Bill Brooks / Alamy
November 05, 2014

People always wonder where Maui residents go when they take a vacation. After all, where do you go when your home is in paradise? The answer? Las Vegas. The reason? Because Vegas has a degree of rowdy nightlife not found on our small-town shores. Maui, for the most part, goes to bed early, and you’re more likely to find surfers at sunrise than patrons in a bar past midnight. With that said, Maui doesn’t completely fall asleep as soon as the sun goes down, and there are a decent number of evening hot spots that really do let loose—even if it’s just a little bit—when it gets dark.  While you can always check the local community newspapers and posted flyers also can highlight certain events, these are some of the best Maui locations for planning a night on the town. 

Fleetwood’s on Front St.

Bagpipes at sunset kick off the festivities at this rooftop bar by Mick Fleetwood. The legendary drummer can make impromptu appearances and jump right in with the band, and there is live music every night with a view looking over Lahaina. Bands usually finish by 9:30 pm, so don’t expect to stay late. Instead arrive early for $5 wine tastings beginning at 5pm. 

Maui Arts and Cultural Center

You never know what big name act will be playing in Maui when you visit. Artists from The Eagles to Elton John have performed here at “the MAAC,” and the lineup of concerts and live performances is constantly packed with talent.  You can also find plays with Broadway-quality actors as well as hula performances and film festivals, and this is a facility you’d expect to find in New York as opposed to little ‘ole Maui.  

Casanova’s

Bongo drums, wine carafes, salsa dancing, rhythmic house, and a Wednesday evening “Ladies Night” that is the hottest night on the island. Whereas other nightclubs have come and gone, this Makawao discotec has consistently remained sexy and is brimming with beautiful guests. Fridays and Saturdays have visiting DJs or live reggae and Latin, and there is even a shuttle for Ladies Night that picks up from the Wailea resorts.

Charley’s

It’s been known as “Willie Nelson’s place,” but you never know what A-list celebrity might be laughing and drinking at Charley’s. The vibe here is decidedly casual and completely unpretentious, and everyone who walks through the swinging front door is just here to hear some good music. You can find live bands on most nights of the week—mostly acoustic and rock—and this is the most happening bar in funky Pai‘a—one of the happiest towns in America. 

South Shore Tiki Lounge

Maui has a rule that prohibits dancing in an establishment without a dance floor (weird, we know). Luckily, not only does the “Tiki Lounge” have a proper dance floor for partying, but it’s usually packed with everyone in South Maui looking to tie one on. Late night DJs and evening drink specials help to keep the party going until closing at 2 a.m. 

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