Waikiki Sunset Cruise: BYOB Sail & Swim Trimaran Experience

4.94

(185 reviews)

What’s the experience like?

“You brought the pineapple beer, right?” That’s how our Waikiki sunset cruise started—me fumbling through my bag while the crew grinned and pointed out the “no glass” sign (which I’d missed). The Hokulani trimaran was way bigger than I expected, almost like a floating patio with netted seats where you could just sprawl out. There was this salty breeze mixing with sunscreen and something sweet from someone’s guava drink nearby. Our guide, Kaleo, kept saying we had the best seat in Waikiki for sunset—and honestly, he wasn’t wrong.

We sailed right past Diamond Head, which looked sharper and more dramatic from the water than it ever does from land. The Royal Hawaiian Hotel popped up all pink against the sky. I tried to take a photo but mostly ended up squinting into the wind and laughing at my friend’s hair blowing everywhere. The deck felt steady even when we picked up speed—someone said that’s because of the three hulls? I don’t know boats but it made sense at the time. There was this shaded spot they called “the nook,” where some folks just lounged and watched Magic Island drift by in slow motion.

When they dropped anchor off Waikiki Beach for swimming, I hesitated—then jumped anyway. The water was cooler than I thought but so clear you could see your toes wiggle. Coming back onboard with wet hair and sand stuck to my legs, I sat on one of those nets with a can in hand, watching the sun melt into orange over Honolulu. People were quiet for a bit then someone started humming along to a ukulele playlist from someone’s phone. It felt unplanned and perfect in that small way you remember later.