For more than twenty-five years, our family has been raising sails off the Ko Olina Marina and sharing the same stretch of leeward Oʻahu coastline we grew up on. Here’s how it started — and who you’ll meet when you step aboard the Hololeʻa Kai.
Our Story
Over two and a half decades ago, Todd Pickering and Mick Riegel took their love of the ocean to the ultimate test of sharing their passion with visitors from across the globe. Todd was a sailor at heart, and Mick a diver by nature. The two friends created a passive dolphin swim in the wild, shared SNUBA, and now raise sails on their beautiful 53′ sailing catamaran, the Hololeʻa Kai.
Hololeʻa kai means to sail freely with the ocean, as the two founders have done — moving with the ebbs and flows of the market, federal permissions, and global challenges. As Mr. Riegel has retired back in California, Todd Pickering continues the company with his Hawaiian-grown family, each working as Kitchen Manager, Bookkeeper, and Captains at the helm. The company is truly a family owned and operated business.
Frequently Asked Questions
Morning Catamaran Snorkel & Sail
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Yes, our Snorkel and Sails include all equipment from life vests to fins, snorkel and masks. We even have special fins and masks for the little ones!
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Yes, we have low prescription to high prescription lenses for seeing the fish super clear! Ask our crew, and we will be happy to help
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Our tours sail up the coastline for a view of the Waianae mountain range, and sail as far as Maile Point, however, our snorkel sites are within a couple miles of Ko Olina Resort as the best reef is found right here! We choose one of two of our locations and decide by sea conditions, current, swells and winds as to which site is the best for the tour. Our snorkel sites are about a quarter mile off shore.
Afternoon Catamaran Snorkel & Sail
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Good question. The morning typically has the calmest and smoothest ocean and wind conditions; however, if opting for the afternoon- you’ll have plenty of overhead lighting for the reef and fish, and when you exit the water, the warm Hawaiian sunshine will warm you up quickly.
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Our friendly sea creatures are often easier to spot in the morning due to the generally smoother ocean, however, since we are looking for wildlife, it is entirely unpredictable. Both tours have a great shot at enjoying the wildlife at a respectful distance.
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No, you don’t have to be a great swimmer. In fact, since snorkeling is really about remaining calm and putting your face in the water to view the fish, it is best if you are generally comfortable in the water, and can practice breathing through your mouth, rather than nose. This will help you be comfortable while wearing a mask and float calmly to enjoy the fish and reef below you.
Oʻahu Sunset Sailing Cruise
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In Hawaii, we typically don’t observe dress codes, as everyone is coming from the beach, surfing, or otherwise, a typical beach culture. However, there are some who want to take some beautiful pictures with the golden sunset and dress in relaxed resort wear or aloha shirts for men, so they look good in those IG reels. Please remember that our boat is a barefoot boat, so please leave the heels at home or in your car for after the sail.
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The green flash is often seen on our boat on clear evenings.
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Yes, we love being part of your love story, please contact our reservations team to see what details we can help with so that you have an evening to remember.
Come Sail With Our Family
Whether it’s your first time in a mask or your tenth trip to the islands, there’s a spot for you on the Hololeʻa Kai. Our crew handles the gear, the galley, and the sails — you just show up barefoot.
Questions? Contact our reservations team today.