5 Days in Oahu, Hawaii

Last September 2018 my cousin, Christine, my friend, Richiel, and I flew to Hawaii for the very first time. It was a short but one for the books trip!

DAY 1 – Flight to Honolulu

I left Halifax at 3:30 in the morning to catch my 5:30 flight to Toronto. And from there, I met my cousin at the airport to catch our flight to Los Angeles and then to Honolulu. We had a 4-hour layover in L.A., so we booked an Uber to go to the nearest In-N-Out burger (what else) from the airport. After another 5-hour flight, we finally arrived in Honolulu around 5 in the afternoon. Our aunt, my mom’s cousin, picked us up from the airport and was our host for this trip.

It was an early shut eye for all of us as we were tired from that day-long travel.


DAY 2 – Diamond Head Hike, Waikiki Beach

We woke up early, borrowed our aunt’s van and drove our way to the Diamond Head trail hike. It was only a 30-minute drive from our aunt’s place but due to Hawaii traffic it took us almost an hour to get there. We arrived around 8:30 am and it was already packed with tourists. It was an easy one mile hike and has one of the most rewarding views when you reach the top.

Hiking is about an hour and a half round-trip. We stayed a bit longer at the top for photos and climbed restricted fences to get these shots (don’t do it if you’re not willing to take some risks). Lastly, don’t forget to bring water for hydration. Though this hike is considered easy, it involved some stairs. Parking was $5 and cash only.


After our first Oahu hike, we checked-in early at Hyatt Regency Waikiki Beach Resort & Spa hotel. And then we headed to Duke’s Waikiki for brunch. My cousin booked a private surfing lesson in Waikiki beach, while my friend and I opted to chill at the beach.


We then got ready for our dinner at the Prince Waikiki Hotel. I highly recommend coming here for some all-you-can-eat seafood treat!

Dinner at Prince Waikiki with my aunt, godfather, Richiel and Christine.

DAY 3 – Drive to North Shore, Chief’s Luau

We woke up extra early on our 3rd day in Oahu due to jet lag. We spotted some sunrise surfers at the beach already so we thought about doing it too.

sunrise in Waikiki Beach

It was my first time to surf ever in my life so paying 100 bucks for a private lesson for an hour was a no-brainer. 

I never thought surfing was this fun! Definitely doing it again!

After our sunrise surf, we checked out from the hotel and headed straight to North Shore. It was just an hour drive from Waikiki. Our first stop was the picturesque town of Haleiwa. We first went to Haleiwa Bowls, famous for its açai bowls, and then to Turtle Beach to spot some turtles swimming at the shore.

We got hungry and headed back to town where you would spot an area of food trucks. Giovanni’s shrimps was our go-to place and it didn’t disappoint. After indulging ourselves with garlicky shrimps, my cousin and friend headed to Skydive; of course, I chose to stay and walk around the town than jumping off a plane. No regrets!

I had the best time strolling this small town. I did some shopping and also had the famous Matsumoto’s shaved ice, another North Shore favorite.

After our North Shore trip, we went straight to Chief’s Luau. For first time visitors like us, we can’t miss to watch a luau performance over dinner.

DAY 4 – Crouching Lion Hike, Ka’a’awa Beach, Kualoa Ranch

This was probably my favorite part of the trip. We woke up early to head to the not-so-famous hike that I carefully researched about. Authorities had officially closed the trail due to its dangerous cliffs and accidents. We honestly didn’t expect how steep this hike was that we almost ditched it. There was no official entrance to the trail and ended up hiking the wrong one. But when we finally figured out the right way, we were rewarded with the best views of the Hawaii mountains and the blue pristine beach.


After our hike we headed down to an empty Ka’a’awa Beach Park.

We drove to the nearby Kualoa ranch for lunch and then left to check the Hoomaluhia Botanical Garden. Sadly, visitors were no longer allowed to take photos on this insta-famous spot. I highly recommend doing a quick drive around the garden. Entrance is free and you get to see the mountains up-close too.

We became tourists for a good hour and really enjoyed the Kualoa Ranch movie tour. We hopped in a bus that toured us around the ranch where famous movies such as 50 First Dates, Jurassic Park and Jumanji got filmed. I suggest doing the last tour of the day as the best time to do the tour.


DAY 5 – Hanauma Bay, Makapu’u Lighthouse, Lanikai Pillbox and Lanikai Beach

On our last full day, we drove the eastern part of Oahu. We first stopped at the Hanauma Bay, a famous snorkelling spot. Unfortunately, we didn’t have the time to do it.

We then went to Makapu’u Lighthouse and then straight to the town of Kailua.

The town is known for its world-renowned Lanikai Beach. But before heading to the beach, we did the Lanikai Pillbox hike. It was an easy hike but my aunt, who we brought to hike with us, didn’t agree at all. This hike was a bit crowded due to its popularity but still a good one for beginners. Parking was a struggle too so I think it would be better to come here early in the day.

Lanikai Beach lived up to the expectation! It has the finest and whitest sand and bluest ocean waters. Lanikai in Hawaiian means “heavenly ocean” and this translation was so fitting.

My aunt insisted that we couldn’t leave Oahu if we didn’t visit Romy’s Kahuku Prawns Shrimp Hut. Another famous shrimp truck located in Kamehameha Hwy, Kahuku. The line wasn’t that long but we still waited for more than an hour but it was honestly worth the wait. Way better than Giovanni’s!

We had the best time in Hawaii and we can’t wait to go back already! Being here made me realized why do I even live in Canada? The weather was perfect, the food was great, and there were lots of things to do around the island. Also, we have a ton of relatives there! We still have lots of places we weren’t able to go; so, we’re leaving it on our next visit. Hint: Stairway to Heaven

Disclaimer: All opinions and views on this post are my own. Copyright all pictures by Kathleen of I Am Miss Adventures.

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Hi! My name is Kathleen and I’m the “Miss” behind this blog. I am a 30-year-old wanderer and story teller based in Toronto, Canada. I work in healthcare for a living and try to enjoy the outdoors during my free time.

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