Waikiki Catamaran Sail with Open Bar: Afternoon Trade Winds

Sail toward Diamond Head with a cold drink already in your hand

An afternoon catamaran sail from Waikiki Beach on Oahu with a fully stocked open bar, departing at 3pm for a 1.5-hour voyage toward Diamond Head. You board directly from the sand—no shuttle, no harbor, no wasted time—and the boat carries near 360-degree views from a spacious 45-foot hull. Beer, wine, cocktails and non-alcoholic drinks are included in the ticket price, along with reef-safe sunscreen, motion sickness aid and parking validation.

The Experience

What's the fastest way to get on the water in Waikiki without losing half the afternoon to logistics? Board straight from Waikiki Beach at 3pm—check in 30 minutes prior at The Outrigger Reef, then a 5–10 minute walk across the sand puts you on the catamaran. The boat is a 45-foot vessel with sightlines in nearly every direction, and the trade winds that make this coast famous are what fill the sails. You'll sail toward Diamond Head, watch for dolphins and sea turtles, and the whole thing wraps by 4:30pm. The open bar runs the full 1.5 hours: beer, wine, cocktails, soft drinks, all included.

Barefoot boarding means wear shoes you can slip off fast. The beach walk is short but it crosses sand, and there are stairs when you board from the shore, so move at your own pace—if you have mobility questions, call ahead at [phone] and they'll set things up. Parking validation covers four hours at Embassy Suites valet for $15 if you drive; public transit stops are nearby if you don't. Everyone under 18 needs a parent or guardian on board and a waiver signed 24 hours before. Families bring kids ages 4–12 at a reduced rate, and infants sail free.

What’s included

• The sail includes a fully stocked open bar with beer, wine, cocktails and non-alcoholic drinks.
• reef-safe sunscreen.
• motion sickness aid.
• dry storage for your belongings.
• and parking validation at Embassy Suites valet ($15 for four hours if you drive).

Good to know

Easy physical levelPublic transport nearbyNot for back problems

Operated by Holokai Catamaran

Is this one for you?This works best for afternoon visitors who want to be on the water without eating up the whole day—the 3pm departure and 4:30pm return fit between lunch and dinner, and the direct beach boarding means you skip the usual harbor shuffle. Small groups and families travel together on the same boat, so it's social without being crowded.

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Top questions

Can I really board the catamaran straight from Waikiki Beach without taking a shuttle?

Yes. Check in at The Outrigger Reef Waikiki Beach Resort 30 minutes before departure, then walk across the sand to the boat—the walk takes 5–10 minutes at most. No harbor, no bus, no detour.

What's included in the $50 ticket besides the sail?

The open bar covers beer, wine, cocktails and non-alcoholic drinks for the full 1.5 hours; reef-safe sunscreen and motion sickness aid are also included. If you drive, parking validation at Embassy Suites covers four hours for $15.

How long does the whole thing take from start to finish?

Depart at 3pm and return by 4:30pm—the sail itself is 1.5 hours, and you'll be back on the beach in time for dinner plans or to catch the sunset from shore.

What can I see from the boat?

The catamaran sails toward Diamond Head along Oahu's coastline with near 360-degree views from the 45-foot deck. Dolphins and sea turtles show up regularly in their natural habitat, though sightings are never guaranteed.

Can I bring my kids?

Yes. Children ages 4–12 sail at a reduced rate, infants sail free, and anyone under 18 must be accompanied by a parent or guardian over 18. A waiver signed by the parent or guardian is required 24 hours before departure.

What do I need to wear or bring?

Wear shoes you can remove easily since boarding is barefoot. You'll walk across sand and climb stairs to get on the boat. Reef-safe sunscreen is provided, but bring sunglasses and a hat if you want them. A towel and change of clothes are smart if you're sensitive to salt spray.