Gertrude’s Jazz Bar

Big Island Guide Travel Guide

One of the best music scenes on the Big Island, Gertrude’s Jazz Bar is known for high-end cocktails, classic comfort foods, and a vintage atmosphere, all in an open-air, tropical setting. With the Pacific Ocean breezes gently drifting from stage left, and live jazz playing almost every night, Gertrude’s Jazz Bar is treasured for its food, cocktails, talented musicians and wonderful 1930’s vibe fused with a tropical twist.

The club debuted in 2016, and is the creation of artists Marlina Lee, Greg Shirley and Kira Kamamalu. In search of an island lifestyle, Marlina moved to the Big Island in 1979 from California and Greg from California and Washington state in 1999. The two met at a Tango Geisha Dance event at Kona Coffee and Tea and that’s when the music started.

Located along Ali’i Drive in historic Kailua Village, once a fishing community and retreat for Hawaiian royalty, Gertrude’s is a zenith of culture, art, music and dance. Marlina had always wanted to open a bar but not a ‘typical’ one and Greg always wanted to open a jazz club. When Greg saw that the location was available, united with Marlina knowing the building’s owner, it was Gertrude’s at first sight!

As you enter the second story oasis, you feel transported to a sexy, jazz club along Bourbon Street in the heart of New Orleans’ historic, French Quarter. It’s no wonder why they named their club after Gertrude Stein, and her Paris salon, where leading figures in art, literature and music flocked. Pablo Picasso, Henri Matisse, Ernest Hemingway and F. Scott Fitzgerald all sat at her round-table. As an American in Paris in the 1920’s, she was considered the “mother hen” of leading art figures during the modernism era.

Gertrude’s vintage, inspired interior is graced with original art work by Marlina’s daughter Kira Kamamalu, who also coordinates all of Gertrude’s art events and openings. Kira’s renditions in oil capturing subjects in muted colors, light and shadows are reminiscent of the great Impressionists.

Both Marlina and Greg have a long-established kinship in the arts: Marlina is a dancer and Greg is a musician. While you are savoring Angles on Horseback and sipping a Picasso Espresso Martini, you may see Greg playing the bass, then later, dancing the Tango with Marlina “cheek to cheek”, like Fred Astaire and Ginger Rogers!

The joys of owning Gertrude’s is the “opportunity for musicians to play, where dancers can dance and learn how to dance and for new artist development.” Surprise guest musicians who have graced Gertrude’s center stage are notables such as guitarist, Bruce Foreman who performed with Ray Brown and Eddie Duran and Manhattan jazz singer, KT Sullivan who has performed at the Laurie Beechman Theater and the Oak Room at New York’s Algonquin Hotel.

If you’re looking to take a load off your feet from dancing, delight in Gertrude’s culinary offerings and libations. When selecting items for the menu, guided by an award-winning chef, Marlina, Greg and Kira curated a menu of delicious comfort foods such as: sweet Potato Daupine (Okinawa Potato), Cha Cha Chorizo Mac & Cheese (aged gouda, asiago cheese and double crème), New York Steak, Scallops and those aforementioned Angels on Horseback (applewood bacon-wrapped dates, stuffed with crème de gorgonzola).

Gertrude’s House Libations are created by Eileen Harrington, all home-made and hand-squeezed such as the Ginger-Lychee Caipirinha (Brazilian Cachauca, fresh lime and lychee); the Hemingway Whiskey Smash (Buffalo Trace Kentucky Bourbon, fresh mint and lemon) or The Green Fairy, the non-conventional vehicle for artistic transformation made with La Louche Absinthe.

Marlina, Greg and Kira have “raised the bar on bars, creating an adult, classy atmosphere with live music, real musicians and no machines.” To explain Gertrude’s Jazz Bar to someone who has never experienced it, “Gertrude’s is a place to experience live, danceable music in an oceanfront, artistic atmosphere, enjoy hand-crafted cocktails and classic, comfort foods.”

Closed on Mondays, Gertrude’s has theme nights throughout the week, as well as, special events at the jazz bar including such recent favorites as: Kahulanui Hawaiian Swing, Spirits of Aloha, and Midnight in Paris. Gertrude’s also hosts an ‘after-hours happy hour’ on Friday and Saturday starting at 10:00pm and is looking at possibly adding a Karaoke night in the future.

Gertrude’s regular schedule is also chock-full of entertainment including partner dance nights, open mic nights that feature local artists as well as new talent, Latin nights with live music, live jazz, dance lessons, art events, and even comedy nights.

As the music of Gertrude’s Jazz Bar echoes through Kailua Village’s historic avenues across the rippling tides of Kailua Bay, artists congregate celebrating self-expression, making this one-of-a-kind establishment an atmosphere for which even Gertrude Stein would say, “Ooh La La!”

Events Nights at Gertrude’s

6:30pm – 9:30pm
Live Jazz – Guitar or Piano Jazz for Dancing

6:30pm – 9:30pm
Jam Night, Comedy Night, Art Events

6:30pm – 9:30pm
Live Music – Latin Dance Night

6:30pm – 9:30pm
Live Music – Jazz, Blues or Rock

6:30pm – 9:30pm
Live Music – Jazz, Blues or Rock

5:00pm – 8:00pm
Live Music – Jazz, Hawaiian Swing, Jam…

Business Hours
Tues-Sun 5-10:30pm
Closed Mondays
Wed 9am-1pm Boat Day Brunch

Average Dining Pricing

(808) 327-5299

75-5699 Alii Dr
Kailua-Kona, HI 96740

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