4 Days in Oʻahu: An Indie Couple’s Guide

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Ashanty Cruz
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Ashanty Cruz

  • Beaches

  • Boutique Travel

  • Couples Travel

  • Arts & Culture

  • Off-the-Beaten-Path Travel

  • O‘ahu

  • Island

Advisor - 4 Days in Oʻahu: An Indie Couple’s Guide
Curator’s statement

I might be a little biased because I’m a local to the area, but O’ahu is truly special because of all the variety it has to offer. You can take in the city life one day and the up-country adventures the next--all in one trip. You have access to art, food, culture, nature, and more all on one island.

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Day 1: Explore Kaka'ako

Diamond Head (Le'ahi)

Beat the crowded spots and head for Kakaako. Grab a treat at Okayama Baker or a Taro Donut at Holy Grail. Have a picnic on the beach at Ala Moana Beach Park. Take a night boat tour at Kewalo Boat Harbor or head for dinner at Nori Bar. But also, make sure you stop by Fishcake for unique gifts for yourself—think local artists made stickers, ceramics, and prints.

Day 2: Take a surf lesson

If you’re looking for an authentic experience without a crowded lineup—I recommend going with Hawai’i Surf Guru Surf School. Uncle Kimo, the owner, taught me how to surf, and his lessons come with more than just surf guidance. He’s truly a wise man. He’s been surfing the Rockpiles break for over 40 years, so when you take a lesson you get to surf with his friends and family, too. If you’re looking for an authentic, knowledgeable surf lesson— this is it!

Day 3: Snorkel with turtles and swim with sharks

Take a one-hour drive to the famous North Shore. Walk through the beautiful, lush Kawela Bay and make sure to bring your snorkel and fins (whenever I come here I see so many turtles in the water). And the nice thing? There’s never a crowd, so you feel like you’re in your own little oasis. If you’re feeling adventurous, book a tour to swim with sharks (with or without a cage)! It will be something you will remember forever, and many people have raved about the experience.

Day 4: Get a tattoo on your final day

Women-owned Honolulu tattoo shop Greenhouse.hi is the spot to commemorate your trip with a fatigue-free flash tattoo or something personalized. It’s a fun way to wrap up your trip and share time with your mate (just make sure you’re not sun- burnt). I recommend reaching out a month in advance to save your spot.

Need to know

Always throw out the shaka if you accidentally cut someone off—it’s the polite thing to do.

Ashanty Cruz

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Ashanty Cruz

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