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Waikiki Afternoon Sail

Waikiki’s Best-Value Afternoon Sail – Open Bar, Diamond Head Views, & Direct Beach Boarding

At $50 per person with all drinks included, the Waikiki Afternoon Sail is the best-value experience on the water in Waikiki – and it isn’t close. Board our custom 45 foot catamaran directly from the sand, pop open a cold drink, and settle in as we sail the south shore of Oahu toward Diamond Head. No harbor, no shuttle, no crowds – just the open ocean and the warm trade winds & the most iconic views of the Pacific Islands.

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The Route: Waikiki to Diamond Head

We depart directly from Waikiki Beach and follow the trade winds blowing in from the northeast, sailing down the south shore of Oahu toward one of the most photographed landmarks in the world: Diamond Head. Along the way, you’ll pass the historic Waikiki Natatorium War Memorial, the Diamond Head Lighthouse, and the stunning coastline at Black Point. On a clear day, the green ridgeline of Molokai rises above the horizon some 40 miles to the west – a sight most visitors to Hawaii never get to see from this angle.

Open bar for $50? Yes, Really

Every seat on the Tradewind Sail comes with a full open bar. Beer, wine, our house cocktail, and non-alcoholic beverages are all included in your $50 ticket price – no extras, no cash bar, no surprises. Sip a cold beer as Diamond Head slides past, or raise a cocktail to the trade winds as the catamaran heels through the Waikiki swell. It’s a genuinely remarkable deal, and frankly the kind of thing you’d pay three times as much for almost anywhere else.

A Perfect ‘In-Between’ Activity for All Ages

The Waikiki Afternoon Sail is one of the most versatile activities on the island, at an intentional sweet-spot at 3PM. By mid-afternoon, the morning snorkels have returned to their hotels, the beach is at its liveliest, and the afternoon light on Diamond Head is nothing short of spectacular. Kids sail for free (aged 0-3), or at a discounted Keiki (kids) rate for $30. Families & groups get a shared experience that doesn’t require everyone to do the same activity at the same speed, and solo travelers get to see a side of Waikiki that most people who stay on land never get to experience. If you’re trying to figure out what to do between your morning activity and your evening luau reservation – this is it.

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Why Choose Holokai for Your Waikiki Beach Adventure?

There are several operators offering snorkeling on Oahu, so what makes Holokai different? A lot, actually.

Direct Beach Boarding – No Harbor Hassles

Most snorkel tours on Oahu depart from Kewalo Basin Harbor, requiring guests to take a shuttle or bus from Waikiki, check in at a crowded pier, and wait on a dock. With Holokai, you check in just steps from your hotel and board our catamaran directly from the beach. No shuttles. No industrial harbor. No bus rides. It’s the most convenient turtle canyon snorkel Waikiki experience available – and it’s the way a Waikiki beach adventure should feel.

A Luxury Catamaran, Not a Powerboat

The Holokai is a beautiful, custom-designed, handcrafted 49-passenger beach catamaran – not a cramped powerboat. With spacious seating, a shaded upper deck, and our famous netted splash area where you can hang over the water as we sail, there’s simply no comparison. Our honu snorkel catamaran experience combines the thrill of sailing with the magic of snorkeling. After your time in the water, relax on the nets with a drink as we sail the Waikiki coastline toward Diamond Head.

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The Holokai departs from the beach for all of our sails, so be sure to bring footwear that you can easily slip on and off! The specific beach for arrival and departure changes depending on the tides to ensure a safe boarding, so keep in mind that the departure spot may change and might not always be right outside the check in location at the Outrigger Reef Hotel (2169 Kalia Rd). The walk down to the beach may take from 5 to 10 minutes, a maximum of 0.3 miles down to the boat.

Any guests with mobility issues or are a slower walker: please call us at (808) 922-2210 to let us know after or before you book, so we can make the appropriate accommodations for your group, mahalo!

For large parties of 16 or more, please call our reservations line to book.