to the most beautiful, luxurious resorts on Maui. Our Happy Hour Field Expedition Team stuck to the direct Wailea area, namely the resorts, The Shops at Wailea, and the immediate hills over Wailea.
Update, the Happy Hour Field Expedition team returned in one piece from their happy hour crawl. Best of luck to them next time when we send them out into the wilds of the Fairmont Kea Lani Wailea again.
Best Happy Hours in Wailea
You have two main choices when it comes to happy hours in Wailea.
One option is to frequent one of the many bars and lounges in your resort. We didn’t review all of the resorts’ bars as they are as bountiful as they are relaxing. We focused on fan favorites.
The places locals make the trip out to enjoy the happy hour, and where hotel patrons return for happy hour and not the room.
The second option is to venture over to The Shops at Wailea. While a mall leaves much to be desired on Hawaiian culture and atmosphere, the restaurants do a good job of creating an island vibe with good specials. There are also free activities at The Shops at Wailea like coconut husking, hula dancing lessons, Hawaiian shows, and other activities to keep you culturally entertained.
You won’t find dive bars and herds of locals drinking around Wailea. Head over to Kihei or Lahaina to check out the local happy hour scene.
1. Monkeypod Kitchen Wailea Happy Hour
| Time | Drink Specials | Appetizer Specials | Events |
| Daily, 3:30 to 5:00 pm | $2 off draft beers $3 off wines by the glass $4 off cocktails | 50% off appetizers (with the exception of seafood) $13 Pizzas (with the exception of the bourgeois pizza) (see the happy hour menu) | Daily live music at 1:00, 4:00 and 7:00 Check out their happy hour live music calendar |
Vibe: Monkeypod Kitchen in Wailea is a Merriman property. The place rides the line of a beige corporate restaurant but doesn’t cross it. The massive bar, amazing skylight, and ocean views make for a relaxing and pleasant happy hour with the family and close friends.
While the menu is on the $$$ scale, they manage to knock off a healthy amount to bring a smile to your face for happy hour. 50% appetizers and the festive live music made this place worth going to on an afternoon happy hour.
Location: On the left-hand side when you are entering Wailea, in the Wailea Gateway Center. The address is 10 Wailea Gateway Pl, Kihei, HI 96753.
Website: Monekypod Kitchen Wailea
2. Gather on Maui Happy Hour
| Time | Drink Specials | Appetizer Specials | Events |
| Daily, 3:00 to 5:00 pm | $10 signature cocktails $8 classic cocktails $8 wines by the glass $6 draft beers | $12+ app menu (see the happy hour menu) | Live music Sunday nights (Check Gather on Maui’s music calendar for details) |
Vibe: The place can get popping during the summer happy hour. Locals and tourists flock here for the sunset view and the classic Hawaiian dishes. Fine dining with a view is what they aim to deliver.
Come early to get a seat on the lanai for happy hour. They share the same lanai as the dining room so you are not missing much by going to happy hour over dinner.
As a $$$ place, the happy hour specials are a great way to enjoy one of the best, if not the best sunset views on Maui.
Warning: Check their website as they do close for private events on a rare occasion. You don’t want to make the drive up the volcano to be turned around thirsty.
Location: Billed as the best view on Maui (a big claim), you can find Gather on Maui up on a bluff overlooking the Pacific Ocean at 100 Wailea Golf Club Drive.
Website: Gather on Maui
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3. Tommy Bahama’s Restaurant and Bar
| Time | Drink Specials | Appetizer Specials | Events |
| Daily, 2:00 to 5:00 pm | $10 – $11 wines $12 for 4 of their signature cocktails $13 martinis, 4 to pick from $7 select draft beers | $12 – $14 pupus, 6 to pick from | Live music starts at 5:00 pm, after the happy hour. |
Vibe: People are crazy about Tommy Bahama’s happy hour. Tommy Bahama knows how to create an island vibe even in a shopping center.
The food and the drop-dead delicious cocktails bring people back. I like the open-air bar that overlooks the treetops to enjoy their signature martinis.
The happy hour promotion is for the bar top only. If you are in a large party or the bar top fills up, they will oblige with island hospitality to have you sit on the lanai.
Location: The Shops at Wailea, 3750 Wailea Alanui Drive.
