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

Say “YES”…Hawaii’s best private proposal at sea

The Hawaiian islands are known for their romance. So, what could be more perfect than saying “YES” aboard your own private yacht at sunrise or sunset? YES, trust Sail Blue Hawaii…Hawaii’s best proposal at sea …with this incredibly important event. Sailing this romantic Hawaii marriage proposal will guarantee she says “yes.”

Saying “yes” is just the beginning

May the love you share today be just as strong every day in all the years to come. You will look back on this day as not just the highlight of your Hawaii vacation, but the highlight of your lives. Your private Hawaii marriage proposal at sea will set the tone for your lives together as you sail off into the pacific’s incredible sunrise or sunset.

video by Dro Gregorian: Proto-Pilot.com.

Trust Sail Blue Hawaii LLC, Hawaii’s best private proposal cruise, with your Hawaii proposal while sailing on your own private yacht. Romance, baby!

Hawaii sunset fireworks cruise

HAPPY BIRTHDAY AMERICA! Every Friday evening off of Waikiki we have a very awesome fireworks event. Sail with Sail Blue Hawaii and experience your very own romantic sunset cruise followed by fireworks.

5 great reasons to choose a sunset fireworks cruise in Hawaii

  1. Celebrate a birthday. Nothing could be more special than to see the sun going down followed by fireworks while you are sailing your birthday cruise.
  2. Propose to your intimate other. If you want to wow him/her with a moment to last a lifetime, choose the sunset. Add to that, the city lights, and you have a moment that will last a lifetime. How can they possibly say anything but “YES!”
  3. Say “I DO”! What could be more romantic than having your wedding at sea. After your nuptials, the captain will sail you into the sunset. Do this on a Friday and stay out longer to watch the fireworks.
  4. Full moon cruise. Enjoy a full moon/ sunset/ city lights/fireworks cruise in Honolulu. It will be unforgettable.
  5. You don’t need a reason to sail a sunset fireworks cruise while in Hawaii. Just be there and the spectacular moments will be with you forever.

Give Sail Blue Hawaii a call and book your sailing charter now. Your sunset fireworks cruise will be the highlight of your Hawaii vacation.

5 top full moon/ sunset cruise ideas

A sail to remember for a lifetime is our sunset/ full moon cruise. There are so many reasons to get out on the water at this time of day. This could well be the highlight of your Hawaii vacation.

Honolulu full moon/sunset cruise..5 best reasons

  1. Celebrate a birthday. Nothing could be more special than to see the sun going down and the moon rising while you are sailing your birthday cruise.
  2. Propose to your intimate other. If you want to wow him/her with a moment to last a lifetime, choose the sunset/full moon cruise. Add to that the city lights and you have a moment that will last a lifetime. How can they possibly say anything but “YES!”
  3. Say “I DO”! What could be more romantic than having your wedding at sea. After your nuptials, the captain will sail you into the sunset. Take in the moment, then turn around to see the full moon rising over Diamond Head.
  4. Blue moon cruise. “Once in a blue moon”. What does that even mean? On an occasional month, (because the moon’s month is shorter than earth’s), the moon is full twice in one month. Enjoy a blue moon/ sunset/ city lights cruise in Honolulu. It will be unforgettable.
  5. You don’t need a reason to sail a sunset/full moon cruise. Just be there and the spectacular moments will be with you forever.

Give Sail Blue Hawaii a call and book your sailing charter now. Your full moon cruise/sunset cruise will be the highlight of your Hawaii vacation.

Hawaii Proposal at Sea

Definition of romance: chartering your private yacht to propose to your loved one while in Hawaii. Imagine saying “YES” while sailing into the sunset.

Sail Sunset on Valentine’s Day

This Valentine’s Day was a highlight for me. I have been running private charters for many years now but this one stands out. The young couple, delighted in each other, chose to spend their time on the forward deck…what I call the “best seat in the house”. Not long into our sunset sail, a whale breeched, some distance from us but still out-of-this-world spectacular. We spent the two hours enjoying 2 whale groups as they swam and played in Mamala Bay. Honolulu, Hawaii. Humpback whale sighting rules are strict here: keep a minimum 100 yard distance and do not change direction to follow them. No worries! We just sailed our track and the whales theirs and the show went on. The couple I took sailing earlier in the day have been thrilled daily by whale sightings from their Waikiki lanai. But there is NOTHING better than seeing them from your Hawaii private yacht.

Dolphins too!

Yep. As if the humpbacks weren’t thrilling enough, the Hawaiian spinner dolphins came out to play. Usually in my sailing area, dolphins cruise by around 10 in the morning. So imagine the thrill of this huge pod swimming in Kaikiwi’s bow wake, frolicking and spinning all around us. WOW! As sunset came on, he asked, she said “YES”! How could you not after a show like this?

Sail Blue Hawaii

Call today for your Hawaii proposal at sea. It will stay with you for your lifetime.