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Private Sailing

What better way to celebrate your special event than sailing the waters of Waikiki on your own private sail! As a large group, we want to ensure you and your guests can relax and enjoy the boat freely. Whether you’re celebrating a birthday, anniversary, graduation, family reunion, wedding or just a way to spend the day – let us help you create memories and an experience of a lifetime!

From proposals to family reunions to corporate events, our various sails throughout the day offer the perfect setting for every occasion!

Upgrade to an all-inclusive package on any of our sails with catering options and custom bar selections. Our crew specializes in helping to create the most memorable experience for any occasion.

a group of people in a boat on a body of water
a group of people in a pool of water

Bachelorette / Bachelor Parties

a group of people on a beach posing for the camera

Looking for a fantastic event for your bridesmaids or groomsmen for destination weddings or welcoming your guests to Hawaii for your wedding weekend? Kick off your pre-wedding celebrations with an open bar and amazing jams – add the open ocean and it’s sure to be a good time!

Family Reunions

person jumping into the ocean from a catamaran

Whether it’s your annual get together or it’s been a while since you’ve seen the aunties, gather the family together for snorkeling with the honu and an afternoon on the waters of Waikiki. Add some delicious pupus and you’ve got something for the uncles, too!

Corporate Events

a man and a woman taking a selfie

Team building, incentive trips, company retreats, and networking events – a day on the water is just what they need to put this year’s trip on their top 10 list! A private sail in Waikiki is the perfect umbrella to top off your tropical itinerary cocktail.


Turtle Canyon Adventure Sail

a large reptile in front of a body of water


9AM and 12PM Daily
2.5 Hours
Up to 34 Passengers
Weather Dependent

What better way to start your day than to
slip into the refreshing waters of Hawaii and swim with the turtles, fish, and other marine life? All of our crew are experienced divers and can help you realize the beauty below the surface. Our crew specializes in showing you not only turtles but also hidden creatures such as tako (octopus) or wana (sea urchin). Light, individually packaged snacks such as chips, cookies, and granola bars are provided as well as complementary drinks such as water, soda, or juice. As well as all gear- including snorkels, masks, and snorkel vests. Alcoholic beverages are available for cash purchase.

Tradewind Sail

a boat on a body of water


3PM Daily
1.5 Hours
Up to 49 Passengers

This sail gives you an opportunity to see Oahu from a different perspective at a great value! Our normal tradewinds blow from the northeast making for a spectacular view from the boat as you pass the Natatorium and Diamond Head lighthouse. Blackpoint, Koko Head and Koko Crater are in the near distance and if you have good eyesight, the island of Molokai can be seen on clear days, some 40 miles away! Alcoholic and non-alcoholic beverages are available for cash purchase or add an open bar for $400.00.

Sunset Sail



5PM Nightly (5:30PM March-September)
1.5 Hours
Up to 49 Passengers

You’re in for a treat with our top-notch sail, perfect for families and friends seeking a blast! This sail is completely open bar; so think juices, sodas, water, wine, the coolest local and domestic beers, zesty hard seltzers, and our famous “Holokai Hooch.” So kick back, chillax, and let our awesome crew hook you up with a cold one while you soak in the epic sunset vibes!

Fireworks Sail

fireworks in the sky


7PM Fridays ONLY (7:30PM April-August)
1 Hour
Up to 49 Passengers

Stunning fireworks display seen from the water, a cold drink in your hand, and the ocean air breezing by- what more is there to say? Book early to reserve seats- with only one sail a week, the Fireworks Sail sells out fast! Alcoholic and non-alcoholic beverages are included!

Ash Scattering

a boat on a body of water


7:30AM Departure
1 Hour
Up to 49 Passengers

Embrace the serene spirit of Hawai’i with our ash scattering private charter, a deeply respectful journey to honor and celebrate the lives of your loved ones who have passed. Departing from the shores of Waikiki, our catamaran will take you out to a serene sanctuary, surrounded by the gentle waters of Hawaii where we will gather to continue the ceremony. This journey, carefully crafted with the aloha spirit, offers a safe and sacred space for you to find comfort, closure, and beauty in the memories that you will cherish forever with them in your hearts. Mahalo nui loa for considering our ash scattering private charter – a serene sail where love, memories, and the spirit of Hawai’i unite in a celebration of life’s journey.

Ready to Book?

Contact us to schedule your Private Sail. For details on large party reservations with Holokai VIP service, please call our reservations line.