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    Sail Blue Hawaii

    5.0 (37 reviews)
    Open Open 24 hours
    Updated 2 months ago

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    Grey skies turned into a gorgeous sunset.

    ago It was a beautiful and relaxing experience with Captain Gaelyn on her sail boat. We watched a gorgeous sunset off the shores of Honolulu. She provided great communication, a prompt response to our inquiry, and clear instructions on meeting her. It was so wonderful to have a private sailing experience with friends. We would highly recommend sailing with Capt. Gaelyn, and we definitely look forward to our future sail together.

    Diamond Head
    Mike T.

    You're on the water. In Oahu. Just that alone is worth a star. You're Captain is a Kiwi, with a delightful personality, another star. You have the luxury to remain in stern, move about the yacht at leisure, head to bow, and feel the breeze brush across your face, while you spot sea turtles off port side, another 3 stars. Gaelyn, our Captain, has been sailing these waters for decades and has had this yacht for just over a decade - a 42 foot Beneteau beauty! She keeps the yacht clean, shares her cooler with you if needed and ensures your time spent on Kaikiwi is an absolute treasure!

    Emily Z.

    I took a lesson from Captain Gaelyn because I am not yet confident sailing off into unknown waters on my own. I brought along three people and they had a great time just hanging out while we cruised around the beautiful scenery during the lesson. Even though I'm ASA 101 and 103 certified, I still learned quite a bit from Captain Gaelyn in just our short lesson. She was patient and willing to do enough repetition of the maneuvers with me until I got comfortable. And everything she said was very informative. I very much appreciated her sailing style - little things like keeping a reef in the main and having all the lines tidy. Speaking of that, the boat is a beaut and is very well kept. Thank you Captain Gaelyn for a lovely experience.

    Heading out of Kewalo Basin.

    My fiance has wanted to learn how to sail for forever, so for his birthday, I thought what better gift than sailing lessons! I just had to find the right teacher. We couldn't have been happier to find that teacher in Captain Gaelyn!! She really knows her stuff and, equally important, knows how to teach. Her boat is impeccable, too. It was an absolute blast!! Can't wait to sail again with Captain Gaelyn!!

    Kelci L.

    My sister arranged a couple hour sailing trip while we were staying on Oahu for a family trip. I was a tad unsure about the idea of this because my 18 month old son would be coming along, and wasn't sure what to expect. Gaelyn is extremely knowledgeable about all things sailing and I felt extremely safe while on her boat. Her equipment is clean and the boat is lovely. Sailing was a huge highlight on our family trip, and I'm so glad we did it! I would highly recommend Gaelyn and Blue Sail Hawaii to anyone looking for something fun and different!

    Dawn T.

    I thought long and hard about sailing in Hawaii. Captain Gaelyn was very efficient in getting back to me and offering tons of information to finalize my adventure. She truly takes pride in what she does and has a beautiful vessel. Captain Gaelyn let's get involved in the learning process of sailing or you can just sit back and relax. Either way it was an experience of lifestyle. Thank you Captain Gaelyn!! We will never forget you. The dolphins were amazingly beautiful!!

    Misty F.

    Excellent, friendly service! Wonderful experience. Highly recommend for a relaxing, one-of-a-kind Hawaiian sunset.

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    Heath A.

    My wife and I definitely echo the other positive reviews of Capt. Gaelyn and her sailboat, the Kaikiwi. She took us out for a sunset sail on our 1st anniversary, and it was everything we could have hoped for. She was friendly and personal. Her boat was well maintained, and sailed perfectly. Highly recommend her! We will definitely sail with her again in the future.

    The trip was a great value and we are already planning a return trip for a whale excursion with Gaelyn.

    My wife and I did a learning Cruise where Gaelyn taught us the basics of sailing. She was a gracious host, great teacher with tons of patience. The trip was a great value and we are already planning a return trip for a whale excursion with Gaelyn. Gaelyn is super responsive, super flexible for anything you would want to do regarding a cruise.

    Roger S.

    Sailing along the south shore of Oahu at sunset with Capt. Gaelyn was the highlight of our trip to Hawaii. Her boat, named KaiKiwi (combining her love of the ocean (Kai) with her New Zealand roots (Kiwi), is a beauty. The weather was perfect with just enough clouds to ensure a beautiful sunset. Mahalo for a lovely evening.

    One of the more acrobatic of the pod of about thirty.
    B B.

    The highlight of our trip. A peaceful sail along the coast wit its of trivia thrown in. We were fortunate to be joined by dolphins for part of the trip.

    Us with our skipper Gaelyn!
    Ben O.

    Sailing with Gaelyn is fantastic! If you are looking for a true skipper who will give you the best possible experience. We booked our charter a few months in advance and she was prompt and informative in our correspondence. Her directions to the slip of the KaiKiwi were perfect and we had no trouble finding her. Our weather conditions were perfect and we set sail. The boat was kept in prime condition and Gaelyn has a easy spirit about her that makes it so comfortable to sail with her. We had great banter back and forth as we sailed back and forth in front of Honolulu. The experience we had was worth every penny and will be back for an inter island charter. Thanks again Gaelyn!!

    Capt. Gaelyn. Showed us the view today.

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    1 year ago

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    The pleasure was all mine. A hui hou.

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    8 years ago

    Loved ever moment, learned a lot, and can't recommend Capt. Gaylean enough. If you are in Hawaii give her a call

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    8 years ago

    If you are in Hawaii, you will not going to regret hiring Gaelyn! She is so helpful and her customer Service is top notch.

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    Ask the Community - Sail Blue Hawaii

    Review Highlights - Sail Blue Hawaii

    My wife and I definitely echo the other positive reviews of Capt.

    Mentioned in 9 reviews

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    Sail Blue Hawaii - tours - Updated August 2026

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