Sail Blue Hawaii LLC
Sail Blue Hawaii LLC
5
Boat ToursWater SportsPrivate ToursDolphin & Whale Watching
12:00 AM - 11:59 PM
Monday
12:00 AM - 11:59 PM
Tuesday
12:00 AM - 11:59 PM
Wednesday
12:00 AM - 11:59 PM
Thursday
12:00 AM - 11:59 PM
Friday
12:00 AM - 11:59 PM
Saturday
12:00 AM - 11:59 PM
Sunday
12:00 AM - 11:59 PM
Full view
About
Feel the tradewinds blow and delight in dolphins playing in the bow wake as you set sail. Charter options are limitless: sailing, sailing lessons, sunset cruise, ash scattering, saying "I do", multi-day charters, corporate fun(ctions), custom cruises...For Sail Blue Hawaii, the horizon is no limit.
Honolulu, Hawaii
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Sail Blue Hawaii LLC
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
5.0
188 reviews
Excellent
185
Very good
2
Average
0
Poor
1
Terrible
0
Jeffrey M
9 contributions
Dec 2020 • Couples
This is the perfect honeymoon/couples night activity. It's kid friendly, but I don't know why you'd waste something this intimate and romantic on people who wouldn't appreciate it (i.e., kids).
My wife and I took a 2.5 hour sunset sailboat ride with Gaelyn and it was a really wonderful experience. The views of the city, the landscape, and the sunset are stunning. You also get to see people surfing and parasailing. Gaelyn explained a bit to us about how sailing works, and talked about how she got into it and how she got her boat (sailed it all the way from Mexico to Hawaii!).
The trip was very relaxed. We left from Kewalo Harbor, sailed along Honolulu to Diamond Head, and then much of the way back. By then the sun was setting, and we sat in the same spot for 20 minutes as the sun disappeared behind the horizon. Gaelyn took some really nice pictures of us ("it's my second job" 😆).
My wife and I took a 2.5 hour sunset sailboat ride with Gaelyn and it was a really wonderful experience. The views of the city, the landscape, and the sunset are stunning. You also get to see people surfing and parasailing. Gaelyn explained a bit to us about how sailing works, and talked about how she got into it and how she got her boat (sailed it all the way from Mexico to Hawaii!).
The trip was very relaxed. We left from Kewalo Harbor, sailed along Honolulu to Diamond Head, and then much of the way back. By then the sun was setting, and we sat in the same spot for 20 minutes as the sun disappeared behind the horizon. Gaelyn took some really nice pictures of us ("it's my second job" 😆).
Written December 25, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
it was wonderful to have you on board and to share the love of sailing and ocean.
not to mention that beautiful sunset.
Stay safe and well and keep on enjoying your honeymoon mood!
With warm aloha,
Capt. Gaelyn
Written January 4, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
czar479
Denver, CO260 contributions
Mar 2022
Had the best time ever sailing with Captain Gaelyn on her lovely sailboat, Kaikiwi! My husband and I did a 3 hour sunset sail in honor of my birthday, and it was truly magical. The boat was immaculate, and Captain Gaelyn was prompt, professional, and extremely thoughtful and kind--allowing us the option to reschedule when the weather on the day of our initial booking was less than ideal. The way she is able to handle that boat on her own is beyond impressive. We are already budgeting for our next sailing adventure. Thank you, Captain Gaelyn! We can't wait to sail with you again!
Written March 22, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was a total pleasure to help you celebrate your birthday. Any occasion is a good one to be out on the water but what a highlight for you! Thank you for your kind words. I do look forward to sharing more ocean time with you and hubby.
Written March 23, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
S.G.
2 contributions
Apr 2023 • Couples
5 stars isn’t enough. I sailed with Captain Gaelyn a few years ago to see if sailing a larger boat off shore was for me. It was the perfect experience! You cannot find a more personable, professional, safety minded , dependable Captain in Hawaii. Long after she took us out she stayed in contact with me providing knowledge and advice during an unpleasant and costly boat purchase from Mexico. She did all of this with no financial benefit to herself. She kindly helped me get my boat to home port . She selflessly provided the sense of trust and encouragement needed for me , as an inexperienced sailor, to get my boat to home port. Words and star ratings on this app cannot fully express her excellence. If you’re ever in Hawaii and just want a great easy sunset sail, fire works sail, or whale watching cruise. She is the best choice. If you really want to take the helm and learn to sail, you can find no one better here to help you! My experience with her has been priceless and rating her at 5 stars diminishes how truly wonderful my experience with her was!
