Waikiki Beach Day: From Morning to Margaritas
Date: 8 October 2025
Location: Waikiki, O’ahu, HI
The day in Waikiki started off just right with a delicious, filling breakfast that set the tone for a day of exploring. With energy up, we decided to take a walk toward one of Oahu’s most iconic landmarks, Diamond Head.
Last time I visited, hiking up to the summit was a spontaneous decision (and free). Unfortunately, things have changed since 2022 and you now need a reservation (which we didn’t have) and payment to hike to the top!
While disappointed, we made the most of it. The chance to walk into the Diamond Head crater visitor centre, was a new experience in itself.
Wandering through the neighbourhood outside of the typical Waikiki strip provided insight and a more local feel for island life; slower paced, and full of character. And as always framed by that incredible tropical backdrop.
After the 8km walk (!) an iced coffee was non-negotiable and we hit the jackpot at Aloha Cafe Pineapple. Hands down, the best one we’ve had so far (and we’ve had a few!). Smooth, cold, and perfectly balanced. Not too sweet, not too bitter. Exactly what we needed.
The afternoon was spent the way one should whilst in Waikiki: at Kuhio Beach swimming, lounging around, and soaking up the sun. The ocean was warm and inviting, the breeze perfect. Waikiki never disappoints when it comes to beach vibes.
Then came 3 PM and happy hour o’clock. It ended up being a bit of a bar crawl, starting at Maui Brewing Co. (great atmosphere and solid beers), popping into Shore Fyre (chill vibes, fun cocktails), and heading up to Sky Waikiki for some stunning views and even better drinks.
The night was complete with dinner and margaritas at OMG Mexican. A lively spot with big, fresh flavours (and even bigger portions).
All in all, it was a day that reminded us why Waikiki is such a beloved destination: even when things don’t quite go to plan.
What’s your favourite beach to swim at in Waikiki? What are your “go to” places for happy hour?
By Sarah 