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Waikiki Afternoon Sail

Waikiki’s Best-Value Catamaran Sail – Walk from your Hotel, Board from the Beach

The Holokai Waikiki Afternoon Sail is a 90-minute, open-bar catamaran sail departing directly from Waikiki Beach, Honolulu, Hawaii, featuring scenic trade wind sailing toward Diamond Head.

Looking for a catamaran tour near your Waikiki hotel this afternoon? The Holokai Afternoon Sail is Honolulu’s most accessible and best-value sailing experience – departing directly from Waikiki Beach, steps from the strip’s top hotels. At $50 per person with a full open bar included, there’s nothing like it in Waikiki. Check-in is at Outrigger Reef Waikiki (2169 Kalia Rd), and most central Waikiki hotels are under a 10-minute walk away. No harbor runs, no shuttles – just walk down, board, and sail toward Diamond Head.

Walking Distance from Your Hotel

Whether you’re wrapping up a morning hike or kicking off your evening plans, our check-in at the Outrigger Reef Waikiki Beach Resort (2169 Kalia Rd) is incredibly convenient. It’s an easy 10-minute walk or less from most central Waikiki hotels.

What is the Waikiki Afternoon Sail?

The Waikiki Afternoon Sail is a 90-minute scenic ocean cruise along Oahu’s south shore aboard the Holokai beach catamaran. Guests sail with the trade winds toward the iconic Diamond Head crater, taking in views of the historic Waikiki Natatorium, Diamond Head Lighthouse, and the stunning Black Point coastline – all while enjoying an included open bar.

It’s the perfect afternoon activity between your morning adventures and evening plans. And at $50 per person all-in, it’s the best-value sailing experience on the water in Waikiki. Comparable open-bar catamaran sails in Honolulu can cost significantly more. Not here.

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 Oahu catamaran tours require guests to take a shuttle to Kewalo Basin Harbor. With Holokai, you check in steps from your hotel and board directly from Waikiki Beach. We depart from the shoreline nestled between Fort DeRussy and the Royal Hawaiian Hotel – the most convenient departure point for any boat tour in Waikiki.

A Premium Catamaran, Not a Powerboat

Spacious seating, a shaded upper deck, and our famous netted splash area make the Holokai experience a cut above any powerboat tour. Feel the ocean spray and relax on the nets with a cold drink while we sail the Honolulu coastline.

Open Bar at an Incredible Price

Every seat on the Afternoon Sail comes with a full open bar – beer, wine, our signature “Holokai Hooch” cocktail, and non-alcoholic options included. No extras, no cash bar. Just $50 all-in.

How Beach Boarding Works

Check-in is at Outrigger Reef Waikiki Beach Resort, 2169 Kalia Rd. From there, it’s a 5-10 minute walk (max 0.3 miles) to the beach boarding point, which shifts slightly with the tides to ensure the safest boarding every time. Our crew guides you the whole way – just bring footwear you can slip on and off.

Guests with mobility concerns or slower pace: call us at (808) 922-2210 before or after booking and we’ll make the right arrangements for your group. Mahalo!

For groups of 16 or more, please call our reservations line or email us at [email protected] to book.