Written April 13, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Seeing someone passionate about the ocean and sailing, as you so clearly showed me, made it easy to step in and guide a little along your incredible path to boat ownership. Now YOU get to go sailing! Enjoy every moment, even those frustrating ones :-)
With warm aloha,
Capt. Gaelyn
Written April 30, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Tiffany M
Saint George, Utah, United States12 contributions
Sep 2022
Booking a private sailboat with Captain Gaeyln on the Kaikiwi, was the highlight of our trip to Oahu! There are several sailing excursions to choose from but you are packed on a catamaran with 50 other people, with load music. If you want to experience true sailing along the beautiful coastline with cobalt blue blue waters book with Captain Gaeyln, you will be blown away. Captain Gaeyln helped us customize our sailing trip and took us out for 7hs, so we could experience the trade winds and end our trip with a beautiful sunset.
Written September 16, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was a total pleasure having you on board. One might think 7 hours is too long to charter! If you have the right adventurous spirit and love of ocean, you may well find, like this couple did, that it is indeed the correct amount of time not to mention the highlight your HI vacation. What a way to refresh your spirit! Thank you for sailing with Sail Blue Hawaii.
Written September 16, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Raine S
2 contributions
May 2022 • Friends
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 got to enjoy our own drinks and snacks onboard as well. We would highly recommend sailing with Capt. Gaelyn, and we definitely look forward to our future sail together.
Written May 29, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was a tremendous sunset on such a grey day. Thank you for sharing your thoughts online and I do look forward to another sail together!
With warm aloha,
Capt. Gaelyn
Written May 31, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Misty F
Kaneohe, HI17 contributions
Jan 2021 • Friends
I cannot recommend this highly enough! Capt. Gaelyn was accommodating, friendly, and the consummate professional! Her boat was clean and clearly well cared for. Capt. Gaelyn helped us find her slip, and talked us through the process. Our overall time in the harbor was about 2 and a half hours, during which she sailed smoothly and skillfully. As she promised, it was a beautiful and relaxing evening. If you're looking for an intimate, tranquil way to experience an amazing Hawaiian sunset, look no further! Capt. Gaelyn is your best choice!
Written January 3, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
it was wonderful to have you on board to bring in the New Year while being so thankful and appreciative.
Do stay safe and well and I hope we sail together again.
With warm aloha,
Capt. Gaelyn
Written January 4, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Andrew B
1 contribution
Feb 2022
My wife and I went out for a 4-hour sail with Gaelyn and had a wonderful time. I'm an experienced sailor and the sailing itself was not that great. The trade winds decided to take a break that day and we were only getting winds of about 5 knts for most of our time. That's nothing that anyone can control and, at times like that, you have to remember a rule of the sea - "a guy in a motorboat is trying to get someplace, but a sailor is always right where he wants to be." All of this is to say, if you are cool with being out on magically blue waters, with Diamondhead for a backdrop, then you will likely have a good time regardless of the winds. Gaelyn is a superb skipper who really knows her tuff and she takes good care of her guests. The best part of our trip was the whales! February is the height of the whale season and we saw a lot! Being on a sailboat is one of the best ways to see whales. The boat doesn't make any noise when you're under sail, so we actually heard most of our whales before we saw them. We'd hear the sound of their breath coming up behind us. It was an extraordinary time.
Written March 14, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
I remember the day so clearly for its lack of wind lending to an exceptional whale watching afternoon. I was happy that you chose to enjoy what was given you...the perfect attitude for a day of sailboat chartering. Indeed, you were where you wanted to be. I so appreciate clients who appreciate...you make your trip, I don't.
Written March 23, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
jellene
Dallas, TX3 contributions
Oct 2021 • Couples
Gaelyn took 4 of us out on her beautiful sailboat to scatter ashes and watch sunset. She is so respectful, completely prepared and informative and timed everything so beautifully. We want to go again and just visit with her and celebrate Hawaii. Thank you Gaelyn for this unforgettable outing.
Written October 3, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was an honor to host your precious evening and take you sailing into the sunset after spending time remembering his life. Thank you for choosing and trusting Sail Blue Hawaii.
I hope your trip home has been easy.
I look forward to sailing with you again sometime.
