A Perfect Hawaii Sailing Charter

You have just navigated your way to Sail Blue Hawaii LLC and your perfect Hawaii sailing charter. “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, famous Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen.

Talking about Navigation…

I was sailing with a family the other day and happened to mention that new boats are sold without a compass. Astounding, I know. They couldn’t believe it either. Well then, how the heck to you get from A to B? Everything today is electronic, from your charts to your navigation systems. Hence…no (“need for a”) compass. It’s like kids growing up and not knowing how to tie their shoe laces or even what a shoe lace is. In many ways, the young generations can be envied for what is at their fingertips. But it is very sad the day the compass dies, along with the paper chart (which cannot be purchased any more. If you really must have one, you have to special order it.) I love to have my hands and eyes all over paper charts. I love to use and teach with my compass. I am hanging on.

Kaikiwi’s compass can double as an inclinometer

A six-year-old, looking at my compass, asked if it is my “tip meter”. Sweet.

“The Riddle of the Compass”

is an intriguing book by Amir D. Aczel. The story of the compass is shrouded in mystery and myth, yet most will agree it begins around the time of the birth of Christ in ancient China. It is an historical and scientific exploration of the magnetic compass, arguing it was the single most transformative invention after the wheel. The book traces the device’s evolution from ancient Chinese divination tools to its revolutionary impact on global navigation, commerce, and the Age of Exploration. Have it read to you here: https://www.youtube.com/watch?v=Hvybyr-du5w or buy it from your local book store.

I found this to be a gripping read…truly.

How can you learn more about Sailing and Navigation et al, in real time?

Whether a sailing lesson or a casual private sailing charter, Sail Blue Hawaii can customise your special sailing request. It’s while sailing you can ask all questions…a far better way to learn than thru AI. AI is not even close.

Navigate your way to Sail Blue Hawaii LLC and your perfect Hawaii sailing charter.

5 BEST HONOLULU PRIVATE SAILING CHARTER IDEAS

Honolulu TRADEWIND sailing, where any time is a good time to be on the water. Highlight your Hawaii vacation aboard a sailboat on our beautiful cobalt blue Pacific Ocean. Here is our recommendation on SOME OF the MANY 5 best Honolulu private sailing charter ideas.

Private Sailing ideas; Waikiki, Hawaii

  1. A tradewind day-sail. 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 tradewinds so any time of day is a good time to go sailing…sunrise, morning, afternoon, or sunset. IT’S ALL GOOD!
  2. A sail to take in the beautiful views of Oahu and beyond. Outstanding views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen. This is not “destination” sailing.  “Destination” is sailing.
  3. A private day-sail to capture sightings of marine life. “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.  (I believe we did see a mermaid one time; sh sh sh……………)
  4. Birthday celebrations at sea. What better way to celebrate that special day for that special someone than aboard a private yacht charter in Honolulu?
  5. Corporate Events. Celebrate with the team onboard a sailing yacht off the Honolulu coast. How better to raise morale and reward them for a job well done?

Many many ideas for your custom cruise are accepted and sailed

https://youtube.com/shorts/PBDlY4_DZnA

https://youtube.com/shorts/PBDlY4_DZnA

This was one beautiful day to sail around Diamond Head into Maunalua Bay. My guests got the last good sailing in before Oahu was rocked by a decent winter storm. Not all Sou’Westers are bad 😎. We were lucky. What a peaceful time.

View other movies on Sail Blue Hawaii’s youtube channel

When should we book?

a rare view while on a HI day-sail:

Email with your idea for your Honolulu Private Sailing Charter sail. Your experience aboard may well be the highlight of your HI vacation

Locals too! Take a day off and let’s go sailing capt.gaelyn@sailbluehawaii.com

The Horizon is NO Limit

Hawaii Tradewind Sailing at its Best

Welcome aboard Sail Blue Hawaii to experience Hawaii tradewind sailing at its best. Leave the tour bus behind and experience something different and unique…it may well be the highlight of your Hawaii vacation.

Where do we sail to?

“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. This is not “destination” sailing.  “Destination” is sailing.

What if I have never been on a sail boat before?

The beauty of a private sailing charter is that the experience your little group has is customised (Kaikiwi is USCG certified for 1-6 passengers). You don’t need to have ever sailed before: I can tone it down or ramp it up to meet your group’s needs and expectations. Sailing outside Diamond Head is not for everyone. So, if your group decides so, we don’t go. It’s easy enough; just tell me who you all are… newby or a seasoned sailor, or part and part.

Email capt.gaelyn@sailbluehawaii.com today to book your Hawaii tradewind sail. The beauty and quiet of your private sailing charter may well amaze you.

View other movies on Sail Blue Hawaii’s YouTube channel !

Hawaii Ash Scattering

As captain of your private sail boat, I am honoured to help facilitate your Hawaii ash scattering/ life celebration at sea.

Your ash scattering includes a private sailing charter 

A reflective sail to Diamond Head establishes the mood for your ash scattering/ life celebration. How often are we surrounded by rainbows during this boat tour? Almost always. Talk about setting the mood!

Take as long as you need to talk about your loved one as you scatter their ashes and celebrate their life. Bring as many un-strung flowers/petals as you want. When all is done, an easy down-wind sail brings you back to the harbour.

When is the best time to sail?

Anytime is good…sunrise, sunset, morning, afternoon..you choose.


I hope your days here in Hawaii have lots of sunshine and brightness to them.
Hawaii is such a healing place…immerse yourself in that richness while here, and take it with you when you leave.

Choose Sail Blue Hawaii for your Hawaii ash scattering/ life celebration.

(turn on your sound)

Hawaii’s BEST Tradewind Sailing

Sai! Blue Hawaii offers a full range of sailing options; from casual sightseeing boat tours to special occasions (weddings, proposals at sea) to Hawaii’s BEST tradewind sailing. Whether you have never stepped foot on a sailboat before (exciting first time !!) or you are an old salt, your private sailing charter is catered to you. (Visit the “Let’s go Sailing” page for ideas.)

Where do we sail to?

“Kaikiwi” sails from Oahu’s (protected) south shore, near 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. We do look for mermaids too. The first to see one gets a free boat ride. 🙂
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.

Whoever needs to arrive to be happy?

Where in the world are you going to get this kind of tradewind sailing? Only here in Hawaii ! Sai! Blue Hawaii offers Hawaii’s BEST tradewind sailing daily on your vey own private sailing charter. Other companies may pop a little sail out but mostly motor-sail. Sai! Blue Hawaii offers REAL sailing. Who needs a theme park when you can do this for real? Remember, gentle sailing is offered too! The range is limitless. Just voice your pick.

DON’T DREAM YOUR LIFE: LIVE YOUR DREAM