Aloha, O’ahu!

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In September 2018 I traveled to Hawaii for my brother’s wedding. Before his wedding in Kailua-Kona (on Hawaii, the Big Island), I took a few days to go see O’ahu. I particularly wanted to see Pearl Harbor and Diamond Head.

I arrived in Honolulu just before noon, and was immediately struck by the size of the city. I knew Honolulu was big, and was the state capital, but I was prepared for an island feel, not a city feel. Though the island is really not that big, there are so many people that it takes quite some time to drive from one place to another.

near Fort DeRussy

I started my visit by stopping at my cousin’s (Todd) and freshening up, then took a Lyft down to the Waikiki area. It was….busy. Crowded. Full of name-brand shops and restaurants. Not what I was expecting, or wanting to see really. But I was starving, so I ate there (lucky I found a place that was more local). Then I walked over to Ala Moana to meet my cousin. Ala Moana is a massive shopping center, and the 7th largest mall in America. It was an easy place for us to meet, but it was overwhelming and we soon left!

We headed home to change and then Todd took me to the Manoa Falls Trail. This was absolutely incredible. Just a few moments in we came to an opening and I gasped. I felt like I was in Jurassic Park! From there on out, every day I was waiting for a massive T-Rex to pop out from somewhere and chase me. The hike was relatively easy; it does get rocky and uneven, so it’s good to be prepared for that with proper shoes and a walking stick if you need it. But overall, a manageable hike that ends at a beautiful water fall (Note: There is a parking lot nearby that costs $5, but we parked on the road leading up to the lot, in a residential area, and walked from there. It was free and gave us a warm up to the hike). The hike is really not far from the center of Honolulu and worth a visit. It’s a great way to start the day or decompress at the end of a long day!

hoping a dino doesn’t come eat me…

We ended the day by watching the sunset at Tantulus lookout. The drive up to the lookout was beautiful and near the lookout is plenty of park space for picnics and such.

looking towards the airport and Pearl Harbor
looking towards Diamond Head

The next day, I headed to Diamond Head with one of my best friend’s sister-in-law (small world, right?). This hike was a bit more difficult. There are some areas where it’s a bit steep and quite a few steps to climb. The worst of it is just near the end where you have to climb 99 or so steep steps, with no place to stop. But overall, I think it only took us about 30 minutes to get up, with quite a few spots to catch our breath. It’s absolutely worth it. The views from the top are incredible. You can see Waikiki, Pearl Harbor, the airport, and the south side of the island. Take plenty of water and sunscreen-I definitely showed up to my brother’s wedding with a sunburn from this hike (thankfully about half of the wedding guests also had various burns or cuts from hikes and snorkeling in our pre-wedding adventures, including the bride and groom!)

My hike guides, Jamie and Lucas!
Hey there, Honolulu!

Like Manoa, there is a fee to park at the base of the trail. We again parked further away near a park and walked up. This was a longer walk (about 10 minutes or so), but then we only had to pay $1 per person rather than the $5 per car, and again, got a warm-up to the hike. And the best part, besides the view? There’s a truck at the base selling smoothies and shaved ice-my favorite!! You can’t beat the views from Diamond Head, so I highly recommend this hike.

literally glistening from sweat

That night Todd took me on a beautiful drive to the east side of the island, to Lanikai Beach. The sand was soft and white, and the water was various shades of blue I’d never seen. We just sat there looking out at the water (or playing in it!); I didn’t want to ever leave! Check out my short video below to hear the beautiful ocean waves and see the view. This is a must-see in O’ahu! We went to the Lanikai Brewing Company in Kailua for a drink (I had a yummy guava cider), and then Kono’s for dinner. The kalua pig is a specialty in Hawai’i and is amazing. I loved it every place I had it!

standing in the warm, crystal clear water
Mokulua Islands

After my tour of Pearl Harbor (read about that here!), I met up with Todd who was flying out to CA for the weekend, so he lent me his car for the rest of my trip! At his suggestion, I drove up to Haleiwa, on the north side of O’ahu. Haleiwa is an adorable town, with lots of little shops, and some amazing shaved iced from Matsumoto.

a few shops in Haleiwa

After walking around and enjoying my yummy treat, I headed a bit further up the road to Sunset Beach. Unfortunately, I left exactly at the wrong time; there was a major accident and it took me over an hour to make what should have been a 20-minute drive. But I’m so glad I didn’t turn around. Sunset Beach was gorgeous-more white sand and crystal clear waters! I got a parking spot right near an entrance to the beach and found a bit of shade under a beautiful old palm tree. For the next few hours, I frolicked in the ocean, slept, and read. It was a perfect afternoon! I stayed to watch the sunset, but it was behind the clouds. It was still a beautiful afternoon and evening.

happiness is a good book and the ocean
the lovely 100+ year palm in my view for the afternoon

I drove back to Haleiwa for dinner (just a note, everything nearby closes early!) There were only two places open; I chose Uncle Bo’s and ordered a fan favorite, the Boca Rota. It is garlic cheesy-bread, prime-rib strips, sautéed mushrooms, and mozzarella cheese and some creamy sauce. Basically, one of the most amazing things I’ve ever eaten. Thankfully it was a huge serving and I could eat some the next day for breakfast!

Boca Rota. Yum.

The next afternoon I was headed off to the big island for my brother’s wedding, but in the morning I had time to kill. So I headed back to Tantulus Lookout for awesome views of O’ahu. I spent the morning reading and eating the rest of my Boca Rota. It was a great start to the day and a great end to my O’ahu visit. A quick trip, but worth it considering all I saw in just a matter of 3 days!

not a bad view for breakfast!
Aloha, O’ahu!


  1. Dianne Sullivan Reply

    Thanks, Kendra, for the beautiful tour of Oahu. Though we have been there once before, you’ve showed us some amazing places & sights that we somehow missed on our visit.
    Now we have some new places & things to see if we ever get to make another trip there!
    I so enjoy following your travels on your blog – flamingoagogo😄

    • Kendra Reply

      I’m so glad you enjoy reading about my adventures! And I’m glad I can add places to your bucket list 😉

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