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Waikiki Afternoon Sail

Waikiki’s Best-Value Afternoon Sail & Diamond Head Catamaran Cruise

Sail the south shore of Oahu aboard the Holokai beach catamaran on an afternoon cruise that delivers big views, cold drinks, and zero hassle. Located just minutes offshore from the heart of Waikiki, the Holokai Afternoon Sail is Honolulu’s premier way to experience the island from the water in the middle of the day. When you join our Waikiki catamaran sail, you’re not just taking a boat ride. You’re boarding a premium catamaran directly from the sand, sailing toward the iconic Diamond Head crater, and returning with memories that last a lifetime.

What is the Waikiki Afternoon Sail?

Our afternoon sail is a scenic, warm-water ocean cruise that follows the trade winds down the south shore of Oahu. The warm sunshine and spectacular coastal views make it the perfect midday watersport activity year-round. Unlike many boat tours that require long drives or crowded harbor check-ins, our Waikiki catamaran is remarkably accessible.

On any given afternoon, guests enjoy the most iconic views of the Pacific Islands, including the historic Waikiki Natatorium, the Diamond Head Lighthouse, and the stunning Black Point coastline. It is the perfect “in-between” activity to fill the gap between your morning adventures and your evening plans. At just $50 with an open bar included, it’s the best-value experience on the water in Waikiki.

Why Choose Holokai for Your Waikiki Beach Adventure?

There are several operators offering boat tours in Honolulu, so what makes Holokai different? A lot, actually.

Direct Beach Boarding – No Harbor Hassles

Most catamaran 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 Waikiki sand. We are a true beach-boarding catamaran, taking off right from the world-famous shoreline nestled between Fort DeRussy and the Royal Hawaiian Hotel. Centrally located near the Outrigger Reef, Sheraton Waikiki, and Hilton Hawaiian Village, our departure spot means no shuttles, no industrial harbor, and no bus rides. It’s the most convenient Waikiki boat tour experience available – and it’s the way a beach adventure should feel.

A Premium 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. Relax on the nets with a drink as we sail the Honolulu coastline toward Diamond Head.

An Unbeatable Open Bar Value

Every seat on the Waikiki Afternoon Sail comes with a full open bar. Beer, wine, our signature “Holokai Hooch” cocktail, and non-alcoholic beverages are all included in your ticket price — no extras, no cash bar, no surprises. At $50 per person all-in, this is genuinely the best-value catamaran sail in Waikiki. Comparable open-bar sailing experiences on the island usually require you to pay a premium. We’re at $50.

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.