Oahu, Hawaii

September 2017


  • Lanikai Pillbox Hike
  • Renting a convertible and taking a scenic drive to North Beach
  • Stand up paddle boarding

Based on my trip, here is a quick list of my itinerary and places to hit. All places and things I highly recommend.

  • Stand up paddle boarding at Ala Moana Beach
  • Drive to North Beach
  • Lanikai Pillbox Hike
  • Ala Moana Mall
  • Tonkatsu Tamafuji: quite possibly the best tonkatsu outside of Japan?!
  • Shopping around Waikiki: this area of Honolulu is like one giant mall that has high-end stores that cater to Japanese tourists. It’s unavoidable, but still fun to walk around.
  • Farmer’s Market at Kapiolani Park (near Diamond Head)
Waikiki Beach

Hawaii… again?

If you had asked me last year to take a trip to Hawaii, I would’ve said no thanks, because I’ve been there four times and mostly know what it’s all about. I definitely enjoy what Hawaii has to offer, but I prefer new adventures.

Waikiki Beach, steps from Outrigger Hotel

But in July, August, and most of September I couldn’t travel anywhere, mostly because I was committed to a very big client and was just too busy and needed to stay close to the Bay.

This put a damper on my goal to travel somewhere every single month, so in the summer months, I explored some awesome hikes in the Bay Area instead. (More to come on my epic hikes!)

Not traveling for almost three months made me itchy to get out, so I booked a relaxing trip to Oahu. I used a mix of my points on my Chase Sapphire Reserve for hotels (Outrigger and Marriott). The plane ticket from San Francisco to Honolulu was only $350. Hell yes.

View from Sky Rooftop in Waikiki.

Hawaii is very touristy (Japanese tourists, anyone?), and as many touristy places go, is expensive. I avoided the pricier restaurants and mostly snacked on healthy-ish snacks that I bought from the supermarket near the Ala Moana Center.

I did a lot of hikes, hung out by the pool and beach, and drove to North Beach for a day. These activities weren’t very expensive.

View from my room in the Outrigger.

Paddle boarding at Ala Moana Beach

Must. Not. Fall.

Paddle boarding delivery: You can call places to bring you a board, beach chairs, a large beach umbrella and a cooler filled with ice for $99. I went to Ala Moana Beach for the first paddle boarding trip, since it was my first time and the waves are minimal there. It was so much fun! I only fell once.

I made it my mission to follow around a sea turtle I spotted.

Gentle, floating discs of the ocean.

I also paddle boarded on Waikiki Beach for $25 an hour. After paddling out, I realized it was too windy to stand, and I started getting sea sick. I mostly just sat on my board and tried to enjoy the sun and wind, but eventually turned in my board early.

Lanikai Pillbox Hike

View from the peak of Pill Hill.

This hike was no joke. I highly recommend this hike over Diamond Head or even Moana Falls. From the entrance, there are ropes because it’s THAT steep.

Brief selfie, before rushing back down the hill.

It’s a rocky entrance, but managed to complete it in 40 minutes, mostly because I parked in a “No Parking after 10am” zone. I was highly motivated to not get a parking ticket.

Diamond Head, skip this

Look carefully at the hill, do you see the line of people walking? Like a line of worker ants…

Imagine a slow-moving, crowded line at the airport TSA, then imagine everyone is shuffling up an incline — welcome to Diamond Head!

I’d skip it unless you can get there before 8am. Any later than that, it’s too crowded and hot. There’s almost no shade on the hike, and we walked uphill in a line, because it was so crowded.

View from the peak of Diamond Head.

My “what the hell are they thinking” moment: I actually saw runners on the hike. Runners yelling, “On your right!” to a bunch of Japanese tourists is a lost cause.

Kapiolani Park

After the hike, I strolled through the Saturday Farmer’s Market at Kapiolani Park. Hawaiians know what’s up. They engineered two of my favorite fruits into one. Yes, there’s such a thing as an apple banana fruit.

I bought a veggie burger and ate it on the grass.

The Saturday farmer’s market at Kapiolani Park, right down the street from Diamond Head.

Moana Falls Hike

Gargantuan trees of Moana Falls.

This hike is also touristy, it’s slightly better than Diamond Head because the trails are wider and the hike takes you through horticulture that has Jurassic Park written all over it.

Sweaty and sticky. Done with the hike though!

Again, I’d only recommend it if you’re going to get up early and beat the crowd. It’s fairly short (about an hour to the waterfall and back), but if it’s muddy from the rain, the trails can get slippery and a bit dangerous.

You see Tarzan anywhere?

Rent a car and drive to North Shore

The beaches are much quieter, north of Waikiki. This is Kaikaka Bay Beach Park, Haleiwa.

It’s nice to get out of the touristy parts of Waikiki Honolulu, so I decided to rent a cobalt blue convertible Mustang (can’t get more touristy than that). I stopped by a number of beaches along the way and enjoyed the sunshine. The beaches were surprisingly empty, but the waves were intimidating.

The sleepy, surfer towns around North Shore was a good change in scenery when you’re constantly around the hustle and bustle of tourists.

Public transportation

Taking the bus is really easy in Waikiki. You only need ~ $2.50 to get around anywhere, and I took the bus to and from the Honolulu Airport for less than $5.

There are also free shuttles that take you to various areas (i.e. Diamond Head). All you have to do is show your hotel room key. I kept my room key from the Outrigger because the shuttle didn’t accept the Marriott!

A bright Waikiki sunrise.

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