
A view of Waikiki from Diamond Head Trail
My first time on O’ahu was over Labor Day weekend in 2021, when Covid restrictions had lifted and all you needed to get in was proof that you were vaxxed and not a total idiot. Since I was dying to get out of town and had always wanted to see Hawaii – plus two of my friends were staying in Waikiki (the popular district in Honolulu, Hawaii’s capital) – I booked a cheap round trip from LAX and squealed with joy!
After two and a half sun-soaked (and gloriously sunburned) days on O’ahu with a rental car and a 12th floor hotel room at the Beachcomber, it’s possible I may have shed tears on my way to the airport to fly back home… and also on the plane.
Here are eight of my best tips for the perfect day in Waikiki, whether it’s your first time there or not!
1. Diamond Head Crater Trailhead

The most photographed feature on O’ahu is definitely Le’ahi (AKA Diamond Head), an ancient volcanic tuff cone with an iconic circular shape. It’s ridiculously close to the center of Waikiki, and there’s a popular hike there with breathtaking 360 views called the Diamond Head Crater Trailhead. This is a must-do if you’re hydrated and takes about 40 minutes up and down. Don’t count on parking, though – it may be best to Uber! And please don’t fall down the stairs. Get a transfer to and from with entry fee included
2. Manoa Falls Trail

Manoa Falls Trail is my personal favorite spot on the island (so far), probably because the rainforest is such a departure from the environments I know. The smells, the sounds, the flowing water, the lush dreamscapes, the sweat dripping from your brow! It’s an easy 30-minute hike about 20 minutes from Waikiki, with the slightest incline that ends at a classic Hawaiian waterfall. Parking at the entrance is cheap! Bring bug spray or accept your fate of itching. Kick up your Manoa Falls visit with an E-bike tour to the falls
Joke break: Why did the waterfall have a hard time in school?
It was always “falling” behind!
3. Lanikai Beach & Lanikai Pillbox Trail
Waikiki Beach is iconic and must be seen, but Lanikai Beach has a special secluded beauty! It takes a drive over the hill to the Kailua area and parking ain’t easy, but one must see the electric blue water and volcanic landforms. The nearby Lanikai Pillbox Trail hike is a little bit challenging – maybe don’t go if you’re hungover and susceptible to vertigo (oops) – but the view from the top is unbelievable.
4. Hanauma Bay Nature Preserve

Visiting Hanauma Bay requires a reservation because of its protected status as a Marine Life Conservation District, but if you can be respectful of this sacred Hawaiian site and its delicate coral reef – which is only for your eyes and illegal to touch – it’s incredible to snorkel here or lay out at the beach for an afternoon. Hanauma Bay is home to 450 varieties of stunning tropical fish! Find some of the world’s most amazing snorkeling here
5. Pineapple Dole Whip & shave ice
It might be a bit cliché, but these iconic Hawaiian treats are the most refreshing things you could possibly taste during or after a hot day in the sun. You can’t go wrong by searching your map for Dole Whip or shave ice in your area. If you’re on the main strip, try Island Vintage Shave Ice at the Royal Hawaiian! My favorite flavor is guava… and I dream of it all the time. I often wake up screaming in terror because I want it so badly.
Joke break: What do you call sushi in a tuxedo?
So-fish-tecated!
6. Poke, sushi, & seafood
Hawaii is known for its incredible poke, the dish of diced raw fish served in sauce or salad. I could have salmon sushi every single day and never get tired of it (I’m serious and it’s a problem) but I’d never tasted such fresh and delicious tuna until I had poke in Hawaii. Try Furusato Sushi for its convenient closeness to Waikiki Beach and its house poke bowl! There are also amazing restaurants on the main strip that have all kinds of seafood specials to try, and you can’t go wrong. I had my 33rd birthday dinner at Tanaka of Tokyo, a hibachi style seafood and steak restaurant. Check out Newdie Mags Hokey Poke recipe and dance.
7. Paddleboarding at the Hilton lagoon
The lagoon by the Hilton Hawaiian Village resort in Waikiki is a great spot for paddleboarding beginners to try their hands at staying afloat. (It’s open to everyone.) Paddle board rentals by the lagoon are easy to get – and if you’re a nervous wreck like me, you can always hang around to observe how it’s done before sliding into the water! Again, use caution if hungover.
8. Waikiki gay bars