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Why Oahu Should Always Be Your First Hawaii Vacation

Hawaii Insider Guides Beaches and Islands
by Matthew Meltzer Dec 27, 2019

To say Hawaii is an anomaly among American states is an understatement. While it’s beautiful, wild, and magically calming, it’s also completely different than anywhere else in the country, feeling more like a far-flung island kingdom than our 50th state. This difference is a huge part of why Hawaii is such a special place to visit. But there’s a huge variety between islands, and you may not always find the infrastructure and amenities you’re accustomed to.

That’s not to say anywhere filled with warm Pacific breezes is ever stressful. That’s just to say if you’ve never been before, Oahu is the best place to start. You’ll find all the deep green nature, wild animals, and sandy beaches of your Hawaiian fantasies. But find it all close enough to a shopping mall if you’re in desperate need of air conditioning. (Hawaii is all about the “trade winds” and not so big on AC.) Here’s why Oahu offers the most complete package of all the islands in Hawaii, and why it should absolutely be your first Hawaiian destination.

The island is full of urban charms and low-key beach towns.

Waikiki Beach

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As the most populous island in Hawaii, Oahu is the cosmopolitan center of the state. And if you’re into big city amenities like shopping, cocktail bars, breweries, and international restaurants, Honolulu is where you’ll find it. Make sure to spend some time in Chinatown and visit Pig and the Lady, a Vietnamese spot on King Street with one of the best restaurant cocktail menus in America. Or wander around the arts district and hit Honolulu Beerworks, which feels about as close to hipster-industrial as you’re getting on the islands.

But an hour away you can hide in small, ramshackle beach towns that feel nothing close to Honolulu. The best way to see them is to just drive; take a car or a motorcycle and roll along the coastal highways, past farms, shacks, and beach bars that feel like a true, off-the-grid escape. If you’re looking for an endpoint, Haleiwa is probably the best known Oahu beach town, a small strip of surf shops and shaved ice stands that’s become a global destination for surfers. Kahuku on the northeastern shore sits between Laie and Turtle Bay and is famous for its abundance of fresh shrimp trucks. Or there’s Waianae on the west coast, a popular jumping-off point for water tours.

But comfortable accommodations are easy to find.

Turtle Bay Resort

Photo: Turtle Bay Resort/Facebook

Touring through far-flung islands can often mean staying in accommodations that skew a little…rustic. Especially in Hawaii’s other islands, where often your options are $700-a-night luxury resorts or tiny, local hotels. But in Oahu you don’t have to stay at the Grand Hawaiian or another mega-property on Waikiki. You can also find little boutique hotels like the Renew and the Surfjack Hotel and Swim Club, rehabbed ‘60s spots that have found new life with modern touches.

Ditto on the North Shore, which might feel completely removed but is also home to the epic Turtle Bay Resort, which you may recognize as Jason Segel’s ill-fated vacation spot in Forgetting Sarah Marshall. The multi-wing property sits on its own peninsula with large rooms and sweeping views, boasting gourmet restaurants and even a little nightlife at Surfer: The Bar. It’s not exactly a local scene, but does offer a comfortable respite along the rural North Shore.

You’ll find postcard beaches beyond Waikiki.

Lanikai Beach

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The golden sands of Waikiki, set under the watchful shadow of Diamond Head, are just about the most iconic vision of Hawaii you can find. That’s probably why Waikiki is also the most crowded beach, and while it’s a beautiful stretch of shoreline it’s not exactly secluded. The North Shore probably has the best variety of beaches without throngs of people, but if you aren’t up for that long of a drive you can find some great ones not horribly far from Honolulu.

Lanikai Beach might not feel completely remote, but it does offer calm waters and a couple of islands just offshore that double as bird sanctuaries. For swimming, it’s the best beach on the island, since the offshore reefs keep the waves at bay. If you’re looking for something a little more isolated, take the drive to Kahana Bay Beach Park. You won’t find any facilities or restaurants here, but you will find green and gold mountains tumbling right into the surf, and on many days not a lot of people.

Oahu is still a tropical jungle paradise perfect for hiking.

