What does a minimalist (who likes oversized silhouettes) wear to Hawaii?
What we ate, where we went, and what I wore on Oahu
This trip was pretty much the two of us relaxing, beaching, sleeping, eating on repeat, and I wouldn’t have had it any other way. Usually an overplanner and an overthinker for trips out of town, this time, I wanted to let things happen as organically as possible. Blame the pregnancy hormones or how crazy my schedule’s been in the last month or so, but I really did not have it in me to plan out the details for this trip, even when my husband gave me weekly reminders. The only things I had was a list of places to visit/eat at written in my journal (thankfully I remembered to take a snapshot before leaving) and recommendations that our friends texted. After dropping off our Poppy to doggy daycare the evening before, we were on our way the following Thursday morning.
Day One
We arrived at Honolulu International Airport early afternoon, which meant I was already starving after spending six hours eating granola bars, cookies and nuts. One of the places a friend recommended was Hula Dog, a food truck restaurant located on Kapiolani Blvd. and a 15 minute walking distance from our hotel. We dropped off our luggage and headed over. I ordered a hot dog with Hawaiian bread, polish sausage, jalepeno sauce and Hawaiian mustard. My husband ordered the Hula Polish Dog (Hawaiian bun, Polish dog with Roasted Garlic lemon sauce, Mango Relish and Lilikoi Mustard). I devoured mine because of how hungry I was, and the sweetness of the Hawaiian bread was a good balance with the savory sausage and sauces. My husband enjoyed his too but he thought it had too much bread (which I didn’t complain about since I love carbs).
Afterwards we took a Lyft to Waiola Shave Ice. We both ordered the Waiola Rainbow (Strawberry, Vanilla, Banana) and relaxed on a bench in a shaded area behind the entrance of the convenience store.
We had dinner at Kalmuki Shokudo, where they serve dishes tapas style, which is exactly what I like in terms of portion size. My husband had the don, and we enjoyed the garlic butter scallops, grilled veggies and Okinawa sweet potato salad. My favorite was the salad for its creamy texture, sweet-savory taste and overall presentation.
We walked over to Cow Cow’s where I tried their famous yoghurt drink with purple rice (mango flavored), which was interesting but not something I would want to order again. It was definitely good for a one time experience.
What I wore
During the day, I styled my Simone Fan terry blazer with a Sunspel tee and James Perse drawstring pants with SeaVees rubber clogs. I accessorized with my Janessa Leone Waverly hat (which was incredibly essential for sun protection due to its wide brim and foldability).
For dinner, I changed into a cream colored pleated top. Every single outfit I wore were styled with my Janessa Leone Tanner straw bag, which has become my go-to tote for spring and summer.
Day Two
Usually I am a Type A planner for trips, but this time, all I had was a list of recommended places to eat (after scouring Reddit forums and Substack posts) and my friend’s list of places to visit. Whether it was the emotional fatigue from working nonstop or pregnancy brain, I just did not feel like planning, preferring to kind of go with the flow. Because this is our babymoon, I did not want to exhaust us to the point of feeling overly tired throughout the day, as I am known to do when planning outings.
For breakfast, we visited Sunny’s Local Grind. I found this place on Yelp as their brekkie burritos looked absolutely delicious, which is what I ended up ordering. My husband got the Loco Moco, of which I stole several bites (since I got pregnant, I have been loving the gravy on these).
By this time we decided to rent a car (a must in Hawaii, as it turned out), so we Lyfted to a hotel for pick up, only to realize that the hotel was right next to the Royal Hawaiian, which was minutes away from Waikiki Beach. We walked along the shore (it was so crowded!), and was able to rest for a few minutes on some beach chairs before getting kicked out by a family that reserved them (we have to pay to sit on them, of course). Despite the crowd, we definitely got a taste of Hawaii that we came to experience.
After getting our rental car (which wasn’t cleaned, but it wasn’t in bad shape. That’s another thing; definitely reserve a rental BEFORE arriving at your destination if you want to save time and money), we headed over to Leonard’s Bakery, famous for their malasadas (Portuguese fried pastries) and ordered a half dozen (I loved the original, the guava, and custard). We detoured to a local Safeway market to pick up some drinks and Maui-style chips to snack on between meals.
