Waikiki: 3pm Tradewind Sail with Open Bar & Marine Life

Summary

Waikiki sailing afternoons with open bar ocean wildlife moments

You’ll step barefoot onto the Holokai catamaran for a relaxed 1.5-hour Waikiki sail with open bar drinks included. Watch for dolphins or humpback whales (in season), feel the tradewinds on your face, and share easy laughs with local crew as Honolulu slips away behind you. It’s laid-back, salty-air fun — perfect if you want an afternoon that feels both lighthearted and quietly memorable.

What’s the experience like?

“You gotta keep your eyes sharp — sometimes the dolphins like to play tricks,” our captain grinned as we shuffled barefoot across the sand toward the Holokai. I’d barely had time to brush the salt off my ankles before we were wading out, shoes dangling from my hand, trying not to laugh at how clumsy I looked. The sun was still warm but gentle, not that mid-day glare, and there was this faint coconut sunscreen smell everywhere — maybe from us or just the boat itself. I liked that.

The crew made it feel like you were just tagging along with friends who happened to know a lot about Oahu’s coastline. At some point, one of them pointed out a green sea turtle bobbing near the surface (I almost missed it — honestly looked like a floating log until it blinked). We kept scanning for whales — apparently December through March is when they show up most — but even without them, watching the city shrink behind us and feeling that tradewind whip around was enough. Drinks started coming around pretty quick; Mai Tai in hand, I leaned back against the rail and tried not to spill anything when we hit a bumpy patch. There’s something about being out there where you can’t really hear anything except water and laughter.

I’d read somewhere you might get another go if you don’t see whales — which is cool, though honestly I didn’t mind just floating along with no real plan except maybe catching a glimpse of something wild. Boarding from the beach felt less formal than those big harbor cruises; we walked maybe ten minutes down from where we parked at Embassy Suites (they validate your parking, which helps), and then it’s straight onto the sand. Not everyone loves getting their feet sandy before a boat ride but… I dunno, it felt right for Waikiki.

Step-by-step itinerary

Day 1 — Afternoon tradewind sail with open bar

• Arrive at designated beach
• Walk 5 to 10 minutes to boat
• Board the Holokai sailboat
• Enjoy 90-minute sail around Oahu
• Watch for dolphins, whales, sea turtles
• Take photos of marine life
• Enjoy open bar until 8/31/2025
• Return to beach and disembark

Top questions

How long is the Waikiki 3pm Tradewind Sail?

The sail lasts approximately 1.5 hours.

Is an open bar included in this Waikiki sailing tour?

Yes, open bar drinks are included with general admission until August 31, 2025.

Where does the Holokai catamaran depart from?

The departure beach varies based on tides but is within a short walk (up to 0.3 miles) from central Waikiki hotels.

Can I see whales or dolphins on this tour?

You may spot humpback whales from December to early March and dolphins year-round, but sightings aren’t guaranteed.

If I don’t see whales during whale season, can I join again?

Yes, if you don’t spot whales between December and March on the 3pm sail, you can join again at no extra cost after validating at their office.

Is parking provided for this Waikiki sailing trip?

Parking validation is available at Embassy Suites Valet for $15 (up to 4 hours).

Do I need special footwear for boarding?

No special footwear is required; bring shoes that are easy to slip off since boarding is directly from the beach.

Are there any physical requirements for joining?

Guests must be able to walk on sand and up stairs when boarding; not recommended for travelers with spinal injuries.

What’s included

Your afternoon includes dry storage for belongings, reef-safe sunscreen onboard, motion sickness aid if needed, all alcoholic and non-alcoholic drinks from the open bar (with general admission), plus parking validation at Embassy Suites so you can relax about logistics before setting sail along Waikiki’s coast.