Waikiki Sunset Sail: Oahu Catamaran Cruise with Cocktails

Summary

Golden hour sailing Waikiki coast past Diamond Head with cocktails

You’ll board a barefoot catamaran in Waikiki with local crew, sip your first cocktail as you sail past Diamond Head at sunset, and maybe spot humpback whales if it’s winter. Expect golden light on the city skyline, easy laughter with fellow travelers, and a real taste of Oahu’s laid-back evenings.

What’s the experience like?

The first thing I noticed was the way everyone went quiet when we left the dock — just for a second, you know? The city noise faded and there was this salty breeze that made my hair stick to my cheeks. Our captain, Keoni, grinned and told us to kick off our shoes (barefoot sail is a thing here) before we even stepped onto the Moana catamaran. I didn’t expect to feel that soft deck under my feet — kind of grounding, actually. Waikiki Beach looked almost fake from out on the water, all those hotels suddenly glowing in the late sun.

I grabbed a mai tai (first round’s on them) and leaned against the rail. There was music playing — not too loud — and someone behind me tried to say “mahalo” but tripped over it; their friend laughed so hard they almost spilled their drink. Keoni pointed out Diamond Head as we sailed past, its slopes catching this weird purple light I’d never seen before. He told us stories about growing up surfing right below it. I could smell sunscreen and pineapple juice mixing with ocean air.

At some point, a couple of kids spotted what they swore were whales (it’s humpback season from November to May), and everyone crowded one side of the boat for a better look. I didn’t see any tails but honestly, just being out there with strangers who felt like friends for two hours — that was enough for me. The sun dipped behind the city and everything turned gold-pink for maybe five minutes. I still think about that color sometimes when I’m stuck in traffic back home.

Step-by-step itinerary

Day 1 — Sunset sail along Waikiki Coast

• Check in by 4:45 p.m.
• Board Moana Catamaran
• Sail along Waikiki Coast
• Pass Diamond Head point
• Enjoy complimentary cocktail
• Watch Oahu sunset views
• Cruise ends at 7:00 p.m.

Top questions

What time does the Waikiki sunset sail depart?

The cruise boards at 4:45 p.m., gate closes at 4:55 p.m., and departs at 5:00 p.m.

Is a drink included on the Waikiki sunset catamaran cruise?

Your first round from the premium bar is complimentary; additional drinks are $8 each.

Do you have to remove your shoes before boarding?

Yes, it’s a barefoot sail—shoes are collected before boarding.

Is whale watching possible during this tour?

Yes, humpback whales can be seen from November to May along Oahu’s coast.

How long does the Waikiki sunset cruise last?

The cruise lasts approximately two hours, from 5:00 p.m. to 7:00 p.m.

Are restrooms available onboard?

Yes, there is a restroom on board the Moana catamaran.

Where does the cruise go?

You’ll sail along Waikiki Beach and out past Diamond Head on Oahu’s south shore.

Is transportation or parking included?

No transportation or parking is included; paid parking is limited nearby and rideshares are recommended.

What’s included

Your evening includes boarding the Moana catamaran at Waikiki Beach with experienced local crew, sailing barefoot along Oahu’s coast past Diamond Head while enjoying your first complimentary cocktail from the premium bar—plus access to restrooms onboard before returning after sunset.