9 Best Nightlife in Kailua-Kona, Big Island

You know you're in the right place when you climb the stairs to this little gem and notice that the steps are painted like piano keys. With a location in the heart of town, including a perfect view of Kailua Bay, this open-air club presents an incredible variety of music (jazz, Latin, country, classical) and special events such as dance lessons, wine tastings, and themed dress-up parties. One of the proprietors is a renowned jazz musician and plays with his own group or guest musicians. The menu of crepes is straightforward and a tad overpriced. A small cover charge helps pay the musicians a living wage. Note that Gertrude's is closed Monday and Tuesday. 

The only genuine brewpub in Kona, this spot is beloved by locals and visitors alike. Good pizzas and salads, excellent locally brewed beer (go for the sampler and try four of them), and an outdoor patio with live music on Sunday night means this place can get crowded, especially on weekends. The location isn't at all scenic, but that's not the draw of the brewpub. The main entrance is at the end of Pawai Street, in the Old Industrial area.

There's an enticing and creative array of beers, ales, ciders, and hard seltzers at this employee-owned brewing company. Ola Brew is committed to community investment and support of local farmers and merchants. Take a barstool at a picture window facing the main brewing operation and enjoy a fresh, on-tap draft and an appetizer. There's plenty of outdoor seating as well. The taproom menu features reasonably priced tacos, salads, flatbreads, and poke bowls. Ask about their brewery tours. Popular local bands entertain on a regular basis.

Jazz, Island, and classic-rock bands perform here nightly, and outside you may see people dancing in the sand. It's best for a tropical cocktail and an appetizer such as a poke bowl or kalua pork quesadilla. The location, on the waterfront right next to their flagship restaurant, doesn't get any better than this in town. Happy hour is 3 to 5.

Beer lovers appreciate the 36 craft brews on tap at this oceanfront restaurant, with dining downstairs and another bar upstairs that features live music and dancing. It's always busy with young local revelers. Humpy's food can be hit or miss, but it's great for late-hour grill items. Happy-hour specials are available weekdays 3 to 6, and the bar stays open until 2 am.

They call themselves Kona's "dive" bar, but we're not sure we agree. It's fun and kitschy, and locals know this is the best place to dance and drink in Kailua-Kona. With 32 TVs, there's not a sports event you will miss, either.  Sometimes Hawaiian and island music headliners perform here, such as local recording artists Anuhea or Rebel Souljahz. Local musicians with followings also draw their "groupies." After 10, DJs spin tunes on the ocean-breeze-cooled dance floor, located upstairs with killer views of the water. The food is decent and includes full meals, such as cheeseburgers or fish-and-chips.

A popular gathering place, this sports bar in the back of the Coconut Grove Marketplace has a pool table and an outdoor patio, along with dozens of TVs screening the big game (whatever it happens to be that day). It really gets hopping on the weekends and for karaoke on Tuesday and Thursday. There's good happy hour pricing and $3 Taco Tuesdays and Thursdays.

Hidden away in an unassuming strip mall, this is one of the Big Island's most venerable gay bars. Drag shows, hot DJs, live music, karaoke, drink specials, fiestas, and Sunday barbecues are included in the roster of weekly events. All are welcome.