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Hawaii Begins in Oahu

Hawaii Begins in Oahu

The first time I went to Hawaii, I made a mistake. Well, many mistakes, but one major one: I used Oahu only as a crash pad and, after just a couple of days there, abandoned it for Maui.

Now, I realize that Maui has just been through a terrible time, but the reality is that many aspects of the island rubbed me the wrong way. Oahu, by contrast, left me wanting more. So when I returned to Hawaii a few weeks ago, I decided to spend my entire trip there.

While it’s true that you’ll enjoy your trip, no matter how many days in Oahu you decide to spend, I implore you: Stay here as long as you can—and longer than you think you need to.

Need help planning your trip to Hawaii? Hire me as your Travel Coach!

Oahu is More Than Just the Place Your Land

The topic of how many days in Oahu you should spend is extremely relevant—I should know. On my first trip, I arrived at my Waikiki hotel late in the evening; the next morning, I drove up to the North Shore, then back around the eastern coast of the island to return to the beach in time for a sunset catamaran. When I headed to the airport to fly to Maui my third morning, I remember looking down at Diamond Head and feeling sad I hadn’t scaled it.

While I hadn’t fallen in love with the island to such a great extent that I looked into long distance moving in Hawaii, I did know that I hadn’t done it justice. Diamond Head notwithstanding, I’d failed to get reservations at gorgeous Hanauma Bay; I’d passed the Dole Plantation on the way up north, but hadn’t managed to stop for a Dole Whip. I’d rushed through my trip (and wasted it as a result); as you’ll see below, I made up for it the second time around.

How to Make the Most of Your Time in Oahu

Start in Waikiki—but don’t end there


Waikiki isn’t what it used to be. At least that’s what my mom, who first visited in Hawaii in 1980, told me as we lounged on Waikiki Beach two Thursday mornings ago. The good news is that in spite of Waikiki’s urban problems—no parking; tons of homelessness—the beaches is still absolutely gorgeous, particularly with iconic Diamond Head rising above it.

Watch surfers at the North Shore


No matter how many days in Oahu, you owe it to yourself to drive up to the North Shore, ideally stopping en route at the Dole Plantation for some Dole Whip. There’s so much to do here, from the “shrimp trucks” along the main road in historical Haleiwa, to the surfers catching waves at Waimea Bay and Banzai Pipeline. You may also want to visit Waimea Falls, although I warn you: The entrance fee is excessive.

Don’t skip Oahu’s eastern edge


Many travelers go to Oahu’s North Shore, but many others skip the northeast. To get here, head across Oahu on the Pali Highway, stopping at Nu’uanu Pali Lookout en route. You can also pivot over to Byodo-in (a replica of the real temple in Uji, Japan) before heading east to Waimanalo Beach. From here, drive eastward until the road starts looping south and back west. In my opinion, this coastline is the most beautiful part of Oahu.

Make reservations for Diamond Head (and certain other places)


The bad news? The Haiku Stairs have long been closed (and have always been dangerous). The good news? There are other “special” places you can visit, regardless of how many days in Oahu you have. The first is Hanauma Bay, a protected beach for which reservations go on sale just two days in advance. The second is the Diamond Head hike, which you can book up to three days before travel.

TIP: As much as it pains me to say this, Pearl Harbor is not worth visiting. The US government has turned this hallowed graveyard into a scam, which cheapens the memory of everyone who died here. A true shame!

Leave time for rainbows (and magic)


One of the my biggest regrets from my first, too-quick to Oahu? I didn’t see any of Hawaii’s famous rainbows, which had been at the top of my mom’s list. So, when we returned, we purposefully visited places that are known for them, including the Tantalus Lookout, which might be my favorite viewpoint of Honolulu. Whether for prismatic colors or for other magic, having an extra day or two in Oahu leaves space for the intangible.

Where to Base Yourself in Oahu

I’ve stayed in Waikiki both times I’ve visited Oahu so far, though that was more due to my mom’s nostalgia than my own desire. She’d stayed there when she came back in 1980; her entire reason for coming to Hawaii was wanting to relive memories from that time. While I loved The Surfjack, the hotel where we stayed, Waikiki hotels are generally overpriced and old. Many clearly haven’t been renovated since the 1980s!

The next time I go back to Hawaii, I’ll probably stay up on the North Shore, whether in one of the super-cute towns like Haleiwa, or in a place that’s more rural, but with easy access to beaches like Waimea Bay and Banzai Pipeline. Or perhaps I’ll stay east toward Waimanalo Beach. Then, of course, there’s the question of how many days in Oahu I’ll stay then.


Other FAQ About Your Trip to Oahu

Is 5 days in Oahu enough?

In my opinion, five days is the perfect amount of time to spend in Oahu. This allows you to have a full day lounging in Waikiki, a day on the North Shore, a day exploring the island’s eastern reaches and two free days. You can use these to visit “reserved” destinations like Diamond Head and Hanauma Bay, or to hike trails in the island’s lush exterior.

Is 3 full days in Hawaii enough?

Three full days might be enough time to see Oahu, but it’s definitely not enough time in Hawaii writ-large. If you wish to visit the four main islands—Oahu, plus Maui, Kauai and the “Big Island”—you need a minimum of a week, and ideally 10-14 days. If you’re going to make the journey all the way to Hawaii, do yourself a favor and give yourself enough time for it.

Is Maui better than Oahu?

Maui was one of my life’s greatest travel disappointments. From eroded beaches on the west coast, to unfriendly locals along the Hana Highway, to infrastructure that is woefully inadequate for the number of tourists who visit the island, I can’t imagine myself ever returning to Maui. Oahu, on the other hand, is delightful and satisfying. So no, Maui is no better than Oahu—the opposite is true, in my opinion.


The Bottom Line

This post is less about how many days in Oahu you need, and more about how you should devote as much time to the island as you can. Many tourists write Oahu off—Hawaii’s main airport is here after all; you “have to” spend at least a night here, right? But the reality is that Oahu is in many ways Hawaii’s most satisfying island, and certainly the one whose treasures are mostly easily accessible. I recommend staying a minimum of 3 days in Oahu in order to full appreciate the magic the island has to offer. Another tip? Hire me as your Travel Coach if you want personalized assistance putting your Hawaii trip together.


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