OAHU, Hawaii

associate.x
Mar 14, 2019
8 min read

Updated: Apr 26, 2023

Hawaii is not one, but a collection of islands about six hours east of the U.S. mainland. The most popular islands are Oahu, Maui, Kauai and Big Island of Hawai’i. To make the most of any trip to Hawaii, you will probably want to visit at least two of the islands.

From Australia, you will fly in to Honolulu on the island of Oahu and inevitably spend some time there. I remember Oahu for its golden beaches, imposing mountains, epic hikes and heart-stopping views. There is a lot to do and I recommend hiring a car or else you are limited to Waikiki. Other people love booking a resort in Waikiki and just unwinding by the pool and the beach. My entire itinerary could easily keep you busy for over a week, but if you have a short trip planned, you could definitely mix and match a fun itinerary over 4-5 days. I gathered these memories over two trips to Oahu, and there is still more to do.

1. HIKE THE CROUCHING LION TRAIL

52-204 Kamehameha Hwy, Kaneohe, HI 96744. Parking at Swanzy Beach Park.

I haven’t actually done this hike! We went to the wrong entrance and accidentally did the most dangerous hike in Hawaii (Pu'u Manamana). Don’t do that one. We passed a few too many gravestones on the trail commemorating those who had slipped off the unprotected cliffs. Apparently the Crouching Lion trail is a more PG trail next door offering similar but safer views. The trail begins between the "Do not pass" sign and a telephone pole on Kamehameha Hwy. The climb will be steep but should only take about 30 mins up and down. From the Crouching Lion, you have the same beautiful views of Kahana Bay as well as the view of the deadly ridge that we accidentally hiked.

2. WALK UP THE DIAMOND HEAD TRAIL FOR A VIEW OF WAIKIKI

Diamond Head State Monument, Honolulu

This is a relatively easy uphill paved walkway and stairs overlooking Waikiki and the ocean. Because even kids and non-hikers can complete this easily, it is usually crowded. There is easy access from Waikiki but an entrance fee of $5 per car and $1 per pedestrian is charged (cash only). We walked from Waikiki because we didn't want to pay for a bus (and the guy at the hostel really underestimated the walking distance) and that made it quite epic on a hot day, adding an hour uphill. After walking all the way up and down, you can reward yourself with a dip in that ocean at Waikiki Beach.

3. EXPLORE WAIKIKI

Waikiki is buzzing with people, street performers and activities by the beach. While Waikiki beach is crowded, it is still beautiful and gets great waves. There are many stands offering surf boards and surfing lessons. There are lots of nice restaurants and shopping. Some of our favourite places to eat were Marukame Udon (build your own udon) and Heavenly Island Lifestyle (organic twist on Hawaiian classics). The Cheesecake Factory will have an enormous wait so nominate someone to go and wait with a buzzer 30-60 minutes before you actually intend to eat. They have huge meals and so much cheesecake - we saved the leftovers for the budget plane ride home. I usually spend at least an hour shopping at Ross, which sells heavily discounted designer and branded items.

Heavenly Island Lifestyle: 342 Seaside Ave, Honolulu, HI 96815, USA

Marukame Udon: 2310 Kūhiō Ave #124, Honolulu

Cheesecake Factory: 2301 Kalakaua Ave, Honolulu

Ross: 333 Seaside Ave, Honolulu, HI 96815, USA

4. SINK YOUR TEETH INTO ONE OF TEDDY'S BIGGER BURGERS

134 Kapahulu Ave, Honolulu - and other locations around Hawaii.

Don’t forget that you’re in Amurrrica and fast food is always part of the true American experience. The west coast has In’N’Out, the east coast has Shake Shack... and Hawaii has Teddy’s Bigger Burgers. Teddy’s Bigger Burgers was birthed in Waikiki and scattered throughout Hawaii. I guess they are “bigger” because standard burgers in America are 1) burger bun, 2) burger patty and 3) pickles. Everything extra is “deluxe” as I found out when I disappointingly ordered a standard burger at Chick Fil-A. You might have to line up for your burger at Teddy’s in Waikiki but you’ll get a burger filled to the brim with toppings and everything is made to order. Oh and everything in America is bigger.

