Oahu Road Trip Ultimate Itinerary & Guide, Hawaii (2024)

Hawaii is one of our all-time favourite destinations. It’s the perfect mix of island living with the attractions of a city.You have the option to relax, explore, shop, eat, drink and cruise the entire island in just a day.

There are many ways to get around Oahu. Guided tours, public buses or mopeds but we strongly, strongly suggest renting a Mustang convertible or a Jeep Wrangler for a self-guided, hair down, music-pumping road trip along the scenic Kalaniana’ole and Kamehameha highways.

If you prefer to be on a tour and have someone else drive, check out the Oahu Majestic Full-Day Circle Island Tour.

Oahu is small enough you can get around in one day, but large enoughto have plenty of things to see and do.It is possible to do all of thesesuggested stops in a day, but keep in mind it would involve jumping in and out of the car all day, without a lot of relaxing, so pick and choose based on your interests.

Below you can see an interactive map of the spots outlined below. We suggest drivinganti-clockwise to hug the coast.

Go at your own pace, stop when something beautiful pops up (there’s a lot!) and follow no set plan. Freedom at its finest.

Here are our recommended stops!

Waikiki

You’re bound to start your dayat this world-renowned beach. 80% of tourists are based in this area and it is where the most action/hotels/restaurants and of course, people are. It’s not for everyone but in our opinion, it’s still a very buzzing, beautiful place to spend at least a day, especially for sunset.

View Hotels in Honolulu.

A Day in Waikiki

Start the morning off with a long stroll along Waikiki Beach,starting at the lagoons in front of the Hilton Hawaiian Village and continuing down the beach towards the Honolulu Zoo (or vice versa). The earlier you go, the fewer people to navigate. Take a break halfway to relax on the golden sand, people watch (very fun & funny!) and then grab a surf or paddleboard from one of the rentals and head out to catch some waves.There are tonnes of people (mainly beginners) in the water so be careful.

Sit down for lunch at the Cheesecake Factory (the portions are out of this world huge, so get sharing or come starving) and don’t forget to try one of their outrageously delicious cheesecakes. Caramel Turtle flavour for the win. Stretch your bank account with the endless shopping or duck into the Honolulu Cookie Company for some free samples. As the sun starts to set, sip a co*cktailat the Ala Moana Hotel, the oldest hotel in Waikiki or atDukes, a staple tiki bar with live music. For dinner, head to Lulu’s for the best coconut shrimp & more live entertainment from 6:30 pm. Looking for something a little more upscale?Roys Waikikiwill do the trick with high-end Hawaiian fare.

Waikiki Sunset Boat Cruise

Who doesn’t love drinking in the sun on a boat? In Hawaii! Yes, please!

If you have more time, we’d recommend going out on one of the many boat tours leaving from Waikiki Beach. For 2 hours and only $40 USD or $45 during sunset. They give you unlimited booze (beer, spirits, soft drinks, water) combined with an awesome boat ride. If you’re lucky you can see whales and dolphins. You can’t miss the bright yellow boats docked right out the front of Dukes. They leave every couple of hours.

If you prefer certainty, book a sunset cruise!

Hike Diamond Head

Hiking Diamond Head is definitely a must do when visiting Oahu, especially first thing in the morning. In the early 1900’s, the military claimed Diamond Head as a site for code defence, creating the paths, tunnels and stairs that still today are part of the terrain. The 1.5-mile hike which takes anywhere from 1.5 2 hours can be tackled by almost anyone. I couldn’t help but sing “the ants go marching one by one hurrah hurrah” as we hiked up the windy, steep hill alongside the hoards of other tourists. See here for more of thebest Hikes in Oahu.

There areviewpoints the whole way up but the best, most incredible view lies at the very top after you’ve climbed up 74 stairs, followed by 99 extremely steep stairs, through a relatively dark tunnel. Bring water and avoid doing this in the middle of the day!

Gates are locked at 6:00 pm daily and the last entrance in is at 4:30 pm.$5.00per car or $1 per person for pedestrians.

Hanauma Bay

The first stop after Diamond Head will be Hanauma Baywhich issnorkel heaven on the southwest coast of Oahu.This bay is formed within a volcanic cone and has more than 400 species of Hawaiian marine life. You can choose to cool off here after you’ve hiked Diamond Head or just stop here for the view. Entrance to the park is $7.50 per person but for parking is only $1. If you leave within 15 minutes, they will give your $1 back ;). If you’re feeling extra energized before or after your snorkelling at Hanauma Bay you can hike Koko Crater Trail(shown below).We’ve never done it but we’ve heard it’s rather tough!

Please note Hanauma Bay is closed on Tuesdays!

The Lava Tube

This is one of Oahu’s “secrets”. Thanks to our local friends Mike and Lara, we were introduced to the Lava Tube. You can find this just past the Lanai Lookout (park in that car park). Take the road to the right and go over the barricade on the left side. It looks as though there’s nothing there but just keep going. Walk 10m down a small hill, most likely covered in rubbish, then turn to your left and you should find a small narrow hole leading right out to the ocean. Ssssh, it’s a secret, don’t tell anyone!

Sandy Beach Park

As soon as you turn the corner from the Lava Tube, it’ll be hard to keep your jaw off the floor of the car. The views were immediately stunning and on a clear day, you can see the neighbouring island of Moloka’i.

Not only can you enjoy the fine sand between your toes and the incredibly blue water at Sandy Beach Park, you can also grab a bite to eat at one of the food trucks parked in the car park. If you love Mexican, Leilani’s Island Tacosshould be your next stop.2 HUGE tacos full of flavour for only $10!

Be careful though, this beach is known to have dangerous shore breaksthat only locals dare to tackle.

