Hawaii Trip #2-1: Background, Travel and Day One

Background and Planning

Diving in! This trip is our second to Hawaii as a family, and a repeat of a trip here last year. We usually take a trip each year for Meghann’s birthday week, with South Korea in 2022, Okoboji in 2021, and even managed a trip to Sedona during COVID in 2020. This time we’re here for seven nights, staying at Outrigger in Waikiki. 

While this trip series is titled “#2-1” (the first number implies how many times we’ve traveled to the location, and the second number is ordered post sequence from that trip), there isn’t a “#1” Hawaii series. Historically I’ve only written when on international trips, however last year’s Hawaii trip covered so many cool activities and neat photos that it felt like a disservice to not write! Memories and details beyond can be fleeting, so these posts serve as a way to share and remember, and will serve the same purpose for my daughters down the line.

Last year’s Hawaii trip included the Polynesian Cultural Center, Surf Lessons, spa day, a half-day trip to north shore, lots of good food, and even a chance run-in with Jason Momoa! It was also the first trip where we used ChatGPT to plan and build our itinerary, something we’ve continued doing since.

PHX to HNL

Fortunately I can keep this commentary relatively short! Phoenix to Hawaii is a direct flight that’s roughly five hours. Hawaii’s time zone is “HST”, three hours earlier than PST. Flight went relatively smooth, outside the family of 20 behind us which included a toddler with impressive lungs and stamina. Upon landing, we rented a vehicle (Wrangler four-door!) and headed to our hotel. After check-in, we requested a room change as our “partial ocean view” was pretty underwhelming, especially compared to the one we had last year. They were able to accommodate and we ended up in a much better spot!

First Night In

After getting settled in the room and relaxing a bit post-travel, we decided to head down to walk the beach. Outrigger has beach-front access, with rentable chair/umbrellas, surfboard/bodyboard rentals, and even “Faith’s Surf School” where you can take group or private surfing lessons. 

After exploring the beach, we headed down to dinner at the Hula Grill, which is on the 2nd floor of the hotel. We had a table overlooking the ocean as well as the outdoor patio at Duke’s (1st floor hotel restaurant) which had a live band. Notably they played “Pirate Looks at 40”, one of my favorite Jimmy Buffet songs that I don’t hear often outside my pool playlist. I had Mahi Mahi topped with crab and macadamia nuts, while Meghann had a very delicious steak. Just as delicious was the dessert – Sage and I shared their famous “Hula Pie” and Meghann and Vivienne had upside down pineapple cake. Yum!

We had aspirations to go walking after dinner, but between the travel day and huge dinner we decided heading back to the room seemed like the better option. With the long day – we turned in early to get some rest for the days ahead! 

Day One

After a good night’s rest, the first day started early. Today’s agenda – BEACH DAY! It’s our only totally unstructured day of the trip where we can ease into things. First thing, Meghann and I took turns getting in runs at the hotel gym. Pretty basic gym here – three older treadmills and some basic weight equipment. The treadmills had a 30-pin connector for your iPhone, which I’m sure would be great if you’re still using the 2011 iPhone 4S or earlier.

After the gym, we headed down to the beach to reserve some beach chairs and an umbrella for the day. The hotel has a beach hut which opens at 8am. We got there about 15 min early and were able to snag some chairs in the front row. After getting all set up, we went up to the second floor of the hotel for breakfast at Voyager 47. Access to Voyager 47 is included in our room rate which serves breakfast every day and appetizers/drinks in the evenings. The food is pretty basic standard fare “continental breakfast” plus fresh Hawaiian fruits. Best part is sitting on a beautiful terrace overlooking the ocean.

After breakfast – beach time! We got changed and headed down. We decided to kick things off with renting body boards for the girls. This was their first time trying it, and as expected, mixed results! Meghann and I each got in to help them get started, and they each managed to have some successful surfs in to shore. They hung in for about 45 minutes before deciding to move on to some swimming ahead of lunch. 

For lunch, we took a walk and ventured down to one of the other Outrigger properties, Outrigger Reef Waikiki Beach Resort. Meghann found a restaurant “Steak Shack” that served a delicious and healthy meal of grilled steak, salad and rice. Post-lunch was back to our beach spot. Apparently the 45 minutes taking photos and 20 minutes walking put my skin at its “sun saturation” point, so I hunkered down under the umbrella while the girls continued to swim. Around 3pm we all headed up to the room to clean-up and rest up before dinner.

We had dinner at “Aloha Melt Waikiki”, a small establishment that focused on grilled cheese – YUM. Pretty simple menu of six items. The girls all had the four-cheese grilled cheese, while I had the Aloha Spicy Patty Melt. We also ordered a bowl of their in-house tomato soup to share as dip. Food was delicious, worth a return visit at some point. 

On the way back, we found a “K-food” convenience store which was half stocked with things you’d find in Korea. We ended up getting a bottle of soju, and… bubble tape. The shopkeeper was entertained on checkout that we spoke some very basic Korean with him. 

Tomorrow we start the day with hiking Diamond Head at 10am, with the rest of the day open. Maybe find a new beach? More to come!