5. WATCH THE SUN RISE ON THE STAIRWAY TO HEAVEN

The views from this 3,922 step former-naval staircase are legendary, but the hike is not for everybody. It is by far the most physically-challenging hike I have ever done. I was sore for days in places that I didn’t even know I had muscles. Secondly, there is the small problem that you could face fines up to $1000 if you climb. There is a security guard at the entrance to the stairs who is likely to just remind you that you are trespassing as you pass and begin your hike. There is a back way that avoids confronting the guard, over a fence and through a bamboo forest, joining the stairs about 50 metres up. If you’re going for sunrise (this hike will be beautiful at any time of the day), all this will be done in the dark so you want to bring maps and torches. Just beware that the residents of Haiku hate being woken up by tourists before dawn. You will need to be careful of booby traps and be quiet enough to not attract attention from residents who will not hesitate to call the police on you, or at least yell at you like they did to us. What an adrenaline rush.

Once you get on the steps (more like a ladder), you’re in the clear and you begin a breathtaking 3-4 hour climb. There are some loose steps and railings, but it's generally safe - if you slip, you’re not going to fall off a cliff and die. You’ll be relieved when you realise that hundreds of tourists complete the climb every day. The views are phenomenal and it was my favourite thing we did in Hawaii. I trained on the 1000 steps in the months preceding this but in the end, only adrenaline is the only thing that physically got me through. I remember really appreciating my friends. I don't do this kind of stuff on my own, because I physically and psychologically can't. I have these incredible experiences because my friends include me in theirs.

6. HIKE TO THE LANIKAI PILLBOXES

301 Kaelepulu Dr, Kailua. Directly across from the Mid-Pacific Country Club.

A moderate, exposed walk up and over a mountain ridge with beautiful views of the one of the prettiest beach and coastlines on Oahu. Like most hikes in Hawaii, the rocky gravel trails can be a bit tricky but if you wear good shoes and bring some determination, you will be fine. The pillboxes are big concrete structures that are great to sit and look out from. This trail is about a 1.5 hour round trip.

7. SOAK UP RAYS AT LANIKAI BEACH

After hiking to the pillboxes, you can cool off at Lanikai Beach below. It is ranked as one of the most beautiful beaches in the world.

8. SURF IN THE NORTH SHORE

The big waves in Hawaii live in Oahu's North Shore, approximately 45 minutes drive from Waikiki. Surfing was invented in Hawaii and the North Shore is home to some of the world's premier surfing competitions. Check out the waves at Banzai Pipeline which is notorious for huge waves. You will find kms of beaches perfect for surfing, swimming, cliff-jumping and walks. The historic surf town Haleiwa, is also worth a visit for its surfie shops, art galleries and surfie culture.

ACAI BOWLS AT HALEIWA BOLS

66-030 Kamehameha Highway, Haleiwa

Instagram: @haleiwabowls

Even if you're not into surfing, you should stop by for an acai bowl for breakfast at Haleiwa Bowls. Perfect on a hot Hawaiian day, these instagram-worthy tropical smoothie bowls are packed with fruit, oatmeal and antioxidants. They seem to be considered a health food! For the less-health conscious, there is a delicious peanut butter option. All that good fruit surely cancels the peanut butter out! Unlike in Australia, Hawaiian acai bowls are made from real acai berries that are not available in Australia, which makes them superior and a great Hawaiian experience.

9. PIG OUT AT A NORTH SHORE SHRIMP SHACK

Shrimp trucks are parked along the coastal highways along the North Shore and are popular at lunch time. People gather round plastic tables and sometimes on the side of the street, getting down and dirty with these garlicky, buttery and delicious shrimp. Some classics include Giovanni's Shrimp Truck (66-472 Kamehameha Hwy, Haleiwa) and Romy's Kahuku Prawns & Shrimp Truck (66-472 Kamehameha Hwy, Haleiwa) on any road trip to the North Shore.