Lanikai Beach

You know when someone says “take me to my happy place”? For me, that isLanikai Beach, one of, if not my favourite beach in Oahu.

The water is always perfect, it’s never too crowded (although it is becoming a little more popular than it was last time we visited) and it seems like a world away from it all. Bring yourself a ‘lilo’ aka pool float and enjoy the moment & sunshine. There’s little beach parking so you’ll have to drive the backstreets to find parking. If the weather is clear, take the short hike up to Pillbox Hike to overlook the beaches below.

Kailua Beach Park

1 mile on from Lanikai is Kailua Beach Park. A popular calm beach 2.5 miles long. Kailua has picnic tables, large grassy areas, showers and bathrooms and free parking making it a perfect place for a family day out. Stop by Kailua town, just 5 minutes from the beach to grab yourself some things for a picnic.

Tropical Farms

Who doesn’t love a free sample? Just when you’re starting to get peckish, stop into Tropical Farms. A macadamianut farm selling a gigantic variety of nuts and a whole lot of free samples! They also have free Kuna Coffee to try which Jacob greatly appreciated. It’s tough staying awake in Hawaii ;). Just be aware, ALL the tour buses come here so you will have to share those samples with a few others! You don’t need longer than 10-15 minutes in here, get in, get fed and get out 🙂

North Shore

North Shore = Blue Crush(the 2002 movie). At least that’s what I think about when the North Shore comes to mind but there’s plenty more to the North Shore than the waves of Pipeline.

Getting to the North Shore along theKamehameha requires driving along both the coast and the countryside of Oahu. You’ll pass by Kualoa Ranchwhere many movies have been filmed and continue along the roads surrounded by stunning mountain backdrops that make you feel you’re living inthe world of Jurassic Park. If you have more timeThe Polynesian Cultural Centre is a great place to experience a typicala Lūʻau– a typical Hawaiian feast but you’ll need more time for this.

Stop in for a co*cktail and/or lunch at Turtle Bay Resort,a secluded resort on the tip of Oahu. This resort is one of the few hotels in the North Shore and due to its remoteness, it can be very relaxing but also rather far away from anything else. If you’ve got a spare $400 a night, why not treat yourself to a night or two. Take us too! (But take note that helicopters fly over every 10minutes!)

Continuing on you’ll be spoilt for choice when it comes to beaches along the North Shore. For 5 mi/8km beginning at Sunset Beach, there is no shortage of places to stop.Banzai Pipeline is one of North Shore’s most famous beaches and is well known for its ridiculously large waves and surf competitions during the winter months. So impressive! During the rest of the year, the waves are at a “normal” level but the currents can be strong.

Furtheron past pipeline isShark’s Cove (opposite this beach is a small carpark with food trucks),Waimea Bay (rock jumping has become a popular activity) andLaniakea Beach also known as“Turtle Beach”where turtles make a regular appearance on the sand to lay eggs.It’s impossible to miss this as you’ll notice the cars all gathered around.

Haleiwa

Haleiwa is the place to spend the afternoon after a day at one of many surrounding North Shore beaches. This old historic town has a relaxed local ambience which is a far cry from Waikiki. There are a lot of surf shops, boutique stores, restaurants & art galleries. Grab a meal atHaleiwa Beach House or shrimp from the famousGiovani’s Shrimp Truck.

Next up?Shave Ice!No trip to Hawaii is complete without at least one shave ice.Matsumoto’s Shave Icefirst opened its doors in 1951 and since then has been serving exotically flavoured shave ice to people from all around the world. For something so simple, it tastes so delicious and highly refreshing. Frozen ice covered in sugary flavours. Mmm.

The thing that makes Shave Ice so different in Hawaii is the option to add ice cream on top? Like it isn’t cold enough already! I hate to say it, but this is definitely one of those essential stops and a great way to cool down.Warning: Don’t ever call it a snow cone! Those Hawaiian locals will have something to say about that ;).

Dole Plantation

As nighttime soon approaches it’s time to make your way through central Oahu down the Kamehameha HWY towards Waikiki but not without one last stop at the Dole Plantation. I mean, sure some may say this is a “tourist” trap but it was still worth the stop if anything just for the Dole Whip Icecream! Did you know… In 2008, Guinness World Records named Dole’s Pineapple Garden Maze the world’s largest maze made up of 14,000 colourful Hawaiian plants. Operating hours are 9:30 am – 5:30 pm.

Pearl Harbour

Photo credit: Wikipedia

The infamous Pearl Harbouris a place to remember, honour and understand the heroes of Pearl Harbour – the site of the WWII surprise attack by the Japanese. You can visit the Pearl Harbor Museums, the USS Arizona Memorial, USS Bowfin Submarine, USS Missouri Battleship, Pacific Aviation Museum and plenty more. It was a very moving experience and definitely worth the visit.

Top Pearl Harbour Tours

Now head back to Waikiki and tomorrow, maybe you could go surfing or scuba diving. See Expedia forhotels for scuba divers.

Top Tips

Don’t leave anything valuable in your car at any time.
Car rentals are reasonably priced (considering) but we found Alamo to have the cheapest car rentals of all the companies. We’ve used them on every occasion we’ve been in Hawaii, picking up & dropping off at the airport.
One-way drop off fees are pretty steep and begin at $50 USD. Try rent the car from the same place that you wish to drop it off (ie. the airport or in Waikiki).
Drive anti-clockwise to have the ocean always on the right side of you.
Don’t forget to use sunscreen when you’re driving. It’s a killer with the roof down.

Hawaii, this is not the first and it will definitelynot be the last time we see you! Mahalo!

Married Days Survived; 935