Once we got back to the hotel, we had some downtime, napped, and then visited the pool area, where we took a dip for about ten minutes and I was able to catch up on ACOTAR. That evening, there was a five minute firework show, which was short and sweet. Dinner was lowkey today: papaya for me and an egg salad sandwich for hubby purchased at the hotel souvenir/food store . It was still enjoyable because we had an incredibly funny interaction with the cashier, one that will stay with me for a long, long time.
What I Wore
A few days before my trip, I stopped by RLT to buy some basic tees and tanks, which are some of the softest basics I have ever worn. One of my favorites is the RLT Sydney tank. I also bought the soft baby tee in white and red (Sunburn), all in size small. Today I also wore my Eileen Fisher wide legged linen pant.
Day Three
I slept in a little longer than expected, mainly because I woke up with the worst lower back pain I felt in weeks. Figuring out the best way to sleep while in the third trimester of pregnancy definitely takes trial and error.
We walked about five minutes to the local McDonald’s, where we ordered a deluxe platter (white rice, spam, and Portuguese sausage) and dessert (Taro pie). I have to admit, the platter was pretty good, probably because I absolutely LOVE spam.
There is a well known sushi restaurant on the first floor of Prince Waikiki hotel (where we stayed at) called Katsumidori Sushi, a popular spot for their deluxe tuna platter. I cheated and had two small bites, which was all I needed to understand why it was highly recommended. I usually prefer salmon, but the tuna literally melts in your mouth and is flavorful.
My husband’s friend recommended that we try the coconut shrimp at House Without a Key located within the Halekulani Hotel. Sadly the coconut shrimp was no longer on the menu, so we ordered a pizza, fries, and their signature coconut cake (which we devoured within eight minutes). We did not make a reservation, but the outdoor seating area with live entertainment was a first come, first serve basis. We got very lucky and were seated second row from the very front of the stage, which also boasted a gorgeous view of the sunset and the ocean.
Afterwards we explored Luxury Row, stopped by the DFS to browse on the way to our rental car.
One other thing I was able to finally get started on with our baby registry (from what I researched, Babylist was the favorite platform amongst redditors).
What I wore
At the pool, I kept it simple and comfortable with my RLT soft baby tee in “sunburn,” and white linen Eileen Fisher pant.
For dinner I changed into a Jenni Kayne silk shirt and black drawstring pants.
Day Four
Another day, another McDonald’s breakfast (trust me, I am NOT complaining; the Hawaiian deluxe platter is the best and this has been the most invigorating, relaxing vacation we’ve experienced in YEARS).
We made it a point to stop by Musubi Cafe Iyasumi on our way to Kailua beach, where we met with my husband’s colleague and his family. Kailua beach is crescent shaped and located on the eastern side of Oahu, known for the beautiful scenery and calm waters.
As I am now in my third trimester, I wanted to avoid choppy waters and crowds as much as possible. We enjoyed a light lunch of spam musubis and fruit drinks we brought for the trip (my favorite is the tuna and mayo onigiri). The waters were incredibly refreshing once we dipped our heads in, and the waves were quite mild. It was a little overcast but still lovely.
For dinner we went to Ramen Ono-Ya close by our hotel where I ordered the shoyu ramen and a ramune drink.
We were finally able to find some Dole Whip soft serve at Aloha Whip for dessert and enjoyed a brief stroll along Luxury Row.
What I Wore
L*SPACE bikini (top and bottom)
Day Five
Despite the sunscreen I slathered on for Kailua, my shoulders, chest and back were still a bit sunburnt. But that did not stop us from finally making it to Waimanalo beach on day 5. Since the start of our trip, we heard so much about this beach (I even wrote it down as one of the places to visit before we arrived in Hawaii) and it is by far my favorite beach of all time.
The drive itself was smooth and scenic (about 25 minutes from our hotel), and we drove past the bluest waters we have ever seen (I was nearly in tears at one point).
