Waikiki Sunset Sail: Catamaran Drinks & Diamond Head Views

Summary

Waikiki sunset cruise with drinks music and Diamond Head views

You’ll set sail right off Waikiki Beach on a bright catamaran, sipping cocktails or juice while Diamond Head comes into view across the water. With music playing and locals sharing stories, you’ll watch sunset colors shift over Oahu’s south shore before gliding back toward city lights—maybe even spotting that rare green flash if you’re lucky.

What’s the experience like?

I almost missed the boat—literally. My sandal strap snapped right as I hit the sand at Waikiki Beach, so I hobbled over to the Ke Kai catamaran feeling like a lopsided tourist. The crew didn’t even blink, just grinned and waved me aboard with that easygoing way people have here. There was this faint smell of salt and sunscreen in the air, and someone’s laughter carried over the water. It felt like everyone was in on some secret about how good evenings can be in Oahu.

The catamaran itself is huge—bright yellow and purple, which sounds loud but somehow fits against the gold-pink sky. We drifted out from Mamala Bay while our guide (I think his name was Kaleo?) pointed out where Diamond Head starts to rise up behind Waikiki. He told us a story about its old volcanic crater—he made it sound like it’s watching over the city or something. I grabbed a mai tai (they pour them strong) and leaned back against the rail. The ocean breeze actually felt cool for once after a sticky afternoon; my hair got that salty tangle I never manage to brush out later.

Music played—some island stuff mixed with old pop—and people started talking more as we got farther from shore. At one point, someone asked if we’d see the “green flash” at sunset; Kaleo just shrugged and said you never know, but to keep your eyes open. I tried to catch it but mostly ended up squinting into the sun, half-laughing at myself. There was this moment when everything went quiet except for waves slapping under us and a kid nearby pointing at Diamond Head with sticky fingers from pineapple juice.

I didn’t expect to feel so relaxed with strangers all around me, honestly. Maybe it was the drinks or maybe just being out there with Honolulu lighting up behind us and nothing urgent to do for 90 minutes. Even now I still think about that view—the last bit of sun catching on the crater’s edge—and how nobody seemed in a rush to head back in.

Step-by-step itinerary

Day 1 — Sunset sail from Waikiki Beach

• Board Ke Kai catamaran at Waikiki Beach
• Sail along Oahu's South Shore
• Enjoy views of Waikiki Beach
• View Diamond Head State Monument
• Watch Hawaiian sunset with drinks

Top questions

How long is the Waikiki Beach sunset sail?

The sunset sail lasts approximately 90 minutes.

Does the tour include drinks?

Yes, complimentary alcoholic and non-alcoholic drinks are included for guests.

Where does the catamaran depart from?

The Ke Kai catamaran departs directly off Waikiki Beach in Mamala Bay.

Will we see Diamond Head during the cruise?

Yes, you'll have constant views of Diamond Head State Monument from the water.

Is there music on board during the sail?

Yes, there is music played throughout the cruise for guests to enjoy.

Are children allowed on this sunset sail?

Yes, infants and small children are welcome; they can ride in a pram or stroller.

Are service animals permitted?

Yes, service animals are allowed on board.

Is public transportation available nearby?

Yes, public transportation options are available close to Waikiki Beach.

What’s included

Your evening includes sailing directly off Waikiki Beach aboard a colorful catamaran with complimentary Coronas, mai tais, rum or vodka cocktails (for adults 21+), plus soft drinks and tropical juices for everyone. The friendly local crew shares stories along Oahu’s south shore as you take in Diamond Head views before returning under city lights.