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Welcome to the definitive list of the best Wailea happy hours for 2020. Relax in the comfort of your resort or venture out to explore some of the happy hour deals in Wailea.

7 best Wailea happy hours (2020) are the following based on Yelp reviews, TripAdvisor reviews, and our local research and opinion:

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.

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!

$4.50 draft beers from 3:00 to 6:00 pm makes this the place to go for a cold one. Longhi’s offers a solid happy hour beer selection with Maui Brewing Bikini Blonde, Peroni, Deschutes Season Ale, and Corona Light. A good mix of light beers for early drinking in the Maui sun.

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 $10 cocktail. They back this up with an $8 Maui Mule, $7 island-style margarita, and $6 well drinks. The Pint & Cork bartenders know how to mix a drink so you won’t be disappointed.

Pint & Cork in The Shops at Wailea has an extensive cocktail menu with top-notch bartenders.

Pint & Cork in The Shops at Wailea offers the [/caption]

Monkeypod Kitchen Wailea delivers with 50% off their entire appetizer menu. They also offer their kiawe wood oven pizzas for $10. Happy hour is 3:00 to 5:30 pm and 9:00 to 11:00 pm so you have two shots at this happy hour fare. 

The competition is fierce as all lanai’s point west in Wailea. Gannon’s Restaurant won this happy hour competition with the views from The Red Bar. With a happy hour from 5:00 to 8:00 pm, you can relax before the sun goes down and then continue partying. 

Perched high up on the hill compared to the resorts, Gannon’s gives you a sunset view you will remember. Come early to get a seat.

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 7 list below for more details on these fine establishments. 

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 7 happy hour list, you will find the current Yelp ranking, TripAdvisor ranking, results of our personal research, and our final consolidated ranking.

Our review looks at the following criteria to determine the best Wailea happy hours.

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 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

We update this list monthly to reflect the trends, user input and evolving happy hour deals. Evolution is key to happy hour reviews so we welcome comments and updates. Email me or leave a comment below on your happy hour experience.

Erica, a member of our Wailea Happy Hour Expeditionary Forces enjoying the sun before heading into Tommy Bahama’s.

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 month when we send them out into the wilds of the Fairmont Kea Lani Wailea again. 

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 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 many locals drinking around Wailea. Head over to Kihei or Lahaina to check out the local happy hour scene. 

Planning on visiting Lahaina? Check out our 10 Best Lahaina Happy Hours list.

(With the exception of poke tacos, raw bar & lobster deviled eggs)

$10 Pizzas

(With the exception of the bourgeois pizza)

(see the happy hour menu section)

Check out their happy hour live music calendar

Yelp: 1

TripAdvisor: 1

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

Located at the main entrance to Wailea sits Monkeypod Kitchen. You can’t and shouldn’t miss it.

(excluding Dec 23rd – January 1st)

(see the happy hour menu below)

(Check Gannon’s music calendar for details)

Yelp: not ranked

TripAdvisor: 4

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 prepared by the owner and chef Beverly Gannon. Fine dining with a view is what they aim to deliver.

Come early to get a seat on the lanai in The Red Bar 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. With a happy hour from 5:00 to 8:00, you will have primo seats for the sunset. 

The appetizer menu is extensive and includes some of Beverly’s favorites. 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 Gannon’s up on a bluff overlooking the Pacifica Ocean at 100 Wailea Golf Club Drive. 

Website: Gannon’s Restaurant 

Yelp: 13

TripAdvisor: 2

Vibe: People are crazy about Tommy Bahama’s happy hour. Tommy Bahama’s knows how to create an island-vibe even while being located 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 (above Longi’s)

Website: Tommy Bahama’s Restaurant and Bar

(see the happy hour menu below)

Yelp: not ranked

TripAdvisor: 3

Vibe: Take advantage of the large patio sitting and open-air bar to enjoy happy hour at Longi’s. A touch of old-world Italian ambiance set in a Maui garden. The ambiance is relaxing and the breeze is good but there are no ocean views. Their landscaping makes you feel like you are in a tropical garden instead of next to a parking lot in a shopping center.

Longi’s offers great happy hour prices and they put some of their best Italian pupus on their large happy hour pupu menu. If you are craving Italian in Maui, this is the classic place to go. Get a good deal while going during happy hour. 

Longi’s is below Tommy Bahama’s so check them both out. Cheeseburger in Paradise is also a stone throw away (literally).

Location: The Shops at Wailea, 3750 Wailea Alanui Drive

Website: Longi’s Wailea

(see the happy hour menu below)

Yelp: 3

TripAdvisor: 6

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 come 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

With a great food menu, kids are welcomed at Pint & Cork.

(see the happy hour menu below)

Yelp: 4

TripAdvisor: 8 

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 $10. 

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

Yelp: 2

TripAdvisor: not ranked

Vibe: This hotel bar has a cult following. Mainly frequented by Fairmont hotel guests, the service and the sunset view brings people back throughout their stay. It is probably why they dropped their sunset happy hour. The later happy hour is still in full effect and ever-changing to keep it fresh.

LUANA dropped its early happy hour so now they only offer the 8:00 to 10:00 pm happy hour. The specials are good and add in the Friday events, you are guaranteed to have a good time.

The friendly bartenders, complimentary bar snacks, and good food make this place worth a trip. Sit out on the lanai and enjoy a nice night-time happy hour. 

The happy hour and events menu change frequently so check-in here updates or call ahead to confirm the happy hour specials. 

Location: Located at the Fairmont Kea Lani at 4100 Wailea Alanui Drive.

Website: LUANA Bar Wailea

Directory of the happy hour drinks and food menus specific to our top 7 Wailea happy hour list. Click the link to see their menu.

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. Read about it in our Ultimate Maui Food Truck Guide.