Aloha,
Capt. Gaelyn
Written October 4, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
chris S
3 contributions
Aug 2022 • Couples
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.
Written August 14, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was a total pleasure having you on board. You did great for newbies!! Keep on learning and keep on sailing. I look forward to sharing a whale sail with you on February.
With warm aloha,
Capt. Gaelyn
Written August 14, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
D S
Dallas, TX19 contributions
Feb 2022 • Friends
CAPT. G is an awesome captain that has a wonderful sail boat. She wants you to have the best sailing experience possible. She honestly told me the day of my scheduled sail that there was little wind. She allowed a change to another day and a local seaman called her an honest captain as not all captains would do that! She is super knowledgeable and cares about all things important! She did a fantastic job of sailing the boat! A highlight if my entire trip to Oahu! We had the opportunity to see whales (whale season) dolphins and sea turtles! Class act!
Written March 19, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
It was terrific being on the water with you on such a placid day which is a perfect way to see the marine life.
Thank you for sharing your thoughts online
With warm aloha,
Capt. Gaelyn
Written March 19, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
What are your rates for private sails? How far in advance do we have to schedule? Thanks!
Written June 3, 2018
please respond to me though my direct email found on my website
mahalo
Written June 3, 2018
What are your rates for private sails? How far in advance do we have to schedule? Thanks!
Written June 3, 2018
Ahoy and thank you for your inquiry.
I would love to be a part of your Hawaii vacation and take you sailing.
rates depend on how many in your group.
the further in advance you broke the more likely you are to get your first choice
I look forward to spending Kaikiwi time with you.
With warm aloha,
Capt. Gaelyn
(808) 347-0235
Written June 3, 2018
Hi there, I'm coming to Honolulu this month on the 30th and leaving on the 5th. Im keen to either sail to Molokai and back again or if thats not available do some half day sailing. I have completed level 1 yachting in Australia.
Is any of that possible?
Sarah
Written September 22, 2017
Ahoy Sarah and thank you for your inquiry.
I would love to be a part of your Hawaii vacation and take you sailing. Molokai is part of a multi-day adventure and, unfortunately, I don't have availability for that due to current bookings. Very happy to take you for a day-sail tho.
Private sailing (you are not sharing the boat with another group) on "Kaikiwi", the 42 ft Beneteau 411 featured on my website, begins at
$ 429.77 for up to 2 1/2 hours; this price includes Hi State tax (.04712), boat and captain's fee. It is not a per person rate.
Longer sailing events are a very popular choice for most people:
$ 105 (plus tax) for each additional hour.
Because this is custom sailing, we can sail any time of day you want and whatever length of time you wish. Our islands are most consistently graced with trade winds so any time of day is a good time to go sailing...morning, afternoon, sunset. It is all good.
That being said, sunset cruising is all about kicking back and relaxing, perhaps enjoying a cocktail. I sail with a lighter sail plan than during the day unless otherwise requested.
"Kaikiwi" sails from Oahu's south (protected) shore, not far from Waikiki, past beautiful coastline in the cobalt blue blue waters of our Pacific. Wildlife such as green sea turtles, "honu", dolphins, "nai'a", humpback whales, "kohola" (in winter season only), and flying fish, "malolo" are some of the critters we may see as we sail. Beautiful views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen. Please understand this is not "destination" sailing. "Destination" is sailing.
Bring food and beverage for your day/evening on the water. Adult beverages are welcomed on board but, please, no red wine. (Unfortunately, due to liquor licensing laws in Hawaii, SBH is not authorized to supply alcohol for you.). Catering options are also available upon request.
To board and sail on Kaikiwi, all clients must be agile and mobile.
Because our exposed coastline is subject to currents (creating a high liability for the captain if swimming is even allowed), has no secluded coves/ lagoons and has unspectacular reef in our sailing area, snorkeling is not offered. While your private charter is primarily a sailing experience, if you would like a swim (you must be a strong swimmer), let me know and, after assessment of conditions, the captain can drop sail while you all jump in the water. We don’t anchor: we drift with the current and a floating tether is attached to the boat. This is a bunch more fun than being anchored. For safety reasons swimming is not an option during a sunset cruise.
Please call me with your credit card details to book your charter.
To help you make the most of your private sailing adventure, please let me know if you have any questions or concerns.