Kahana Bay

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Hawaii’s lone interstate highways don’t look much like the interstates you know. Rather than billboards and franchises along your drive, you’ll find vast canyons surrounded by rugged palms, massive ferns, and dripping banyan trees. And in less than half an hour after leaving the towers of Honolulu you’re transported back into the wild islands of centuries past.

Hidden in those mountains are trails that take you deep into the tropical rainforest. The easiest among them are along the Honolulu Mauka Trail System, a series of wide trails that are well maintained and popular with families. The Manoa Falls Trail is a nice, 1.6-mile round-trip to a 100-foot waterfall that isn’t terribly challenging. If you want to get deeper into the thick of it though, hit the Puu Manamana Trail, which takes you along a jagged mountain ridge. Or the Lanipo and Waianae Kaala trails, which bring you through the jungle to panoramic mountaintops.

You can dive by healthy reefs just minutes from downtown.


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Visiting a major city and scuba diving generally don’t go together; even in Miami you’ll typically need to drive an hour and a half to the Florida Keys. Not the case in Honolulu, where you’ll find wrecks and reefs less than 10 minutes by boat from Kewalo Basin Harbor downtown. Outfits like Banzai Divers can take you to the YO-257, an old navy ship that sits down 120 feet, or its shallower sister ship San Pedro, a swim-through-filled hospital vessel that’s become popular among sea turtles. There’s even an old Corsair plane that crashed into the ocean you can dive, too.

More impressive than the wrecks, Honolulu also sits right next to a massive coral reef. Its impressive preservation means you can get spectacular reef diving in as well, without having to endure a long, choppy boat ride — and get back from a morning dive with most of your day left to explore.

You’ll recognize Oahu from movies too.

ATVs in a row on unpaved road

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One of the great things about Oahu is that it combines true Hawaiian nature with straight tourism kitsch. At no place is this on greater display than the Kualoa Nature Private Reserve. It’s a stunning piece of property where you can take UTVs through lush valleys with straight shot views to the ocean. And drive to the tops of mountains to look down on the forest reserves and state parks around you.

You can also drive by a seven-foot-tall primate rib cage used in Kong: Skull Island, then pose next to a life-sized statue of Mighty Joe Young and a sign welcoming people to Jurassic Park. This is because in addition to being a perfect showcase for Oahu foliage, Kualoa’s also been used as a filming locale for dozens of movies. In case you don’t recognize the sites right away, the reserve is dotted with signs telling you which films were shot where, so you can recreate those scenes during your tour. It’s a fun, Insta-friendly way to immerse yourself in the island’s wilder side, but still unabashedly touristy.

Swimming with all your favorite animals is easy.

Swiming with sea life

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Another big Hawaiian draw is the opportunity to jump in the bathwater-warm ocean with animals you don’t typically get to see. Tours like Wild Side Specialty Tours operate off the west side of the island and can take you right into pods of dolphins swimming by green mountains. While in the water, you’ll likely also see sea turtles and possibly even false killer whales, a rare species of dolphin that’s often mistaken for orcas.

But far-and-away the coolest experience you can have here is swimming with sharks, which live in abundance off the shore of Haleiwa. People mistakenly think the reef and Galapagos sharks who live here are dangerous, but in fact they have about as much interest in biting you as you do in biting them. You’ll learn all about these sleek ocean dwellers on your boat ride with One Ocean Diving, who’ll give you an education in sharks and a new appreciation for their conservation before literally dropping you right on top of schools of them. It’s not even a little bit scary, but one of those things you can talk about when you get home and sound a lot more badass.

You’ll get the best of the islands, without having to get too far outside your comfort zone.

Sunrise from Hanauma Bay on Oahu, Hawaii

Photo: Shane Myers Photography/Shutterstock

Not that Hawaii is even a little bit intimidating, but it is the most foreign-feeling place one can go inside the United States, so figuring out how to navigate the islands can be a little overwhelming. On Oahu, everything you come to Hawaii for is within an hour’s drive of a major airport, and you can get the aloha spirit while still feeling close to home. With tropical nature, big-city amenities, and beaches literally surrounding you, it hits all the Hawaiian high notes. And if the Pacific breezes aren’t enough for you, you’re never too far from AC.

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