We're here to help
    Book online or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. Things to do in Haleiwa…/
    3. Water Activities/
    4. Sailing/
    5. Sail a Private Charter on Oahu's North Shore
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    [email protected](650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Product image 8
    Product image 9
    Product image 10
    Product image 11
    Product image 12
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Sail a Private Charter on Oahu's North Shore

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

    5.0 stars• 56 reviews
    From$917incl. taxes and fees

    Duration

    1.5 - 6 Hours

    Ideal For

    Up to 6 people

    Includes

    Private charter, Sailing, Crew

    Highlights

    Explore Oahu’s North Shore on a private sailing charter with options from 1.5 to 6 hours. Sail along the coast for sightseeing, with opportunities for sunset views, swimming, and snorkeling depending on your charter.

    • Choose a 1.5-, 3-, 4-, or 6-hour private charter for up to 6 people
    • Sail along Oahu’s North Shore coastline with an experienced crew
    • Spot natural landmarks like Waimea Bay from the water
    • Plan a sunset sail based on your charter time
    • Anchor at Waimea Bay on half-day and full-day charters when weather permits
    • Snorkel on half-day and full-day charters when weather permits

    Things to know

    The captain may cancel or shift the booking time/day due to inclement weather.

    Cancellation Policy

    Cancel at least 7 days before for a refund on private charters. A 20% fee applies to any canceled private charters. No-shows and late arrivals are charged the full price. Full refund if the operator cancels due to weather or other unforeseen circumstances.

    FAQs

    Meet at Haleiwa Harbor (Pier 300, slip 322). Arrive 10 minutes before your sail time for a meet-and-greet and safety briefing before heading out.

    Park anywhere in the parking lot and walk to Pier 300. Walk to the very end of Pier 300 to the T-bone; the boat ("Keet") will be on your right.

    Yes. The captain may cancel or shift your booking time/day due to inclement weather.

    Experience provided by North Shore Sailing Adventures
    Experience provided by North Shore Sailing Adventures

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #M2D5WA

    One & Half Hour Private Charter

    $917.70

    Price includes up to 6 people

    0

    Three Hour Private Charter

    $1,147.12

    Price includes up to 6 people

    0

    Four Hour Private Charter

    $1,376.54

    Price includes up to 6 people

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    56 reviews•Google Maps

    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

    Would recommend to anyone. Nice experience and the staff was very nice and ressourceful.

    Photo of David Belanger

    David Belanger

    February 10, 2026

    Review 1 of 1
    5/5

    Would recommend to anyone. Nice experience and the staff was very nice and ressourceful.

    Photo of David Belanger

    David Belanger

    February 10, 2026

    Great for groups

    Thumbnail
    Private Boat ChartersUp to 6

    Private Sunset Sail with Views of Haleiwa Coast

    $1,107.10
    Thumbnail
    Private Fishing ChartersUp to 6

    Private Offshore Fishing Charter on Oahu's North Shore

    From$992
    Thumbnail
    Private Boat ToursUp to 6

    Private Sunset Cruise in Haleiwa with Local Stories

    From$554

    Nearby activities

    Thumbnail
    Dolphin WatchingUp to 6

    Dolphin Watching Cruise on Oahu's North Shore

    From$1,147
    Thumbnail
    SailingUp to 6

    Full-Day Private Sailing Charter to Waimea Bay

    $1,937.42
    Thumbnail
    Swimming with SharksUp to 12

    North Shore Shark Cage Dive in Haleiwa

    From$143/ person
    Thumbnail
    Sailing

    North Shore Sunset Sail from Haleiwa Harbor

    From$100/ person
    Thumbnail
    Snorkeling

    Haleiwa Snorkeling & Sailing Tour, North Shore

    From$160/ person
    Thumbnail
    Swimming with Sharks

    Open Ocean Shark Snorkel with Researchers

    From$170/ person