This lovely French-style coffeehouse and wine bar would be more suited to New York, if it weren't for the tropical smoothies—ice cold, all-fruit creamy concoctions—that are perfect for a hot Maui afternoon. The organic espressos and killer gourmet cheese plates are a good change from the more typical island offerings, though most people come here for the wines—there are over 80 selections by the glass and an open tasting every Saturday. This cafe is a good place to get a snack (try the delicious salads and sandwiches) after 9 pm, and there's live music with no cover charge (Monday night's open mic can be hit or miss, try Tuesdays for Brazillian jazz). Be warned, this Market Street strip gets a little seedy at night.

This is good as it gets on Maui—a modest Italian restaurant in the little cowboy town of Makawao that turns into a funky bar–disco late at night. The crowd is sometimes very young—mostly early to mid-20s—but it's a sun-kissed and fun-loving scene. It's not a standing around or standing-off kind of place: People get up and dance (albeit to some really predictable music). Ladies Night (currently on Wednesdays, but call to confirm) is the hot ticket—women get in free and visitors (new blood) get a lot of attention.

This divey saloon and pool hall, ceremoniously decorated with pictures of its patron saint, country singer and local resident Willie Nelson (who is rumored to be part owner), throws down a makeshift dance floor on the weekends. It's a haphazard sort of party, but the locals love to let their hair down here, making it the perfect spot to begin an island-style lost weekend. On occasion, Nelson does play here, sometimes with friends like Bonnie Raitt, who might be in town to perform at the Maui Arts and Cultural Center. It's unlikely you'll get into one of these private shows, but just stand in the parking lot for a free concert.

Open Mondays through Saturdays.

This concert series—held every Wednesday at 7:30 pm in the the pavilion at the Napili Kai Beach Resort—has produced three Grammy-winning albums. It's a unique opportunity to hear the best Hawaiian-style slack key guitar musicians perform, and a mellow, romantic alternative to a hectic luau or pick-up bar. Depending on who's playing (look out for Led Kaapana, Dennis Kamakahi, Ozzie Kotani, Owana Salazar, or George Kahumoku, Jr.), it can get crowded, but tickets are generally available the week prior.

Strange but true: A lot of young people from Ireland work on Maui. You can find plenty of them at this popular Irish restaurant and bar (which sometimes morphs into one of the island's more unlikely nightclubs). Every night there's something different, from reggae musicians to Irish folksingers to trance DJs. There is nothing really Hawaiian about this experience, but the crowd is friendly and mixed in almost every way—Irish and non-Irish, 20s to 40s, locals and tourists—and it's a good place to meet people and actually chat.

Open daily 8 am to 1 am.

Timba, an open-air bar and weekend dance club, has brought Maui's nightlife to a new level. Located oceanfront directly above Pacific'o restaurant on Lahaina's Front Street, this modern, one-room hangout has a wood-beamed ceiling and plenty of black and white leather sofas that are perfect for sitting back and surveying the crowd. But the best tables are those on the outdoor balcony with sand and sea views. Thursday nights, you'll find groups gathered for pau hana (after work) drinks. Friday and Saturday nights are more of a raucous pickup scene, when both local and international guest DJs (bigger names on holidays and long weekends) spin hip-hop, house, and soul; the dancing goes on until the wee hours. Finding parking on a busy night is not easy, since the hard-to-navigate garage fills up quickly—between the parking challenges and the cocktails, we recommend calling a cab.—Cathay Che

Open Thursdays through Saturdays 9 pm to 2 am.

Once a staid golf resort, the Hotel Wailea has been born again after a boutique hotel makeover in 2009. Its Friday and Saturday night parties also are a push to attract a younger, sexier crowd, and it works. The lounge is set up inside the hotel's circular, open-air lobby, where the low chairs and tables provide a relaxing perch for taking in the view high over Wailea out to the ocean. The gathering starts around 5:30 pm; be sure to stake your claim before the sun sets (usually between 6:30 and 7:30) for the best mood lighting. The drinks skew tropical—Lilikoi Spritzers (that's passion fruit) and Citrus Mintinis—and are all organic. DJ's Deejays start spinning dance music around 10, and occasionally the music is live, but because this is a small, intimate hotel, shenanigans wrap up promptly at midnight.—Cathay Che

Open Fridays and Saturdays 5:30 pm to midnight.