Gertrude's Jazz Bar - Hawaii Restaurant
#41 of 199 Restaurants in Kailua

Gertrude's Jazz Bar

4.4(115 community reviews)
Fine Dining ($$$$)

About

Discover Gertrude's Jazz Bar, offering the best Dining bars experience in Kailua-Kona. Enjoy Fine Dining ($$$$) meals, explore their menu, and read reviews from the community on TasteHi.

Sway to the Rhythm in the Heart of Kailua-Kona

When the sun dips behind the Pacific horizon, the scene at Gertrude's Jazz Bar in Kailua-Kona shifts from sleepy coastal town to a vibrant hub of rhythm and brass. This is where local musicians and traveling jazz enthusiasts converge. Stepping through the doors, you are immediately hit with the unmistakable scent of well-loved hardwood floors and the crisp, lingering notes of a saxophone solo echoing off the walls.

The Pulse of the Kona Nightlife

Unlike the tourist-heavy luaus that dominate the Big Island after dark, Gertrude's offers a refined, intimate escape. It feels like a secret found in the back alleys of New Orleans, but with a distinct island soul. The acoustics are sharp, allowing every pluck of an upright bass to resonate through the dimly lit room. Expect a crowd that appreciates the craft; you will find locals nursing craft cocktails while bobbing their heads to live sets that often feature island-inspired improvisations.

A Few Things to Keep in Mind

The space is cozy—some might even say compact. On busy nights, finding a seat can be a bit of a dance, and the proximity of the tables means you might end up making friends with your neighbors whether you intended to or not. It is loud, unapologetically so, and the energy is infectious. If you are looking for a place to hide away in silence, look elsewhere, but if you want to immerse yourself in the authentic nightlife scene of the Kona coast, this is the destination.

What to Expect

The bar menu leans heavily into classic spirits and signature house cocktails that cut through the humidity of the evening. It is the perfect stop for those who value musicianship over glitz. Whether you are catching a local band or a touring artist, Gertrude’s remains a cornerstone of the Kailua-Kona music circuit, providing a rare venue where the music takes center stage every single night.

Location

75-5699 Alii Dr, Kailua-Kona, Hawaii, 96740-3112

Directions

Reviews

Showing 10 of 115 community reviews
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Jasmin McCGoogle Maps

Recently

Sam’s is Kona’s very own longtime Cheers… where everybody knows your name. The owner puts so much thought and attention into events like holidays, customers birthdays or food contests. Also they have great food vendors just outside their bar. Also if you purchase 2 drinks you can get parking validated!

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B BGoogle Maps

Recently

Whether you are a local or a day tripper Sam's Hideaway is the place to hang out for good bartenders, well mixed drinks, and friendly patrons. Josh does a great job behind the bar. Friendly, professional and helps the patrons mingle. BTW, best drink prices on the Kona coast. You can't go wrong.

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Tiarhaillson WGoogle Maps

Recently

Had so much fun here! Went on a Monday night and jammed out until midnight! Super friendly atmosphere! The Karaoke Dj was extremely friendly and so welcoming! If you’re looking for somewhere that is chill and overstimulating this is your spot! Very reasonably priced as well which is a plus! 5 stars! Thank you for a great time on vacation!

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Sam CarettiGoogle Maps

Recently

Great to work with for our wedding after party. We had so much fun. Mike was great behind the bar and the karaoke DJ kept the party going throughout the night!

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Bailey LankfordGoogle Maps

Recently

Best bar in Kona! Great atmosphere and the best vibes. I tried going to other bars on different nights but somehow always ended up back at Sam’s Hideaway. I went multiple times during my week-long trip! DJ Kyleigh was my favorite of all the DJs—she had the best energy and made the nights so fun. I’m already missing Sam’s Hideaway and can’t wait to get back to Kona!

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Mark BrostowitzGoogle Maps

Recently

Stopped in on Monday at 3 PM for two draft beers and a club soda for my wife. Tab was $17, and the CS was free. My 14 ounce draft beer was Kona Brewery at $8.25 per beer. While the glass looked like a pint, it had a 1/2 thick glass bottom, which means it only holds 14 ounces. Wow! As we left, my wife pointed out we probably got the cruise ship price - there was a ship in the bay... We're here for six more weeks and I'll be visiting other places for a reasonably priced beer.

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Gillian WardGoogle Maps

Recently

Sam’s is our favorite place to go! The service is always top notch, karaoke is always a blast, and they keep the place so clean. My tab after a full night there is only ever like 30-40 dollars, I’m always stunned! We love our KJs, bartenders, and security guys. Thank you Johnny, Smiley, Mike, Mike, Micah! And thank you Jeffers for the amazing hot dawgs outside!

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Asia EllisGoogle Maps

Recently

I went here for karaoke, and had to end up asking for my money back because they never played my song. It kept getting more and more songs placed in front of it until I ended up last in the queue and stayed last. Every single song that signed up after me got put in front of me. I waited almost two hours to sing, and my time never came. And you know what, I honestly believe it never would have come. I ended up asking for my money back and said my song keeps getting put at the end and the guy just smirked at me and he handed my cash back. I walked out and I’ll never go back. I’ll never recommend this place ever. If you want to control what music gets played at your bar then hire musicians. You want to force someone out rudely because you don’t like the song they want to sing? Well that kind of makes you a….. well you know what.

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Levi EllisGoogle Maps

Recently

Followed my wife here for Karaoke. She paid to sing a song. She wanted to sing a song by Adele. For some reason the DJ decided he was going to keep her song at the very end of the queue and never let it come up. We kept looking at the queue and everyone else's songs kept butting in line. Totally lame. We talked to the guy and he didn't say anything. Just gave us our money back. No explanation. Not sure why we were discriminated against. Maybe because we were white? I don't get it. She's a performer. She's actually a really good singer unlike what you see at most karaoke bars. So we just left. Wife was super bummed.

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J'oni SmithGoogle Maps

Recently

So fun! Local man took us there. Had a blast! Great drinks and prices. Don't go to the restroom! You have to walk past shops with adorable clothing and stuff. Came back to bar in my new dress🤣🤣🥂🌴🐬

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Frequently Asked Questions about Gertrude's Jazz Bar

Common questions from diners about Gertrude's Jazz Bar in Kailua-Kona.

Yes! Gertrude’s Jazz Bar is proud to offer a variety of vegetarian, vegan, and gluten-free dishes on our tapas and dinner menu.

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