Take a Sip at 15 Extraordinary Bars in Oahu, Maui & the Big Island

Maria Jordão

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Take a Sip at 15 Extraordinary Bars in Oahu, Maui & the Big Island

If you’ve just landed in the paradise that is Hawaii, or even if you’re just getting started on planning your dream trip to this destination, then this article is for you. When you think of Hawaii the first thing that probably comes to mind are the pristine clear waters, endless patches of sand that looks like brown sugar, and rocky mountains covered in greenery. There are many miles of natural landscapes to explore, and outdoorsy activities to try like diving, surfing, and hiking. And then there’s the cocktails. We’re talking about the real deal, Hawaiian cocktails in Hawaii. We’re sure you’ll end up enjoying at least one of these world-famous beverages by the beach or at a casual bar even if you’re not a cocktail or mocktail fan.

After a long day of adventuring, you’ll need a well-earned unwinding in one of Hawaii’s dream-like beaches while sipping on a refreshingly fruity cocktail. And when the sun starts to dive into the Pacific, it’s time for the Hawaiian night to come to life. Exploring the local nightlife is considered one of the ways to get to know the location you’re traveling to, and Hawaii is no exception. From a tropical drink served in half of a pineapple, unique local brews you won’t find anywhere else to live music at a bar that’s literally on the beach, there’s a whole world of drinks and bars for you to discover.

If this has piqued your interest, and you’re the type of traveler that wants to have their cake and drink it too—pun intended—then embark on a journey with us through the best bars and drinks in Oahu, Maui and the Big Island. Who knows, you might even end up making your own home-made cocktail while listening to some Jawaiian music—a mix of Hawaiian sounds and some Jamaican reggae.

Mai Tai by Merriman's Outdoor Grill in Maui.JPG

Maui's Merriman's Outdoor Grill Mai Tai Cocktail by @cafesandcocktails

Bars in Oahu Island

Mai Tai Bar - Ah, the famous Mai Tai. Did you know the first time this tropical drink was served was in 1953 at the Mai Tai Bar? It’s the ideal spot to sip on a tropical cocktail with a tiny umbrella on it or, if you’re feeling extra fancy, enjoy your drink served in a Maui Gold pineapple.

Duke’s Waikiki - At Waikiki Beach, right on the edge of the sand, you’ll find this bar. Its name was given to honor Waikiki’s surf legend Duke Kahanamoku, and inside the bar, you’ll find a raft with some of his treasured objects. You won’t be able to leave without trying their signature Duke’s Mai Tai!

RumFire - Imagine a stunning sunset, you in a waterfront bar, and a tropical drink in your hand. Sounding pretty good yet? At RumFire bar you’ll find liquid Aloha cocktails, Sangria Carafes, local beers & wines, all while you admire the ocean view.

Sky Waikiki - From the top of a 19-story building known as the Sky Waikiki lies Oahu’s most mesmerizing view. You can just sit back and relax on their rooftop with a glass of a signature cocktail in hand. Gaze upon the most picturesque sunset and the clearest blue waters you’ve ever seen and enjoy their daily live music.

La Mariana Sailing Club - Looking for a 1950’s vibe? Then La Mariana Sailing Club is up your alley. This retro bar is just the spot for all you old-schoolers out there. Inside you’ll find tiki torches and nostalgic memorabilia. Plus, someone will be sure to tell you that the original Hawaii Five-0 was filmed right where you’re standing! 

Duke's Waikiki, Oahu Island.jpg

Duke's Waikiki, Oahu Island by @hehunakai

Bars in Maui Island

Tiki Bar & Grill - When you think Tiki Bar, what comes to mind? Lined coconut trees, Hawaiian-print shirts, and ukulele music playing in the background? Well, that’s exactly what you’ll find at Tiki Bar & Grill. A few steps away from the beach and just over by the poolside, enjoy a fruity cocktail over happy hour while you listen to some live ukulele every day.

The Dirty Monkey - If you’re a true happy hour fan, then Dirty Monkey is one of the bars in Maui Island you have to visit. Considered one of the best spots to enjoy a great happy hour, every day from 3 to 6 pm you’ll be able to enjoy Mai Tai’s, tropical cocktails, and local draft beers.

The Pint & Cork - With an extensive list of local brews, 30 unique cocktails, and over 100 whiskeys, The Pint & Cork is an industrial-styled gastropub that buzzes with energy every night. If you happen to give this bar a go, do try their house craft cocktails!

Fleetwood’s on Front Street - Yes, you read it correctly, that Fleetwood from Fleetwood Mac. Mick Fleetwood’s own bar is known for its scenic rooftop and downstairs bar that resembles a speakeasy. Their menu has a unique selection of cocktails inspired by the island of Maui itself, so don’t forget to try a Mai Tyler topped off with foam.

Milagros Food Company - Tequila is the main star of this bar. Milagros Food Company is well known for having the most diverse and vast tequila collection in all of Maui’s island. The best part? You get to build your own margarita if you’re feeling adventurous!

Fleetwood's on Front St, Maui Island.JPG

Fleetwood's on Front St, Maui Island by @ringside

Bars in Hawaii Island (The Big Island)

Huggo's On The Rocks - Take a deep breath and gaze over the sunset while you relax at this waterfront bar. You’ll be able to enjoy some live music on the cliffs of Kailua-Kona while you sip a Hawaiian cocktail during happy hour.

Beach Tree Bar & Lounge - This bar is one of the gems of the Four Seasons Resort Hualalai. If you’re looking for signature cocktails, some appetizers to keep the hunger at bay, and the Pacific Ocean just a few sandy steps away, look no further.

Lava Lava Beach Club - Picture a bar. Now a beach. What about a bar that’s actually on the beach? Take in the sea breeze while you dip your toes in the sand and enjoy a tropical drink. Oh, did we forget to mention there’s brunch available every Sunday?

Rays on the Bay - The name of this bar & restaurant is not in vain. You’ll have the opportunity to try the freshest seafood while feeling like you’re in an open-air aquarium. The family of Manta Rays that live in front of this bar will surely be a sight to remember.

Kona Brewing Co. - Ever heard of the “Liquid Aloha” beers? If so, meet the original brewery and pub for these popular brands! You can enjoy a guided tour of the brewery and take part in a taste-testing of the many microbrews available.

Woman sipping a drink at Lava Lava Beach Club, Big Island.JPG

 Lava Lava Beach Club, Big Island by www.wanderlustwithlisa.com

Maria Jordão
Lisbon, Portugal
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