Honolulu Sunset Sail: Waikiki & Diamond Head Drinks Cruise

Summary

Waikiki sunset colors, Diamond Head views and free-flowing drinks

You’ll board a lively catamaran at Kewalo Harbor for a sunset sail along Honolulu’s south shore, with Diamond Head always in sight. Enjoy unlimited drinks (beer, cocktails, juices) as you laugh with crew and watch Waikiki glow under shifting skies. Expect real moments: ocean spray on your face, music drifting across the deck, and an atmosphere that feels more like a celebration than a tour.

What’s the experience like?

Somewhere between the slap of waves on the hull and that first cold sip of passion orange juice (okay, I went for a Mai Tai after), I realized how different Honolulu looks from out on the water. We’d barely left Kewalo Harbor when our guide — big grin, sun-bleached hair — pointed out Diamond Head’s outline against a sky that was already starting to melt into pinks. The boat was this bright yellow catamaran, impossible to miss, and honestly felt like someone’s backyard party but with way better scenery.

The music was loud enough to drown out my awkward attempts at small talk, which I appreciated. People danced or just leaned over the railings watching Waikiki’s hotels start to light up. There was a salty tang in the air that stuck to my skin, and every now and then a spray of water would catch us by surprise — I heard someone yelp behind me and then everyone laughed. The crew kept refilling drinks (beer for my friend, something rum-heavy for me), and at some point one of them tried to teach us how to say “cheers” in Hawaiian. I definitely butchered it; Li just shook his head.

I guess what surprised me most was how quickly 90 minutes slipped by. Maybe it was the way the sun dropped behind Diamond Head or just that feeling you get when you’re surrounded by strangers who suddenly feel like friends. There wasn’t any pressure to do anything except enjoy it — no speeches or forced fun, just good music, free drinks, and Oahu’s south shore rolling past. I still think about that last bit of golden light hitting the water before we turned back toward Kewalo Basin. It didn’t feel like a tour at all — more like being let in on something locals actually look forward to.

Step-by-step itinerary

Day 1 — Sunset sail from Kewalo Harbor

• Board catamaran at Kewalo Harbor
• Sail south shore from Kaka'ako to Waikiki
• Enjoy views of Diamond Head
• Drink complimentary beverages onboard
• Experience music and crew entertainment
• Return to harbor after 90-minute sail

Top questions

Where does the Honolulu sunset sail depart from?

The sunset sail departs from Kewalo Basin Harbor, not Waikiki Beach.

Are drinks included on this sunset cruise?

Yes, all drinks are complimentary for guests aged 21+ with valid ID.

How long is the sunset sail from Kewalo Harbor?

The cruise lasts approximately 90 minutes along Oahu's south shore.

What landmarks will I see during the tour?

You’ll have views of Waikiki and Diamond Head throughout the sail.

Is this tour suitable for children?

It’s advised parents reconsider bringing young children due to party atmosphere onboard.

What kind of boat is used for this Honolulu sunset cruise?

The tour uses an iconic large yellow catamaran with decades of experience sailing Oahu waters.

Are non-alcoholic beverages available?

Yes, options include Coke, Diet Coke, 7-up, ginger ale, water, passion orange juice, and pineapple juice.

Is hotel pickup included?

No hotel pickup is included; guests must make their own way to Kewalo Basin Harbor.

What’s included

Your evening includes a 90-minute catamaran sail from Kewalo Harbor along Waikiki’s coast with endless views of Diamond Head. All guests can enjoy unlimited Pacifico or Modelo beer plus cocktails made with rum, vodka, gin or whiskey (for those 21+), as well as sodas and tropical juices served by a friendly local crew before returning to port just after sunset.