Website: Tommy Bahama’s Restaurant and Bar
4. The Pint & Cork Happy Hour
| Time | Drink Specials | Appetizer Specials |
| Daily, 2:00 to 5:00 pm | $3 off signature cocktails 20% off wines by the glass $1 off draft beers $8 margarita $7 well drinks $1 off bottled beer selection | $7 to $12 pupus include deviled eggs, soup, chicken wings, and mac & cheese $5 sliders (see the happy hour menu) |
Vibe: A friendly tavern with some personality compared to the other places in The Shops at Wailea. Featuring 8 large screen TVs, the sports fans flock here on game day. There is no outdoor seating but the atmosphere inside will warm you up.
The Pint & Cork comes ready to play by slashing dollars off their menu for happy hour. As a quality gastropub, their happy hour appetizer menu is worth ordering a few items.
Wash it all down with a large selection of draft beers and signature cocktails to make an afternoon of it while at the shopping center.
Family is welcomed but there is not a lot of room for the kids to run around.
Location: Inside The Shops at Wailea, 3750 Wailea Alanui Drive.
Website: The Pint & Cork
5. Humble Market Kitchin Happy Hour
| Time | Drink Specials | Appetizer Specials |
| Daily, 5:00 to 6:00 pm | $8 draft beer $10 well drinks $12 wine by the glass $14 specialty cocktails | $12 appetizer menu includes brussel sprouts and cauliflower, steamed dumplings, calamari, and chicken wings (see the happy hour menu) |
Vibe: A festive and lively restaurant and bar by Roy Yamaguchi. Get a view of the sunset from the same perspective as a palm tree on Humble Market Kitchin’s lanai. Come early to grab one of the few seats on the lanai for a happy hour.
Inside the place gets a little busy and loud for a relaxing happy hour but should all happy hours be relaxing? Feel the energy of the room and enjoy Roy’s humble Maui happy hour appetizers that are a good deal at $12.
The happy hour drinks, service, and ambiance never disappoint but Asian fusion food can be hit or miss. Perhaps it is best to try it out for a happy hour before committing to staying for dinner once the sun slips below the horizon.
Location: Located at the Marriott Wailea Beach Resort at 3700 Wailea Alanui Drive.
Website: Humble Market Kitchin
6. Oao Sushi Bar & Grill
| Time | Drink Specials | Appetizer Specials |
| Daily, 12:00 to 5:00 pm | $6 – $7 beers $12 cocktails $10 – $12 wine $18+ sake | $8 – $13 most small plates $7+ sushi |
Vibe: The vibe here is very casual and laid-back, exactly what many are looking for when they seek out a happy hour (or five!). While it lacks lanai seating with ocean views, it makes up for it with a large happy hour menu, great food, excellent service, and a 5-hour happy hour!
Oao (pronounced “wow”) is a newer restaurant that opened its doors in late 2022 and boasts the longest happy hour in Wailea. This is definitely a pricey spot, so the extended happy hour with 30% discounts are a warm welcome, as is the large happy hour food menu!
Since the restaurant is relatively new, we’re excited to see how its cocktail menu expands. Stay up to date by visiting the restaurant’s Instagram page.
Location: Located in the Wailea Gateway Center at 34 Wailea Gateway Pl, Kihei, 96753.
Website: Oao Sushi Bar & Grill
Wailea Happy Hour Menus
Directory of the happy hour drinks and food menus specific to our top 6 Wailea happy hours list. Click the link to see their menu.
- 1. Monkeypod Kitchen Wailea Happy Hour Menu (page 5)
- 2. Gather on Maui’s Happy Hour Menu
- 3. Tommy Bahama’s Restaurant Happy Hou
- 4. The Pint & Cork Happy Hour Menu (scroll down for the happy hour)
- 5. Humble Market Kitchin Happy Hour Menu
- 6. Oao Sushi Bar & Grill (full menu is pinned on their Instagram)
After happy hour drinks, have a designated driver take you to dinner in Kihei. We recommend the food truck park for the best local cuisine. If you’re more in the mood for a sit-down restaurant, check out our favorites in Kihei and Wailea.
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Hawaiian Island Cheat Sheets
Sign up & we’ll send you our island cheat sheets so you can get to know the islands like the back of your hand!
We’ll share 4 can’t-miss activities on each island, a map with the main sights in town, & famous local grindz (eats)!
