The majority of Kihei’s nightlife takes place at The Triangle, as in, The Barmuda Triangle, where you could end up getting lost for days. This collection of bars within the Kihei Kalama Village can almost seem like a tropical frat row with each house on the street having a different theme party.
If you’re starting your night early, check out Haui’s Life’s A Beach (1913 S. Kihei Rd., 808/891-8010, until 2am daily), aka The Lab. This rockin’ beach bar has an outdoor patio that looks toward South Kihei Road and is a great place for people-watching. There is live music most nights, or you can shoot some pool, watch some sports, and eavesdrop on local happenings.
The best venue within the Triangle for live music is Three’s Bar and Grill (1945 S. Kihei Rd., 808/879-3133, until 1:30am daily), a semiformal dining establishment that also has a VIP Surf Lounge with a built-in stage area and lighting. Weekdays often have music around dinner time, and weekend shows begin around 10pm and usually stretch until closing.
The most popular club in the traditional sense of the word is the South Shore Tiki Lounge (1913 S. Kihei Rd., 808/874-6444, until 2am daily), where resident DJs play for a small but crowded dance floor. This place gets popular on weekends with its thumping house beats and young singles.
Across the parking lot, swap your draft beer for some cutting-edge mixology at Ambrosia (1913 S. Kihei Rd., 808/891-1011, until 2am daily), a small martini bar that specializes in “upscale drinking.” DJs spin on many nights of the week, and the vibe is decidedly classier and more refined than at some of the neighboring venues.
For an authentic dive bar—not the fashionable kind—Kahale’s Beach Club (36 Keala Place, 808/875-7711, until 2am daily) is a working-class bar with live music, cheap drinks, and a decidedly local atmosphere. The beer is some of the cheapest on the island, and you won’t find grass skirts, convertibles, or timeshare salespeople within a respectable radius.
Finally, for a good old-fashioned touch of the craic, Dog and Duck Irish Pub (1913 S. Kihei Rd., 808/875-9669, until 2am daily) is a small gathering place where you can throw darts, eat bangers and mash, drink Guinness, rock out to live music, or take part in the popular quiz nights. To switch up the drinking venue, right next door is the recently opened What Ales You (808/214-6581, 11am-10pm daily), a small tap house with 16 beers on tap and about 20 wines on the wine list.
Outside the Triangle
Down at the other end of the parking lot of the Azeka Mauka is Diamonds Ice Bar (1279 S. Kihei Rd., 808/874-9299, open until 2am daily), a small establishment tucked in the end unit that offers live music most nights. If you have a large group, there’s a private VIP room. While it doesn’t see the same amount of crowds as down at the Triangle, it can still be a happening place if the right band is playing.
Moose McGillicuddy’s (2511 S. Kihei Rd., 808/891-8644, open until 2am daily) harnesses the late-night crowd in South Kihei who are looking for cheap drink specials and an old-fashioned good time. This sports bar cranks up the music at 9pm and caters mostly to the single crowd that’s looking to get a bit weird.