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

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!

Honolulu Life Celebration

Sail Blue Hawaii is deeply honoured to help facilitate your special time of life celebration and aloha. It’s not an easy losing a loved one but being out on the beautiful Pacific Ocean is restorative and healing.

Ash Scattering at sea off Oahu

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 I can give you some suggestions. Perhaps you’d like to sail longer than just the time it takes to celebrate and scatter. You are welcome to an extended cruise. 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…✨a SUNRISE cruise, morning sailing, afternoon sailing, a SUNSET cruise✨.  It is all good. 

Call Sail Blue Hawaii today with your Hawaii Ash Scattering/ life celebration request.

Honolulu Sunset Cruise

Honolulu sunset sailing

Honolulu sunset sailing… a beautiful time of day to be on the water. What can be more romantic than sunsets aboard a sailboat in the pacific ocean. This a tour is something you’ll want to experience on your vacation in Honolulu. Here is our recommendation on the 5 best Honolulu sunset sailing ideas.

Sunset Sail in Honolulu Hawaii

  1. Friday night fireworks in Honolulu. This is the most popular and something everyone enjoys while on vacation in Honolulu.
  2. Birthday celebrations at sea. What better way to celebrate that special day than aboard a private yacht charter in Honolulu?
  3. Wedding and Engagement. Something truly unique, a way to make this day special. Several party planners in Honolulu highly recommend our services to guests visiting Hawaii.
  4. Corporate Events. Celebrate with the team onboard a luxury sailing yacht in Honolulu. How better to raise moral and reward them for a job well done?
  5. Hawaii Ash Scatterings and Memorial Services. Celebrate that special person in your life. We realize that it’s a very difficult time losing a loved one and we are here to help.

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.