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  1. The 12 Most Breathtaking Places to Hot Air Balloon in the United States
  2. North Shore Sailing Adventures

    5.0 • 59 reviews
    Haleiwa, HI

    Experience Oʻahu’s North Shore the way it was meant to be—under sail. Aboard KEET, a 40-foot Coast Guard–inspected trimaran inspired by Polynesian voyaging canoes, Captain Porter Turnbull and his Hawaiian Searunner crew blend gene...

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    Book North Shore Sailing Adventures

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    Half-Day Private Sailing Charter on Oahu's North Shore

    Sail the North Shore with a naturalist and seasonal whale listening

    $1,660.65
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    Full-Day Private Sailing Charter to Waimea Bay

    Private 6-hour sail to Waimea Bay for up to 6 people

    $1,937.42
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    Private Dolphin Watching Sailboat Charter in Haleiwa

    Private North Shore sail to spot dolphins and see Waimea Bay

    From$1,147
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    Sail a Private Charter on Oahu's North Shore

    Private sailing charter on Oahu’s North Shore for up to 6 people

    From$1,147
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    Private Sunset Sail with Views of Haleiwa Coast

    Sail Oahu's North Shore at sunset on a private 3-hour charter for up to six.

    $1,107.10$1,040.67

    Review summary

    5.0
    Excellent
    59 reviews•Google Maps
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    Captain Porter and his crew, particularly Chad and Will, have built something really special here. Families consistently rave about the intimate, private experience - these aren't crowded cattle boats, with just one family or small groups of up to six guests at a time. The captains bring genuine enthusiasm and deep knowledge of sailing and marine life, expertly navigating to spots where guests regularly encounter dolphins, sea turtles, and during whale season, humpback whales. Multiple reviewers call their trip the highlight of their entire Oahu vacation. The operation runs smoothly from start to finish. Communication is excellent, with quick responses to questions and clear instructions. The crew is described as laid-back yet professional, creating a relaxed vibe without any pressure or time constraints. They provide thoughtful touches like homemade lunches, cold drinks, and even raincoats when weather shifts. The trimaran offers plenty of deck space for snorkeling, swimming, and dolphin watching, though there's minimal shade coverage, so bring sun protection. Whether you're booking a snorkeling adventure, sunset sail, or even a proposal, the consensus is clear: this experience delivers unforgettable memories and genuine value.

    What people are saying

    Review 1 of 4
    5/5

    We could not have asked for a better sunset selling experience! Thank you Captain Porter and Ashley! We would come back out with you again and again and again.

    Photo of Sam Mikelic

    Sam Mikelic

    July 1, 2026

    Review 1 of 1
    5/5

    We could not have asked for a better sunset selling experience! Thank you Captain Porter and Ashley! We would come back out with you again and again and again.

    Photo of Sam Mikelic

    Sam Mikelic

    July 1, 2026