Private Sailing Charter in Hawaii.

When you book your private sailing charter while vacationing in Hawaii it may well be the highlight of your vacation. It is astonishing how many times my clients have said that to me. That is thrilling. It is exactly why I have worked so hard to give people the best-kept charter vessel in the islands, AND the best private sailing charter experience. That was my goal when I set up up Sail Blue Hawaii LLC.

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

Why choose a private sailing charter?

There are so many reasons, but let me name a few:

  • CoVid is still around. Your captain is vaccinated and boosted. How better to keep you and your loved ones safe. When you sail on “Kaikiwi”, a 42-ft Beneteau, you will feel so safe especially when you see the over-crowded catamarans.
  • delight in pure trade wind sailing any time of day for as many hours as you want.
  • whale sail. In winter, humpbacks are Hawaii’s most famous tourists, making their annual 3,500 mile trip from Alaska to the islands each December through April.  We’ll set sail and hope to find these gentle leviathans.
  • birthday parties
  • corporate fun(ctions)
  • very popular: summer only; Friday night pau hana fireworks cruise. Combine this with sunset and you have the perfect cruise.
  • for romantics: sunset cruise: a beautiful time of day to be on the water.
  • maybe you’ve just flown in from the East Coast and Waikiki doesn’t wake up early enough for you. Let’s catch sunrise over Diamond Head. Maybe we’ll see dolphins in the beautiful morning light.
  • choose the one night of the month (or, the “blue moon” second night of the month) to sail from sunset to full moon. It is truly magical to see the full moon rise over Diamond Head after sailing into the sunset. Click moon phases to see full moon calendar.
  • when the moon is close to its new phase, we have fabulous star-gazing.  Set sail for sunset and a night sail. In winter months, the iconic Southern Cross can be seen.
  • proposal:  how more romantic can you get when you propose to your loved one while sailing into the sunset?
  • weddings for romantics:  there’s nothing more special than saying “I do” under a tropical sky  while sailing into the sunset.  Your captain will marry you with a personalized  service on your own private yacht.
  • renewal of vows:  what a “wow” it is to  say those vows again, to remember and  re-ignite!
  • sailing lessonsHelp set the sails and take the helm if you like as you learn the “ropes” of sailing.  The first thing you learn: they are not ropes.  They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. For all levels of sailing experience.
  • memorials, ash scatterings and life celebrations
perfect tradewind sailing

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.

Hawaii’s Best Sunset Cruise

Any occasion is a great one to get out sailing on our 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. Sail Blue Hawaii offers private sailing charters, 365/24/7.

Combine your sunset cruise with fireworks

Why?

  • A surprise sunset sail for your loved one only gets better when you plan to include our weekly fireworks display off Waikiki.
  • A proposal at sunset culminating in the best of fireworks displays is a romantic and incredible way to begin a life together.
  • Say “I do”. Sail into the sunset after exchanging your wedding vows and finish your evening with a blast of fireworks.
  • Renew your wedding vows. What a romantic way to celebrate that best day of your lives. What could be better than a sunset/fireworks cruise?
  • A sunset cruise combined with fireworks is ideal for families too. It’s a thrill for all.
  • No need for a reason. A sunset sail/fireworks cruise will be the highlight of your Hawaii vacation.

Book today for Hawaii’s best sunset cruise with Sail Blue Hawaii. You will not be disappointed.

Hawaii’s Best Private Sailing Charter

This week has been a treat for gifting Hawaii’s best private sailing charter. Locals and tourists, both, signed up their loved ones with Sail Blue Hawaii for a surprise private sailing charter. In just two days I had three surprise birthday celebrations onboard.

When is a good time to go sailing in Hawaii?

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 is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET. ✨ It is all good. 

Why sign up for a private sailing charter in Hawaii?

Any reason at all is a good reason to sign up for a private sailing charter. Feel free to create your own custom cruise.  We will cater to your every whim.  Call us for your special occasion and we will design the sailing adventure of your dreams.

Do you have someone special in your life and just can’t find the right way to say “thank you” or “happy birthday” “happy anniversary” “happy Mother’s/ Father’s Day” ?  Stun them with a GIFT CERTIFICATE.  It could well be the best gift they have ever received.