Oahu’s Best Private Sailing Charter

When is the best time to book a private sailing charter on Oahu? 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. 

Will we see marine life on our private sailing charter?

Because Hawaii’s waters are relatively warm, this means our waters can be sparse in terms of wild life. Not to be disappointed though, on your private sailing charter, you may well encounter at least 3 types of marine life: turtles, dolphins and flying fish. “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.

Call Sail Blue Hawaii now for your private sailing charter.

A Hawaii Proposal

Hawaii is a place full of romance. You will feel it the minute you get off the plane…the balmy tradewind, the scent of plumeria in the air. So, what better place on the planet than Hawaii for your proposal of a lifetime.

Hawaii Proposal at sea

You cannot get any more romantic when you propose to your loved one while sailing into the sunset. Saying “YES” under a tropical sky, on your own private yacht, will be a memory of a lifetime. Of course, you don’t need the sunset to complete your proposal: 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.

I have sailed many a couple to witness their Hawaii proposal and every single one gives me chicken skin. It is an honour. Call Sail Blue Hawaii to book your Hawaii proposal at sea.

Ash Scattering/ Life Celebration in Hawaii

It’s easy to understand why you would want to celebrate your loved one on a private yacht on the blue Pacific waters off Oahu. Hawaii has a strong spiritual energy both on and off the ocean. A farewell at sea is a healing and soothing way to say goodbye and begin anew.

Customise your Hawaii Ash Scattering.

If you would like to include your pastor, or other, to conduct a service and/or blessing for you, please do. If you have no connections here, reach out and we can give you some suggestions. Perhaps you’d like to sail longer than just the time it takes to celebrate and scatter. What time of day is best? 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. 

Email us today with your Hawaii Ash Scattering request.

The Best Private Sailing Charter 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. 

Book a Waikiki private sunrise cruise

Maybe you’ve just flown in from the East Coast and Waikiki doesn’t wake up early enough for you. Let’s go sailing and catch sunrise over Diamond Head. It is possible that we’ll see dolphins in the beautiful morning light. Bring your favourite coffee and muffin. It’s so exciting to board in the pre-dawn hours and head out the channel in the dark. The anticipation of sunrise is palpable. Imagine, your own private sailboat, ON YOUR FIRST DAY OF VACATION, sailing towards one of the most famous landmarks on the planet, Diamond Head! It is exciting, thrilling, magical. AND this could be YOU!

The best way to start the day

Before you leave home, call Sail Blue Hawaii for a private sailing charter. Did you forget to do that and you are already on island? Give Sail Blue Hawaii a call and hope the sunrise cruise is still available. You will not be disappointed.

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