A Day Sailing the Waikiki Coast
Last Updated on January 28, 2025 by Boatsetter Team
We had just left Ala Wai Harbor, sailing on the Ke Ānuenue, when Captain Sam yelled, “Whale! Breach!!”
Out on the horizon, a giant splash. “Tail!!” Captain Sam shouts, gleefully. “This is our first whale sighting of the season,” he exclaimed. The engine roared, and the catamaran picked up speed as we went to get a closer look of the whale. We were on a mission.
A giant black tail flipped out of the water. “Tail again!” Sam yelled out. “I think the whale likes someone on the boat,” the deck hand Charlie says. It was like he was waving at us. My five year old, West, snuggles into me tightly, keeping one eye on the water. 
Eager for a closer look, we propel faster and faster, our eyes darting back and forth, scanning the horizon for another sighting. “Calm water in the waves are the footprint of the whale,” Captain Sam tells us. The loud motor stops at the sight of them, and we halt in the middle of water. We stare out at the ocean blue with our phones out, hoping for a sighting. The waves lap and ripple and radiate the bluest blue. The sun, settling into the afternoon, warms us with its golden glow. The water lulls me into hugging the West tighter. Even the kids are still, without the tranquilizer of the iPad. I put my phone down. It’s so quiet I can smell the salt water.
It’s hard to believe we were just in Waikiki, maybe the most famous district in Hawaii. A tropical Las Vegas, jam-packed with Hawaiian-themed trinkets, $25/hr parking lots, and $30 over-sugared umbrella drinks in a coconut shell– it’s a barrage on your senses. Even the ‘io, the Hawaiian Hawk that people believed were royalty/gods themselves, can be viewed in his cage at the Waikiki zoo for $21 a head.
Man made Waikiki – he brought in the sand, built the parking lots, and put up the towers. And then he commoditized it. The history of commercializing paradise goes deep; anyone wanting to experience authentic Hawaiian-anything is instead served a packaged caricature of the island culture. Walking around Waikiki you can’t help but wonder, is this even Hawaii?
What is Hawaii, and where can we find it?
There was none such noise in the middle of the ocean, just 10 minutes out from the shore of Waikiki Beach, where Diamond Head looked so very different. Looking out into the great beyond you can’t help but think you’re in your Moana era—connected to a legacy of wayfarers and voyagers. They say there is some science to wayfinding, following the stars and the signs from the ocean, but everyone has their own way of doing it—their own special relationship to the water. And what it really comes down to, is a deep connection—a oneness—with the sea.
A deep connection — a oneness — with the sea.
We see water splashing out of a blowhole in the distance and suddenly the catamaran is on the move again. “What does breach mean anyway?” I finally ask the captain. “It’s when 30 tons of whale leaps its entire body out of the ocean. It’s their way of flirting with a mate, or even just showing off.” Ah, so the whale is flexing. I’m into it.
“Breach!” Captain Sam says. And there it is. Our own Free Willy moment, off in the distance, a gray humpback whale showing off his belly in all his whaley-glory before diving back into water. Of course we have no content to prove it, only a collective core memory forever etched for the eight of us on the boat.
“Let’s see it again!” the deckhand Charlie yelled out.
We never get another sighting but for the rest of the sail we are swelled with awe and wonder. We jump in the water and we dance on the nets. We soak in the beauty and the majesty. Everything nature is capable of.
The world so vast and mysterious. And us, out on the water. Still searching.
A boymom, wife, author, creative director, and the owner of Please Come Again ice cream in Kailua. She’s been living in Oahu for three years. Jo went out on a 2005 Power Catamaran with a Captain. Explore this boat.
