4 Days in Waikiki
I just got back from an incredible four-day trip to Waikiki on the island of Oahu with my youngest son, Jonah, and let me tell you — if you’re looking for the perfect blend of relaxation, adventure, and amazing food, Waikiki is where it’s at. Oh, and did I mention Jonah turned 18 while we were there? Nothing like a milestone birthday in paradise, right? Here’s the rundown of how we lived our best lives in Waikiki — from sport fishing and infinity pools to ukulele lessons and (probably too much) shaved ice.
Table of Contents
Where We Stayed: Sheraton Waikiki
We stayed at the Sheraton Waikiki, and honestly, I might have to move in permanently. The location? Perfection. Right on the beach, walking distance to everything. We only had to grab an Uber to and from the airport — which means more time for the important stuff, like mai tais and beach lounging. The rooms are comfy. Each room has a coffee maker with Hawaiian coffee and a tea kettle, a Japanese toilet, and a balcony.
The hotel itself is everything you’d expect from a top-tier Hawaiian resort. We kicked things off with a free ukulele lesson (because when in Hawaii…), then hot tubbed like pros and even learned to make a flower bracelet — which, by the way, is easier than it looks.
One of the highlights? Renting a private cabana at the adults-only infinity pool. Floating in that pool with ocean views and drink service? That’s what vacation dreams are made of.
The cabanas are available to guests as well as people that just want to visit for the day. You can book a cabana here.
Sports Fishing
Turning 18 is a big deal, so we decided to go big with a deep-sea fishing trip with Aloha Charters LLC — and it was epic. Our guide, Jerry, was fantastic — the kind of guy who knows all the best spots and makes you feel like you’ve been friends forever. Jonah reeled in a mahi mahi (cue the proud mom moment), and I somehow managed to catch a marlin. Still not sure how that happened, but I’m taking the win.
If you’ve never been sport fishing in Hawaii, put it on your list. There’s nothing like the rush of hooking a big one while surrounded by that deep blue Pacific water. And the look on Jonah’s face when he pulled in his catch? Priceless.
Where We Ate (Because Food is Half the Fun)
We didn’t just eat well — we ate like royalty. Waikiki is a food lover’s paradise, and we did our best to taste it all:
🍽️ Dinners
- Duke’s – A classic spot, right on the beach. Fish tacos and mai tais while the sun sets? Yes, please. Plus, if it’s your birthday you get a free dessert.
- Rumfire – Trendy with a killer ocean view. Their cocktails alone are worth the visit. Happy hours starts at 4 PM with some good drink deals. I had steak and Jonah had a hamburger. We had the Japanese fried chicken for an appetizer and it was insanely good.
- Tonkatsu Ginza Bairin – If you’re craving Japanese, this place nails it. The crispy pork cutlet was next-level.
- Wicked Maine Lobster – Because sometimes you just need a lobster roll (or two).
We also had dinner at Monkey Pod one night and I do not recommend it. That’s how we ended up at Wicked Maine Lobster in the food court next to our hotel.
🍦 Desserts
- Baskin Robbins – Not your typical Baskin Robbins — they have shaved ice! Highly recommend the tropical flavors. We had one on-site at our hotel so we took it back to our cabana.
- Island Vintage Shaved Ice – Hands down the best shaved ice we had. The difference between theirs and many others is that it is served with soft serve vanilla ice cream, popping boba, and mochi. Get the lilikoi and thank me later.
🍤 Lunches
- Giovanni Shrimp – The garlic shrimp? Legendary, and now you do not have to venture all the way to the North Shore just to get some. They have a small location in Waikiki.
- High Tea at the Veranda at Moana Surfrider – This was such a treat! Fancy little sandwiches, scones, and tea overlooking the beach — very posh, very delicious. You can upgrade your tea to add a burger or a mimosa flight.
🍳 Breakfasts
- Sunrise Shack – The açai bowls were refreshing and perfect for starting a beach day. There is very little seating here. It’s basically grab and go.
- Kai Market – All the breakfast classics, plus tropical fruits galore and excellent views. Jonah had the steak and eggs which must have been good because he demolished them. I had the vegan eggs benedict which were delicious. We also tried the Portuguese sausage since we’d never had any before.
Other Highlights
Between all the eating and fishing, we managed to soak up some good beach time. Waikiki Beach is exactly as beautiful as you’d expect — golden sand, turquoise water, and just enough waves to make things fun without scaring off the kids (or moms). We spent a lot of time walking along the beach and exploring the shops nearby. You could literally spend a whole day wandering around without ever getting bored.
Why Waikiki is the Perfect Spot
This trip had everything: a little adventure, a lot of relaxation, and some seriously good eats. The Sheraton Waikiki was the perfect home base, and the walkability made everything so easy. Jonah’s 18th birthday was one for the books — catching a mahi mahi, eating his weight in shrimp, and soaking up the Hawaiian sun.
If you’re planning a trip to Waikiki, take notes — sport fishing, infinity pools, and high tea might just be the winning combo you didn’t know you needed. Aloha! 🌺
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