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.

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.

Motion Sickness Aid
Reef Safe Sunscreen
Alcoholic and Non-Alcoholic Beverages
Validated Parking at Embassy Suites Hotel ($15 for 4 hours)
Dry Storage
Bathroom

Shaded areas / sun-protective gear
Dramamine

1. Check-in at our office at the Outrigger Reef Hotel (2169 Kalia Rd.)
2. Walk down to the boat after check-in, and board directly from the beach
3. Depending on the weather either motor or sail from Waikiki Beach, and head down towards DIamond Head.
4. Sail / Motor around Diamond Head and enjoy beautiful views of the Lighthouse, Natatorium, and more!
5. Get dropped back off and deboard the boat directly from the beach.

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.

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.

After you check in at our office, 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!

Hats, sunglasses (sun protective gear)
Dramamine (if prone to sea sickness - we highly recommend non-drowsy)

Children under 18 MUST have an accompanying adult.

ALL GUESTS MUST bring an ID in order to enjoy alcoholic beverages from our on-board alcoholic bar.

Not suitable for those with heavily impaired mobility - to board the Holokai from the beach requires going up eight steps at the front of the boat & walking on loose sand at the beach.

Guests will receive a full refund if cancellation occurs 30 days prior to the private charter booking date. After this, cancellation before seven days of the scheduled charter will receive a full refund, less a 10% fee. Cancellation within seven days of the scheduled charter is non-refundable. Private charters are also subject to the no show, no call policy listed above.

A "No Show, No Call" on a reservation forfeits your right to receive a refund or rebooking and the full amount of the activity will be charged. Contact us by phone at: (808)-922-2210 or by email [email protected] to cancel your reservation. If you have a medical emergency less than 24 hours prior to your reservation, please call us to cancel and for details on how to receive a refund.

All reservations will receive a full refund or option to book to another available day if Holokai Catamaran cancels due to weather or unforeseen circumstances.