With warm aloha,
Capt Gaelyn
(808) 347-0235

Written September 22, 2017
Hello! We are going to Waikiki this June with our family members of 10 for our son's graduation trip. Kids ages 15-20….4 adults…..this sounds terrific….would teens be bored (ugh sigh how could they) and two how costly was it?
Thank you!!
Written April 20, 2015
Ahoy and thank you for your inquiry!
"KAIKIWI" has a US Coast Guard maximum of 6 passengers.
OR, the catamaran is available for sunset cruising @ $ 465 per hour for your 10.
Private sailing on "Kaikiwi", the 42 ft Beneteau 411 featured on my website begins at
$ 429.77 for up to 3 hours.
3-hour price includes Hi State tax (.04712), boat and captain's fee. It is not a per person rate.
Longer sailing events are a popular choice for most people:
$ 100 (plus tax) for each additional hour.
Because this is custom sailing, we can sail any time of day you want and whatever length of time you wish. Our islands are most consistently graced with trade winds so any time of day is a good time to go sailing...morning, afternoon, sunset. It is all good.
That being said, sunset cruising is all about kicking back and relaxing, perhaps enjoying a cocktail. To keep food on the table and the cocktail in your hand, I sail with a lighter sail plan than during the day.
If you want to throttle up and do some rail-in-the-water full-sail sailing, choose a day-sail (and, I promise, you can still enjoy your cocktail!)
"Kaikiwi" sails from Oahu's south (protected) shore, not far from Waikiki and includes sailing past beautiful coastline in the cobalt blue blue waters of our Pacific. Wildlife such as green sea turtles, "honu", dolphins, "nai'a", humpback whales, "kohola" (in winter season only), and flying fish, "malolo" are some of the critters we may see as we sail.
Bring food and beverage for your day/evening on the water. Adult beverages are welcomed on board but, please, no red wine.
To board and sail on Kaikiwi, all clients must be agile and mobile.
Because our coastline is subject to currents and has no secluded coves/ lagoons, if swimming, all must be strong swimmers and happens only if weather and ocean conditions are favorable; captain's call. Three-hour sunset cruises are not compatible with swimming due to late time of day. In other words, you must book a longer charter in order to have time to sail, be in the water with good light and watch the sun go down!
Please call me with your credit card details to book your charter.
To help you make the most of your private sailing adventure, please let me know if you have any questions or concerns.
With warm aloha,
Capt Gaelyn
(808) 347-0235
SailBlueHawaii
Let's go sailing!

"There is nothing, absolutely nothing, half so much worth doing as simply messing around in boats". Kenneth Grahame.
Written April 20, 2015
Do you give saing lessons for a family, couple adults & kids ages 13, 12 & 9?
Written March 10, 2015
yes I do.
Private sailing on "Kaikiwi", the 42 ft Beneteau 411 featured on my website begins at
$ 399 for up to 3 hours
and is
$ 100 for each additional hour
Price is subject to Hi State tax and harbor fee (.07712) and includes boat, sailing lesson and captain's fee. It is not a per person rate.
Because this is custom sailing, we can sail any time of day you want and whatever length of time you wish. Our islands are most consistently graced with trade winds so any time of day is a good time to go sailing...morning, afternoon, sunset. It is all good.
"Kaikiwi" sails from Oahu's south (protected) shore, not far from Waikiki and includes sailing past beautiful coastline in the cobalt blue blue waters of our Pacific. Wildlife such as green sea turtles, "honu", dolphins, "nai'a", humpback whales, "kohola" (in winter season only), and flying fish, "malolo" are some of the critters we may see as we sail.
Bring food and beverage for your day/evening on the water. Adult beverages are welcomed on board but, please, no red wine.
To board and sail on Kaikiwi, all clients must be agile and mobile.
Because our coastline is subject to currents and has no secluded coves/ lagoons, if swimming, all must be strong swimmers and happens only if weather and ocean conditions are favorable; captain's call. Three-hour sunset cruises are not compatible with swimming due to late time of day. In other words, you must book a longer charter in order to have time to sail, be in the water with good light and watch the sun go down!
Please call me with your credit card details to book your charter.
To help you make the most of your private sailing adventure, please let me know if you have any questions or concerns.
With warm aloha,
Capt Gaelyn
(808) 347-0235
"There is nothing, absolutely nothing, half so much worth doing as simply messing around in boats". Kenneth Grahame.
Written March 17, 2015
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