Your Two-Day Itinerary to Oahu, Hawaii (following advice from a local)

If you’re visiting Hawaii, chances are that you’ll be arriving on Oahu. While we do strongly recommend that you explore at least one other island in the region (we prefer active vacations so chose the Big Island!), Oahu can be severely underrated as a destination in and of itself. We suggest you spend at least two full days exploring the island. Below is a two-day itinerary covering the must-see spots: we got our advice and itinerary from a local!

Note that a car is pretty much essential to explore the Hawaiian islands, and Oahu is no exception. Use our Car Rental 101 to find the cheapest deals for your getaway!

Day One

Diamond Head Hike

After a good breakfast at Sweet E’s Café in Honolulu (we loved this place!), head out for Diamond Head. This is pretty much a staple when you get to Oahu. Is it crowded touristy? Yes. You can visit in March or the Fall to avoid the heat (definitely a problem during this hike!) and a majority of the crowds but you should definitely still do this hike for the views. We suggest you hike this first, to get the crowded aspect of your itinerary out of your way!

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View from the top of the trail, Diamond Head

We visited Hawaii in early March, when the weather was mild but still warm to swim in the ocean, and there were very few tourists (we had entire beaches to ourselves!)

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The Diamond Head Trail
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The Diamond Head Trail viewpoints
Diamond head from above

H3 Highway

We cannot stress how important it is to drive this highway. The views are jaw-dropping. We’ve never seen anything like it! Remember to never park your car by the highway though (and hike away), for fear of your car being broken into.

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I mean…
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Pictures don’t really do it justice
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Come on!

Kaniakapupu Ruins

Used as a holiday home for King Kaniakapupu, these ruins are stunning. They are closed off to the public due to tourists littering and disrespecting the ruins, but the conscious hiker can get there. The only directions we can give you are that it’s off the H3 highway…

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The Kaniakapupu ruins

…and a little further on from the walking path that leads you off to the ruins, you can follow a disused pipeline that’ll lead you to a beautiful waterfall!

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Nu’uanu Pali Lookout

Off the H3 highway, visit this lookout for sunrise for stunning views over Oahu. You usually only pay for parking over the summer/peak tourist season.

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Nuʻuanu Pali Lookout

Waimanalo Bay, Beach, and Kailua Beach

You came to Hawaii for the beaches right?! You really can’t go wrong with beach hopping on Oahu but we recommend Waimanalo Bay & Beach and Kailua Beach Park for a less touristy and crowded experience than Lanikai and Waikiki beaches.

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Lanikai Beach

You’ve probably seen pictures of this beach before! Definitely worth a visit: try paddle boarding if you’re not a surfer in Hawaii!

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Lanikai beach

Byodo-In Temple

Need a break for culture from the beaches? Drive to Byodo-In Temple either early in the morning or in the evening (around 4pm) to explore the Japanese influence on Hawaiian culture. This is a stunning temple surrounded by beautiful greenery.

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Byodo-In Temple

Waikiki Beach

Our personal opinion is never to stay in Waikiki in Oahu – there are so many more beautiful places to stay in rather than this city hub on Oahu. Waikiki beach though is worth a visit for the sunset and some poke after.

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Waikiki beach for sunset

Day Two: The North Shore


The North Shore is our favorite area on Oahu and we absolutely recommend staying in Kaawa. You can easily drive from Kaawa to Waimea Valley and Haleiwa in a day, and the beaches and solitude around Kaawa (and the scenic stops) are unprecedented. We absolutely recommend Jana’s Airbnb for an INCREDIBLE experience if you’re looking for a place to stay (link coming soon, message us directly if you’re going soon!)

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Beaches by Kaawa

Laei Point

After lounging around the Kaawa beaches, take a drive to Laei Point.

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Haleiwa, Waimea Valley

Grab a bit from Ted’s Bakery and the Shrimp Trucks along the way, and drive to Haleiwa and Waimea Valley for the sunset!

One of the best meals I had in Hawaii. Top tip: Get the shrimp with rice to go, and have it at the beach!
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Sunset beach

Sunset Beach

Alternatively, you can stick to the ever-famous Sunset Beach. The highlight for us is that sea turtles often come ashore at the beach right after sunset beach if you’re driving south to north. You’ll see a few travelers milling about off the main road, and a small parking lot to your left. It’s definitely worth a stop!

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The way to be!

Top Tip: Try the poke! Even if you’re not a fan of seafood (or sushi – it’s really not for us!) poke can be delicious. Our favorite was actually buying different preparations of poke from the supermarket – they even beat out the dishes we had at restaurants!

If you have more time:

Pearl Harbour

Pearl Harbor is worth a visit but be warned: it requires a full day to explore, even if you’re quick adventurers like us! There are timed shuttles to battleships etc., that take time, so if you’re looking for a two-hour trip, this is not for you. If you’d prefer to just check out the exhibits without the battleships however, a quick trip is possible.

On a personal note: Please don’t litter during your vacation. We saw ridiculous amounts of trash off the highway etc. in Hawaii, and we shocked at how people can disrespect such a lush environment. Be a conscious traveler!

Planning a visit to Hawaii? You can’t miss out on the Big Island!

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Happy travels!

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