Waikiki Sunset Sail: Open Bar Catamaran Cruise & Friday 21+

Summary

Waikiki sunset cruise with open bar and barefoot boarding

You’ll feel Waikiki’s pulse as you board barefoot for a sunset catamaran sail with unlimited drinks and friendly faces all around. Sip local cocktails while city lights flicker behind Diamond Head and laughter drifts across the deck. With open bar included and easy beach boarding, it’s more fun than formal — just bring your sense of adventure.

What’s the experience like?

I’ll be honest, I almost bailed last minute because crowds aren’t usually my thing — but something about Waikiki at sunset just pulls you in. We met right on the sand, toes sinking into that warm grainy stuff, and the Holokai crew was already laughing with a few regulars. You board barefoot, which felt weirdly freeing (and also slightly awkward when I realized my socks didn’t match earlier). The air had that salty-sweet smell you only get here, mixed with sunscreen and someone’s fruity drink already going strong.

Our guide — I think his name was Keoni — handed me a “Holokai Hooch” before we even left shore. It’s one of those local cocktails that tastes like vacation in a cup (sweet, a little dangerous). The music was mellow at first but picked up once we got moving, and people started talking across tables like old friends. There’s something about being out on the water off Honolulu’s coast that makes everyone loosen up. I remember the wind tangling my hair while the city lights slowly blinked on behind Diamond Head — not sure I’ve ever seen that shade of gold before.

Honestly, I didn’t expect to laugh so much. A group from Chicago tried to teach us their version of “cheers,” which turned into a whole thing with champagne splashes and some questionable dance moves (no judgment). Unlimited drinks helped, obviously. If you’re thinking about the Waikiki sunset cocktail sail, just know it’s less about perfect photos and more about feeling part of this weirdly happy floating party for an hour or so. I still think about that light fading over the water — it stays with you longer than you’d think.

Step-by-step itinerary

Day 1 — Sunset sail with open bar

• Board Holokai Catamaran barefoot
• Set sail for Waikiki sunset
• Enjoy unlimited drinks onboard
• Socialize and relax with crew
• Watch sunset over Honolulu coast

Top questions

Is there an open bar on the Waikiki sunset sail?

Yes, unlimited drinks are included—beer, wine, champagne, soft drinks, and signature cocktails.

How long is the Waikiki sunset cocktail sail?

The cruise lasts approximately 1.5 hours.

Are Friday night sails adults only?

Yes, Friday sunset sails are reserved for guests aged 21 and over.

Where does boarding take place?

You board directly from the beach in Waikiki—barefoot boarding is required.

Is parking available for this tour?

Validated parking is available at Embassy Suites Hotel for $15 (4 hours).

What drinks are served on board?

The open bar includes Maui Brewing beers, wine, champagne, soft drinks, and Holokai Hooch cocktails.

Is motion sickness aid provided?

Yes, motion sickness aid is included if needed during your sail.

What’s included

Your evening includes barefoot beach boarding onto the Holokai Catamaran for a 1.5 hour sunset cruise off Waikiki’s coast with unlimited drinks—beer, wine, champagne, soft drinks, plus local cocktails—and motion sickness aid if needed; validated parking at Embassy Suites Hotel is available for four hours; dry storage is provided for your belongings.