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 lessons: Help 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

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

November 17, 2024November 17, 2024

Sail Hawaii’s Best Charter Boat, “Kaikiwi”.

Private Sailing Charters

Oh !! the luxury and awe of sailing your own private yacht in Hawaii. Sail Hawaii’s best charter boat,”Kaikiwi”, the best-kept charter boat in the islands. She is a US Coast Guard approved vessel, perfect for any kind of Hawaii sailing. Whether it’s an intimate sunset sail for two, an adventurous day-sail with family and friends, whale watching, entertaining business colleagues, watching sunrise over Diamond Head, saying “I do” under a full moon…the reasons to go sailing on “Kaikiwi” are endless and the experience will most probably be the highlight of your Hawaii vacation.

When is the best time to go sailing 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 of day is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET.✨ It is all good.

“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.

What does “Kaikiwi” mean?

“Kai” in Hawaiian means “salt water”; “kiwi”… enough said (unless you are unfamiliar with the global nickname for a New Zealander). “Salt water kiwi” perfectly sums up the captain and her beloved 42-ft Beneteau :-).

Don’t Dream your Life, Live your Dream

Sail Blue Hawaii on Oahu provides an unparalleled sailing experience, offering guests the chance to explore the island’s breathtaking coastlines and clear blue waters. Captain Gaelyn, their knowledgeable captain, ensures a personalized and memorable sail across Oahu’s stunning seascape. Email Sail Blue Hawaii to sail on Hawaii’s best charter boat, “Kaikiwi”.

November 3, 2024November 3, 2024

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.

June 9, 2024

Learn to sail in Hawaii

Whether you’re an avid sailor wishing to hone your skills or a newbie, you can learn to sail in Hawaii. Hawaii waters have some of the best sailing conditions on the planet. Learn the ropes with Sail Blue Hawaii and discover the excitement of 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 during sailing lessons, does indeed have its own language. This language is learned over time by just being around sailors and by 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!

Honolulu Sailing Lessons

Sail Blue Hawaii specialises in Private Sailing Tours on Oahu and offers all popular boat charters (sunrise cruise, day-sailing, sunset sail) and sailing instruction in Honolulu. Before you go buy that sailboat, come sail with me! Whether you are a beginner or need continued instruction, you’ll learn the important skills to gain confidence in Hawaiian waters.

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.

So, if your dream is to sail the Waikiki coast or beyond, your personalized lesson is waiting for you! Learn to sail in Hawaii

May 12, 2024

Honolulu’s 5 best private sailing charter ideas.

Honolulu’s best private sailing charter, where any time is a good time to be on the water. Highlight your Hawaii vacation aboard a sailboat in the pacific ocean.

A tradewind sail. 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 tradewinds so any time of day is a good time to go sailing…sunrise, morning, afternoon, or sunset! IT”S ALL GOOD!
A private sailing charter will take in the beautiful views of Oahu and beyond. Beautiful views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen. This is not “destination” sailing. “Destination” is sailing.

What will we see on our private Hawaii sailing charter?

3. A private day-sail captures sightings of marine life. “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.

4. Birthday celebrations at sea. What better way to celebrate that special day than aboard a private yacht charter in Honolulu?

5. 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?

perfect tradewind sailing

Sail Blue Hawaii caters to all: sailor or newbie. A private Honolulu sailing charter will be the highlight of your Hawaii vacation.