1. Sail Blue Hawaii

    1. Sail Blue Hawaii

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    Honolulu, HI

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    Sail Blue Hawaii

    5.0 (37 reviews)
    Open Open 24 hours
    Updated 1 month 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.

    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.

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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.

    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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    10 years ago

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    The pleasure was all mine. A hui hou.

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    7 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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    MANA sunset cruise from Ko Olina - the absolute highlight of our trip!!!…read more We are no strangers to Catamaran excursions - trips in the British Virgin Islands, Greece, and the U.S. Virgin Islands. By far, Captain Travis and First Mate Taylor were exceptional, leaving no detail to chance. We were warmly greeted with a drink and were given a very thorough safety briefing. Both were meticulous in their duties to their craft as well as to their guests. The catamaran was immaculate, an outstanding demonstration of the care and maintenance it receives - impressive for a 2008 Cat. Thanks MANA and crews for your care and concern. We had only 5 of us aboard ( they allow a maximum of only 6) which really enhanced the experience. As we got underway drinks were served and then came what I thought was going to be a sampling of local snacks. No, it was a full dinner made by Taylor that was some of the freshest, best food we have had on the Island, followed by a dessert second to none. The other guests dietary restrictions were taken into consideration and we sailed (and for a portion of the trip we were under full sail & not motoring) around with soft Hawaiian reggae playing. The two hours flew by.... We were regaled with stories of the Islands and some very interesting facts. Sure there are less expensive, far more crowded sunset tours... but NOTHING compares to this one. It was worth every cent. When we return we will have already booked this trip before we board our again! Do yourself a favor, splurge on a really personal Hawaiian experience and book this trip. You will be richly rewarded & have memories for years to come! There may be no traffic jams on the extra mile... but you will find on this excursion, Captain Travis & First Mate Taylor are on the extra mile & demonstrate what the extra mile should look like! A very important note - we recommend if you are coming from the Waikīkī area that you plan on leaving early and planning a light lunch at Ko Olina - the Monkeypod, or one of the restaurants in the hotels. The traffic leaving Waikiki in the afternoon is horrible in the afternoon and could take several hours to navigate to Ko Olina.

    Absolutely must do if you're looking for an excursion on the island. The boats are beautiful, the…read moreviews are insane, and the food and drinks are fire. We had Masa and Lia as our crew on board and we LOVED hanging out with them. They were constantly answering all of our questions and serving up the best drinks. Their service truly made our experience. This company has high reviews for a reason. Highly highly recommend booking.

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    We had such a blast on our submarine tour! The crew were all very nice and professional, and the…read moretour guide made great jokes and was very friendly. The ocean was clear and beautiful the day we went. We learned a lot about coral preservation and the animals while on the tour too. I usually do not like close quarters, but I was comfortable the whole time. It's a very roomy submarine. Having been, I feel like everyone should go at least once! We saw lots of different fish, 2 turtles (Timmy and Tina), an eagle ray, and the other side of the sub saw a shark-very cool!

    SO i'm a little bit embarrassed to write this review, but I must because I was so impressed with…read morethe professionalism from all of the staff. If it hadn't been for the care and compassion of Maya, I probably would've cried. I get motion sickness, but my kids were so excited about going on the submarine finally that I took Dramamine and threw caution to the wind. However, after the 15 to 20 minute boat ride over to the submarine, I'm sure my face was green. Although the submarine itself was 10 times more stable and calm and felt like the interior of an airplane, I was very concerned I was going to get sick in front of lots of strangers and had to exit the submarine very quickly. I left my tween kids there to experience the submarine by themselves, which is fine because my oldest son is on two swim Teams and basically a lifeguard. However, the boat had to come back and get me off the top of the submarine and it was very embarrassing and once again, I cannot say enough about how well the staff handled it and didn't make me feel silly. or stupid at all. I even bought some of the photos to laugh about the incident later. We had already gotten the military discount, but they offered to refund my portion of the submarine ride, which I very much appreciated. I would recommend this company to all of my friends. My sons loved seeing the 9 sea turtles & Hawaiian wildlife.

    Sail Blue Hawaii - tours - Updated July 2026

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