I found Ono Steak and Shrimp on Yelp, famous for their fish tacos. I got the tuna tacos and my husband ordered the garlic shrimp. As a bonus, the girl who worked at the counter recommended the best place to leave our car. That’s the other thing that made this trip worthwhile; looking for a place to leave the car was the easiest experience ever.
One thing I would recommend when visiting Waimanalo Beach is try to go in the morning before the winds pick up. What I can’t get used to in California beaches was how cold the waters are; here, it was just the right temperature to wade in, neck deep.
On our way back to the hotel we detoured to Ululani’s for shave ice. After a shower and a nap, we ate dinner at 100 Sails, the restaurant in our hotel, and realized we had completely forgotten about visiting the local farmers’ market (the white pineapples will have to wait until next time we visit Hawaii).
After such a hearty meal, we decided to get more Dole whip, which did not disappoint.
What I Wore
RLT Soft baby tee in white
Eileen Fisher white linen pant
Day 6
Today was the last full day in Oahu, and also my birthday!
Ono Seafood was one of the places recommended to us by our friend, so we had to drop by. My husband likes poke and so do I, but I ordered the tako as it is fully cooked. It was a bit of a splurge for breakfast (around $50 including drinks), but it was worth the delicious food.
Skull-Face Books & Vinyl was open today, and as it is affiliated with The Last Bookstore, a visit was definitely in order.
I bought two books (Clarice Lispector’s Agua Viva and Artur Schopenhauer’s The World As Will and Idea) and left, but not before taking selfies and playing chess with my husband (in which he swiftly beat me of course). On our way back to the hotel we stopped by Daily Whisk Matcha and I ordered an iced hapa matcha latte (blend of hojicha and matcha).
We drove to Bellissima Hawaii Nails & Beauty (located on the third floor of the Waikiki tower at the Ala Moana Hotel) where we both indulged in mani/pedi treatments. The ladies were incredibly sweet and my manicurist did an incredible job with my cat eye nails.
We relaxed back in our hotel and I even napped for about 30 minutes. I woke up just before dinner at Chart House, a walking distance from our hotel.
I was incredibly jealous of my husband’s steak, but my salmon was good and so was the crab cake. I felt like we truly indulged (and deservedly so) on this trip which was was a nice treat for both of us.
After dinner, we made our final trip to Waikiki’s Luxury Row to browse some of the stores (one of which we spent considerable time in because I did end up receiving a birthday gift there).
Note: If you decide on a rental car (which is a must have), I would definitely park at the post office on Kalakaua Avenue that allows you to park using the ParkMobile app for a minimum of two hours. During rush house it can get incredibly congested and deeply frustrating to drive through, especially when there road closures.
What I Wore
James Perse men’s crewneck tee
Eileen Fisher white linen pant
Havaianas flip flops
Day 7
We had an afternoon flight to catch back to Long Beach, but I woke up early to check in on some work related emails.
We had a light lunch of spam musubi and onigiri (again from Musubi Cafe Iyasumi) then headed over to the airport to shop for some souvenirs.
Tips and Recommendations for visiting Oahu:
Get a rental car! Surprisingly, no one told us to do this. Ideally it is best to have one reserved at the airport when you arrive on the island as it saves money and time. And there’s a good chance it will have been cleaned by then.
Visit the local spots. There are so many small businesses that have great food, especially frequented by locals. Looking for and dining at these places were some of the best parts of our trip.
Break in your flip flops. I know this sounds silly. I bought a brand new pair of Havaianas for the trip and I ended up with painful blisters between my toes that didn’t go away for a few days.
Prepare for unexpected road closures and traffic. An easy 10 minute drive can become an hour long stretch, and you also have to look for parking. Also chances are you may have to pay wherever you leave your car.
This is just a personal preference, but try to visit the beaches in the morning. We wanted to avoid too many waves crashing into us as much as possible because of my pregnancy. Going in the morning just worked out for us because we still enjoyed a hearty meal at lunchtime, and by the time we got back to the hotel in the afternoon, we were able to rest.
I live on Oahu. If you just want to hang out in Waikiki a car isn’t necessary, but it’s a must if you want to explore. I’m glad you went to two of the best beaches on Oahu and that you enjoyed your trip!
Looks like a fantastic and delicious babymoon! Congratulations!