Hawaii’s Best Private Sailing Charter

When you book Hawaii’s best private sailing charter, it may well be the highlight of your HI vacation (locals invited too!!). It is truly 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 provide the best private sailing charter experience. That was my goal when I set up up Sail Blue Hawaii LLC, and bought my beloved “Kaikiwi”.

“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 beautiful 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, NOW!, 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.
  • perhaps you’ve just flown in from the East Coast and Waikiki doesn’t wake up early enough for you. Let’s catch an exceptional time of day: 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 at sea:  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

Choose an adventurous day-sail as the photo suggests, or a gentle sail…the whole spectrum is available, any time of day, any length of time. Just communicate your wish when you email

Sail Blue Hawaii

your choice for Hawaii’s best sailing charter. We are the only charter company who REALLY SAILS!!.

Don’t dream your life, live your dream

Waikiki Sailing at its BEST!

Private boat tours in Waikiki are available with Sail Blue Hawaii. Weekends and holidays fill quickly so plan ahead and book today. Your experienced captain will ensure your safety and enjoyment. The cost of a private boat tour in Waikiki is affordable and highly desired. Your private yacht is spacious, featuring covered and open air seating as well as an onboard restroom.

Dreams come true in BLUE 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 cruise, tradewind day-sail, SUNSET cruise✨.  It is all good. A client this week was concerned if we left at 0800 for a 3-hour sail we wouldn’t have enough wind. So much sailing, anywhere in the world, relies on an afternoon sea breeze. The fact is, we rely on tradewinds and not sea/land breezes. This makes Hawaii sailing unique and desirable, ANY TIME OF DAY. His concern was also the mid-day heat. “Kaikiwi” has lots of shade, so, time of day does not affect heat/ sun exposure.

Don’t dream your life, live your dream

Private Waikiki boat tours with Sail Blue Hawaii are for both tourists and locals looking to rent a private boat. Tradewind sailing, sunset cruising, coastline sightseeing and Friday night fireworks are among the most popular tours in Waikiki. Birthday and life memorials are also very popular. We accommodate a wide range of special events aboard. The Horizon is no limit.

So, give Sail Blue Hawaii a call for your own private boat tour in Waikiki.

Scattering ashes at Sea in Hawaii

Hawaii has a strong spiritual energy both on and off the ocean so it is no surprise that a farewell at sea is a healing and soothing way to help say goodbye and help you to have strength as you begin this life change.

Call Sail Blue Hawaii for your custom ash scattering at sea.  Let us know about your loved one and how you want to celebrate their life.

What time of day should we sail?

A gentle sunrise cruise is popular. A great way to greet your new day and celebrate your loved one. “Kaikiwi” has lots of shade so time of day does not affect heat/ sun exposure.
So, a day-sail is also a good choice. Sunset cruising is very popular. All are options for your private Hawaii ash scattering. Remember your loved one as your captain sails your private sail boat upon Oahu’s stunning azure waters. Take your time, there is no rush.

Gone from my sight.

 “I am standing upon the seashore. A ship spreads her white sails to the morning breeze and starts for the blue ocean. 

She is an object of beauty and strength. I stand and watch her until at length she hangs like a speck of white cloud just where the sea and sky come to mingle with each other.

Then, someone at my side says: “There, she is gone!”

“Gone where?”
Gone from my sight. That is all.  She is just as large in mast and hull and spar as she was when she left my side and she is just as able to bear her load of living freight to her destined port. Her diminished size is in me, not in her.

And just at the moment when someone says, “There, she is gone!” there are other eyes watching her approach and other voices ready to take up the glad shout:
“Here she comes!”
And that is dying.

– Henry Van Dyke, a 19th Century clergyman, educator, poet, and religious writer

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Call Sail Blue Hawaii to schedule your private Hawaii ash scattering, life celebration at sea.

Hawaii Ash Scattering

Hawaii has a strong spiritual energy both on and off the ocean so it is no surprise that a farewell at sea is a healing and soothing way to help say goodbye and help you to have strength as you begin this change.

Call for your custom ash scattering at sea.  Let us know about your loved one and how you want to celebrate their life.

When should we sail?

A gentle sunrise cruise, a day-sail, an awesome sunset cruise. All are options for your private Hawaii ash scattering. Remember your loved one as your captain sails your private sail boat upon Oahu’s stunning azure waters. Take your time, there is no rush.

Gone from my Sight

 “I am standing upon the seashore. A ship spreads her white sails to the morning breeze and starts for the blue ocean. 

She is an object of beauty and strength. I stand and watch her until at length she hangs like a speck of white cloud just where the sea and sky come to mingle with each other.

Then, someone at my side says: “There, she is gone!”

“Gone where?”
Gone from my sight. That is all.  She is just as large in mast and hull and spar as she was when she left my side and she is just as able to bear her load of living freight to her destined port. Her diminished size is in me, not in her.

And just at the moment when someone says, “There, she is gone!” there are other eyes watching her approach and other voices ready to take up the glad shout:
“Here she comes!”
And that is dying.

– Henry Van Dyke, a 19th Century clergyman, educator, poet, and religious writer

This image has an empty alt attribute; its file name is view-forward-with-rainbow.jpg

Call Sail Blue Hawaii to schedule your private Hawaii ash scattering, life celebration.

Let’s Go Sailing Oahu

Kaikiwi sails from Oahu’s south shore. You will embark at Kewalo Basin boat harbor, not far from Waikiki beach hotels. We sail past beautiful coastline in the cobalt blue blue waters of our Pacific. The south shore is the protected side of Oahu: calm and crystal clear, making it the perfect sailing destination.

Why go sailing Oahu

Common marine wildlife sightings on Oahu are for example, Hawaiian green sea turtles, honu, dolphins, nai’a, and humpback whales, kohola (in winter season only). In addition, flying fish, malolo are some of the critters we may see as we sail about the island. Sunrise cruise, day-sail, sunset cruise, private sailing lessons, ash scattering..are all available. This is custom cruising at it’s best.

Incredible sights while sailing

Beautiful breathtaking views of Diamond Head are just one of the highlights while sailing in Oahu. On clear days, although far in the distance, Molokai and Lanai can sometimes be seen from the island of Oahu. This is not destination sailing, destination is sailing!

While Kaikiwi is a US documented vessel she does like to fly the kiwi flag. All nationalities invited to sail!:

Email Sail Blue Hawaii today for your custom cruise. Let’s go sailing Oahu!