Hawaii Private Sailing Lesson

Sailing is clouded in romance. Many people dream of a life of sailing and the adventure of perhaps one day sailing to distant shores. The reality is often different than the dream and this is important to understand.

So, before you go buy that boat, come sailing with me and begin or continue learning the skills that will gain you confidence and give you a whole bunch of joy as you succeed. Your time “out there” with me will also give you a taste of what true blue-water sailing is all about.

You don’t have to have the dream of distant shores to sign up for a lesson…you can begin by taking up sailing as a day-hobby.

Don’t dream your life, live your dream

Do you have someone in your life who has always had an itch to try sailing but has never had the opportunity? Buy him/her a gift certificate for a private sailing lesson. It will be the best present they have ever had!

Whatever your goal is, the lesson will fit.

Even if you are the only one who wants to learn and you don’t wish to come alone, your friends/ family are welcome on board and can enjoy the sail while you learn.

So, whether your dream is to sail the Waikiki coast or beyond that horizon, your personalized lesson is waiting for you!

This could be you at the wheel.

Call Sail Blue Hawaii today for your Hawaii private sailing lesson.

Honolulu Private Yacht, Private Sailing Charter

In your google search for a private yacht or private sailing charter in Hawaii, SOOOO many listings come up. It is overwhelming. How do you choose the perfect yacht for you and your sailing needs? Who do you choose for your Hawaii private sailing charter. Can you trust the websites you find?

Don’t dream your life; LIVE your DREAM

While in Hawaii, what can be more perfect than getting out on the water to unwind. The wind in your sails gifts you an incredible ride on our beautiful Pacific waters. But who do you choose for this most special experience? Don’t be overwhelmed with the choices out there. Sail Blue Hawaii is Hawaii’s premiere charter company. There is a reason people choose Sail Blue Hawaii. This trusted company has been around for years.

Your safety and comfort are our number one concern: our vessels meet all U.S. Coast Guard inspection requirements.

Whether you are a group celebrating a special occasion, or a solo sailor, we have the perfect sailing yacht for you. Whether it’s a romantic sunset cruise for two, a sailing lesson, or a laid-back blue water sail, we have the perfect occasion for you.

Kaikiwi, a 42-foot Beneteau 411, is a wonderful sailing machine for Hawaiian waters. She is well-proven.  Capt. Gaelyn sailed her home from Mexico, with two crew, and was delighted with the way she handled in all conditions.

You can book Kaikiwi for day-sailing (up to 6 passengers). Or choose larger vessels for your party of 7 to 35. With Sail Blue Hawaii you book with confidence, knowing that you are well cared for. Get ready for the highlight of your Hawaii vacation on your private yacht, sailing a private charter.

Honolulu’s Best Private Sailing Charter

Sail Blue Hawaii has been blessed with many wonderful reviews proving it to be the best Honolulu private sailing charter. Recently I took a family on a day-sail. It was the first day of their Hawaii vacation. “Everything after this is going to be boring” a family member said in the middle of a brilliant day of sailing. I certainly hope the rest of their vacation was not boring, and I am sure it wasn’t, but I did love the comment.

Enjoy a private sailing charter while on Oahu

Here are some of the comments after a private sailing charter with Sail Blue Hawaii:

“This is the best time I have had in my entire life.”
-Kaelyn, age 7, CA

“Thanks for a relaxing few hours. Everything was perfect;  the wind, the weather, the seas, the boat and, of course, the skipper. The girls said that only a woman could have a boat looking so good!
We appreciated being part of your crew and hope we can do so again on our next visit to these beautiful islands.”
-David, Gillian and Leanne – Brisbane, Australia

“We would like to thank you for your help and commend you on your professionalism in planning our cruise. You have helped to make our wedding a memorable event for
both our guests and ourselves.”
-Kreg and Marjorie, Canada

“We couldn’t believe our eyes when we saw the mama and baby whale gently arching out of the water alongside the boat.”
-Virginia, Kauai

“Captain Gaelyn, we just wanted to drop you a little note thanking you again for such a wonderful time last Thursday night.  The cruise was wonderful and more than we had hoped for.  It was really nice to get out and be a couple for a little while, instead of just mommy and daddy. Thank you again!!”
-Mike and Robin, Honolulu

“Our sunset sail with Captain Gaelyn was the highlight of our trip to Honolulu. She and her friendly crew took great care of us. We had a terrific time and will enjoy our memories of the sail.”
-Kelly Rouse, CA

“ We were sailing after dark with the twinkling lights of Waikiki and Honolulu on the skyline thinking it couldn’t get any better when a gorgeous and huge fireworks display lit up the sky.
Capt. Gaelyn said it was a “little surprise”
she had arranged just for us.”
-Candace, Kauai

