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    1. Local experiences/
    2. Haleiwa, HI/
    3. Water Activities/
    4. Sailing/
    5. Sunset Sailing Adventure
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    Sunset Sailing Adventure

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

    From$1,000

    Duration

    3 Hours

    Ideal For

    Up to 6 people

    Includes

    Private charter, Sunset sail

    Highlights

    Set sail on a 3-hour private sunset cruise along Oahu's North Shore. Unwind as the sky glows with vibrant colors and capture memorable views from the water.

    • Sail the North Shore during golden hour
    • Relax on a leisurely 3-hour cruise
    • Watch the sky glow with vibrant hues
    • Capture unforgettable photos at sunset
    • Enjoy a private charter for up to six

    Cancellation policy

    Full refund with 72 hours' notice. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows and late arrivals are charged in full. Voucher bookings canceled within 72 hours forfeit vouchers. Private charters require 7 days' notice for refund; 20% fee applies to canceled private charters.

    Meeting location

    Pier 300 Haleiwa Boat Harbor Haleiwa, HI 96712

    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

    Reference #WQBT6F

    Private Charter

    $1,000

    Price includes up to 6 people

    1

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    5.0 stars• 56 reviews

    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 5
    5/5

    Me and my family decided to do a last min whale watching excursion as we read it is a great experience for those visiting Hawaii. Since we were visiting North shore for just the day, I was disappointed to know that all bookings happen in advance and it's best to book excursions ahead of time. I still decided to try my luck and landed up contacting North Shore Sailing Adventures and left a vm fully expecting to not receive a positive response. But to my surprise I received a call from a very pleasant lady Annastacia stating that we could sail the same afternoon as they had an opening. The entire booking process was easy with clear instructions on how to get to the pier. As we arrived at the pier at 3 pm, little did we know that this private sail would be the highlight of our trip. The kids were beyond happy to set sail and the entire team at NSSA was warm n welcoming. Captain Porter was very knowledgeable about whales and he patiently taught our kids on how to look out for whales, made them hear whale sounds and answered every question they had about whales. We spotted many whales on our 3+ hour sail and the icing on the cake was the amazing whale sightings we saw towards sunset.. Captain Porter n his crew spotted them and we were at the right place at the right time.. it almost felt like the whales had put on a show just for us, with them jumping out of water several times and doing flips. The whales truly seemed to have enjoyed our attention and the kids were beyond thrilled with everything they experienced. I HIGHLY recommed sailing with NSSA as Captain Porter and his crew ensure you have a great time. It surely was non-commercial and felt like a more personal experience for us that our entire family will never forget. "Because when you stop to look around, life is pretty amazing!" Mahalo North Shore Sailing Adventures - until we meet again.

    Photo of Mona Panjwani

    Mona Panjwani

    4 years ago

    Review 1 of 1
    5/5

    Me and my family decided to do a last min whale watching excursion as we read it is a great experience for those visiting Hawaii. Since we were visiting North shore for just the day, I was disappointed to know that all bookings happen in advance and it's best to book excursions ahead of time. I still decided to try my luck and landed up contacting North Shore Sailing Adventures and left a vm fully expecting to not receive a positive response. But to my surprise I received a call from a very pleasant lady Annastacia stating that we could sail the same afternoon as they had an opening. The entire booking process was easy with clear instructions on how to get to the pier. As we arrived at the pier at 3 pm, little did we know that this private sail would be the highlight of our trip. The kids were beyond happy to set sail and the entire team at NSSA was warm n welcoming. Captain Porter was very knowledgeable about whales and he patiently taught our kids on how to look out for whales, made them hear whale sounds and answered every question they had about whales. We spotted many whales on our 3+ hour sail and the icing on the cake was the amazing whale sightings we saw towards sunset.. Captain Porter n his crew spotted them and we were at the right place at the right time.. it almost felt like the whales had put on a show just for us, with them jumping out of water several times and doing flips. The whales truly seemed to have enjoyed our attention and the kids were beyond thrilled with everything they experienced. I HIGHLY recommed sailing with NSSA as Captain Porter and his crew ensure you have a great time. It surely was non-commercial and felt like a more personal experience for us that our entire family will never forget. "Because when you stop to look around, life is pretty amazing!" Mahalo North Shore Sailing Adventures - until we meet again.

    Photo of Mona Panjwani

    Mona Panjwani

    4 years ago

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