10. CHILL WITH THE LOCAL SEA TURTLES AT LANIAKEA BEACH

We tried spotted turtles at Laniakea Beach. We snorkelled too but they pop out of the water near the rocks, where it's difficult to swim. Sometimes they lay on the beach. The best time to go to see turtles is around midday. We brought our own snorkelling gear and flippers.

11. FEAST AT A LUAU

Paradise Cove: 92-1089 Alii Nui Drive, Kapolei

Polynesian Cultural Centre: 55-370 Kamehameha Hwy, Laie

Complete your Hawaiian cultural experience by booking in for one of these traditional Hawaiian feasts. At a Luau, you are treated to dancing and fire twirling while you are served a traditional Hawaiian buffet dinner of meat and fish. The #1 rated Luau is at Paradise Cove. We enjoyed the Luau at the Polynesian Cultural Centre which is a Polynesian theme park in Laie. I wish we had more time to learn about the Polynesian islands and watch the cultural presentations. But we got seated right near the stage at the Luau, and Zach and I got picked to participate in the Hawaiian dancing. Warning: This is not an authentic or traditional Hawaiian dance:

https://video.wixstatic.com/video/4bda41_e4d30cdd81ec4d3b8995c5fc85bea61d/480p/mp4/file.mp4

12. HIKE UP THE KOKO HEAD STAIRS

Until attempting the Koko Head Stairs, I wondered why hiking trails always brought you around the mountain and not straight up. This is a short but steep climb up straight up a mountain via an old rail track, but it's a great workout. The locals do it for fitness, like the Hawaiian 1000 steps. You are rewarded with panoramic views at the top but for me, but I just loved the physical challenge of the steps. You gain 300m in just over a kilometre of walking. You’ll feel proud of yourself once you get to the top.

13. TAKE AN ADVENTURE TOUR THROUGH KUALOA RANCH

49-560 Kamehameha Hwy, Kaneohe

Kualoa Ranch is the privately-owned, the real life set of Jurassic Park. The ranch offers a variety of ways to explore the beauty of the ranch including drive-your-own open air UTV, single-rider ATV (quad bike) tours, horseback and jeep tours. We did the ATV tour. Unfortunately, we didn't have great weather but you can still recognise the scenery and riding is still fun. Except if you fall off, you get banned from riding for the rest of the trip and I got stuck on a small hill and was hanging on for dear life, determined not to get kicked off the tour. Tours often sell out so you should book in advance at https://www.kualoa.com/toursactivities/ It might be fun to watch Jurassic Park and Jumanji (the latest remake) before you come.

14. LUNCH OR DINNER AT SEVEN BROTHERS "AT THE MILL"

Aussies seem to love the juicy handmade burgers at Seven Brothers in North Oahu. Maybe it reminds us a little bit of home. The vibe on a warm night at this outdoor restaurant is relaxed, like every holiday should be, and we kept making the trip back.

55-565 Kamehameha Hwy, Kahuku

15. VISIT DISNEY AULANI RESORT

We treated ourselves to some extra magic by staying two nights at Disney Aulani resort. The resort is situated in West Oahu, well away from Waikiki so it is not an ideal location for visiting Waikiki or doing any of the above activities. However, there is a literal schedule of activities that will keep you busy over a day or two at Disney Aulani, including a small water park, your own private beach, Disney character experiences, beach yoga and fitness classes, Disney movie nights, theme park shopping and live entertainment. The snacks are also on point - how awesome is dole whip (pineapple soft serve) from Little Ophi's and Mickey shave ice (traditional Hawaiian dessert) from Papalua Shave Ice! Disney Aulani is expensive, but to a hardcore Disney fan, you can't put a price on magical memories.

92-1185 Ali'inui Dr, Kapolei