Let’s go Sailing in Hawaii

Sail Blue Hawaii on Oahu provides an unparalleled sailing experience, offering guests the chance to explore the island’s breathtaking coastlines and clear azure blue waters. Whether it’s a romantic sunset cruise, a private sunrise cruise, a tradewind sailing adventure, or a relaxing day-sail, Sail Blue Hawaii’s knowledgeable captain ensures a personalized and memorable journey across Oahu’s stunning seascape. Let’s go sailing in Hawaii !

What kind of vessel will we be sailing?

Your safety and comfort are our number one concern: our vessels meet all U.S. Coast Guard inspection requirements.

Kaikiwi is a 42-foot Beneteau 411 and a wonderful sailing machine for Hawaiian waters. She is well proven: Capt. Gaelyn sailed her home from Mexico with two crew and was delighted with the way she handled in all conditions.

Kaikiwi  is offered for day-sailing only (up to 6 passengers). Inter-island/ overnight charters are NOT currently offered. Larger vessels, for 7 + passengers, are also available for all DAY-sailing occasions and custom cruising. 

Kaikiwi  has lots of shade so time of day does not affect heat/ sun exposure. Sailing in summer months is very very comfortable even in the middle of the day.

DON’T DREAM YOUR LIFE, LIVE YOUR DREAM

I am surprised by the number of clients who come to me and say “I’ve always dreamed of sailing but never had the chance until now”. Or, “all my life I have wanted to learn how to sail. Thank you Sail Blue HI for introducing me to sailing by offering me a top-notch CUSTOMIZED sailing lesson. Wow. I want more”. A sailing lesson is a beautiful gift to give at birthdays or Christmas. It will be remembered for a life-time as a highlight. Gift certificates are available for any kind of sailing.

Let’s go sailing in Hawaii with Sail Blue Hawaii.

capt.gaelyn@sailbluehawaii.com; text: (808) 347-0235

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

Sail Hawaii’s Best at Sunrise

Any reason is a great one to get out of bed early and sail Hawaii’s best at sunrise. This is an experience you will remember forever: our Diamond Head sunrise Cruise. Greet the new day aboard your private sailboat “Kaikiwi“. This is not only a great photo opportunity but a beautiful time of day to sail : a special way to remember your vacation in Honolulu. Certainly not everyone is an early riser but the view of Diamond Head, the early sun’s effect on the water, the sounds of early morning wind in the sails…it is so well worth the effort. And the view of early morning Waikiki is Waikiki at its best!  (Yes, the best way to see Waikiki is from a distance:-), on your very own private sailing charter.

Oahu Sunrise Cruise

A sunrise sailing charter starts with a lighter gentle early morning wind. Morning is also the best time for a sailing lesson. We start with a lighter wind and build your lesson as the wind builds. Your sailing lesson will begin at 0800. Earlier if you prefer, esp if you have just flown in from the east coast. Yes, you could include sunrise with your private sailing lesson.

Any time, any reason…Sailing Hawaii’s best at sunrise will be your vacation highlight

You certainly won’t regret getting out of bed early!  Contact Sail Blue HI today to Sail Hawaii’s best at sunrise. 

astonishing sunrise a couple of weeks ago

Dreams come true in blue Hawaii. Don’t dream your life, let Sail Blue Hawaii help you live your dream.

Hawaii private sailing charter

Any occasion is a great one to get out sailing on Hawaiian waters to enjoy some relaxing and refreshing ocean time. Especially here in Hawaii. The air is balmy and year-round trade winds provide Honolulu with wonderful sailing conditions

Don’t dream your life, live your dream

Our most popular boat tours are certainly the private yacht charter, weddings, anniversaries and sunset sailing cruises. In addition, sailing lessons, birthdays and corporate adventures await.

While sailing in Honolulu we often see Hawaiian green sea turtles lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset.

SUNSET SERVED DAILY

Sailing Lessons, Learn the Ropes

sailing lessons in Honolulu

American Magic may be out, but the race to the America’s Cup continues. Whether you’re an avid Cup follower or just interested in sailing lessons to learn the ropes, this is one of the most exciting events in yachting.

Talking about “learning the ropes,” the first thing you learn in boating is that they are “lines”, not ropes. A rookie shows who s/he is because their ease (or lack of) with the nautical language will give them away in a heartbeat. And there is nothing wrong with being a rookie…we all start at the beginning. Boating, and especially sailing lessons, do indeed have its own language and it is learned over time by just being around sailors and being onboard. Sit back and listen and you can learn a lot through osmosis. Participate, ask questions, listen and learn and you will soon be talking this language too. What fun!

About the photo… You can understand from the way the docklines are tied what kind of boater each is. You can even sum up how they handle their boat and, perhaps, how “bristol” (shipshape) their boat is. Two different styles, indeed! I know whose boat I want to sail on.

Come on over to Sail Blue Hawaii for some Oahu sailing: sit back, relax, indulge yourself in a private sailing charter and the gift of “just being out there” and I bet you go home with some of that nautical language in your head, whether you want it there or not. 😉