“As usual, I had a totally wonderful time on the ocean with you.  The whales were so cooperative, and the water was SO INCREDIBLY BLUE!!!!  Ku called it cobalt.  Mahalo nui loa for yet another absolutely beautiful and unforgettable experience!!”
-Mak, Honolulu

“Our group had so much fun on the whale cruise yesterday, Gaelyn! There were some pretty amazing photos too…Thank you, Captain Gaelyn, for a fantastic day on the boat with you. All the whales were so amazing and our whole group of yoga teacher trainees was excited about seeing them.  I felt completely relaxed and safe in your hands. I can’t wait to go again!”
-Rupali, Yoga Hawaii, Honolulu

“We will never forget the absolute magic and perfection of our wedding aboard your sailboat.  Your warm and friendly welcome made us feel immediately at ease and at home . We loved sailing into the sunset and exchanging our vows with our loved ones looking on.  Thanks for being our captain and our wedding celebrant. Our time with you was peaceful and joyful. Thanks for the cherished memories.  Wishing you the very best always.”
-C & V, Hawaii

Many, many thanks for a lovely day.  It was perfect: lovely boat, great sun and wind, and how you managed to arrange for the dolphin show is beyond me.  Great day!”
-Fredda, Waimanalo

The family of Mort Brown joins all of us here in extending our thanks to you  for doing such a terrific job last week. Your thoughtful, sensitive handling of our memorial cruise was very much appreciated. It did all of our hearts good to be able to say goodbye to a dear friend and colleague
in such a meaningful and graceful way.”
-Valerie Yee
Vice President & Asst. General Manager
Hawaii Public Radio 

” So fabulous!! I can still feel the ocean wind on my face, hear the slow sea splash against your beautiful sail boat and your gentle sailing touch, Capt Gaelyn. Thank you for such a special evening.”

– Arlei, Honolulu

“You certainly gave us such a wonderful gift of a relaxing sail; which in turn brings back memories of previous sails and, as always such a panoramic view of our beautiful city and Diamond Head.”

– George, New Mexico

“This is the best evening I have had in many years. I feel rejuvenated.”
-Nancy, Honolulu.

“It was sheer joy! Everything was perfect;  the water, the sky, the wind, the fish and the dolphins!!
What a way to end our stay in Hawaii!
Capt Gaelyn, your love of the water made it extra special.”

-Harold & Sheryl, Houston, TX


“part of hidden Hawaii”
“off the beaten track”
“I have never felt so alive”
“memory of a lifetime”
“one of Hawaii’s secret jewels”

“Captain Gaelyn, sailing with you was the highlight of our Hawaiian vacation.”
-more people than I have room to list

Kaikiwi at rest

Sign up for your Hawaii sailing adventure today with Honolulu’s best private sailing charter

Hawaii’s BEST Private Sailing Charter

Any occasion is a great one to get out sailing on the Hawaiian waters to enjoy some relaxing and refreshing ocean time. Especially true here in Hawaii where the air is balmy and year-round trade winds provide Honolulu with wonderful sailing conditions.

“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”

Our most popular boat tours are the private yacht charter, weddings, anniversaries and sunset sailing cruises. In addition, sailing lessons, birthdays, corporate events, custom adventures await.

While sailing in Honolulu we often see Hawaiian green sea turtles lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset.

Call Sail Blue Hawaii to day for your Hawaii private sailing charter. It could well be the highlight of your Hawaii vacation.

5 best Hawaii private sailing charter ideas

  • You want to treat your family to a private boat tour while vacationing in Hawaii. How better than to choose a private sailing charter to keep your family safe and Covid-free. Not to mention experiencing the pure joy of sailing‼
  • At sea, on your Hawaii private sailing charter, you find a different and very unique way to see the island of Oahu. Sometimes “the best way to see Waikiki is from a distance”. Clients always chuckle and agree!!. Sit back, relax and take in the beautiful views of Oahu and Diamond Head. On clear days, far in the distance, you can see Molokai and Lanai. 

You can’t bring your boat with you on vacation

  • You have a sailboat back home. It’s so frustrating to sit on the beach and watch the boats go sailing by. Your Hawaii private sailing charter with Sail Blue Hawaii will blow that frustration away and give you the supreme tradewind sail that only Hawaii can offer. 
  • You have a boat back home but have never stepped aboard a sailboat! Now is your opportunity to have the experience you’ve always wanted. With an experienced and local-knowledge-savy skipper you can sit back and relax without the annoying sounds or smells of your back-home power boat. You might finally understand the reason why sailing is not about a destination”.  “Destination” is sailing. You might even get hooked!
  • Because this is custom sailing, you 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…✨SUNRISE, morning, afternoon, SUNSET.✨  It is all good. 
Yet another day of fabulous sailing from Mexico to Honolulu. Kaikiwi.