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.

October 17, 2024

Hawaii Private Sailing Yacht Rental

You are in paradise and what could be better than to experience your very own Hawaii Private Sailing Yacht Rental ! Because this is custom sailing, we can sail any time of day 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 stunning SUNRISE over Diamond Head, tradewind DAY-SAILING, a romantic SUNSET cruise✨. It is all good.

What are people saying about Sail Blue Hawaii?

After you have read this blog, you can check out Sail Blue Hawaii’s Rave Reviews page: https://www.sailbluehawaii.com/testimonials/. More timely posts are celebrated on popular social media platforms where people who have sailed with Sail Blue HI have left their thoughts, reviews and photos (finish reading this blog first):

Trip Advisor,Yelp ,Google, and Facebook;

Instagram: https://www.instagram.com/sail_blue_hawaii/
X: @SailHawaii

Don’t Dream your Life, Live your Dream

So, again, when is the best time to sail your very own Hawaii Private Sailboat charter? EVERY TIME of day, all day long; LOL. I obviously am biased. After your time of day has been chosen, some people prefer the beginning of their vacation to relax into it by hanging back and just listening to the wind and enjoying their on-board company; others choose a day-sail according to what they feel might be the biggest wind day because they want adrenaline; others sail their last evening to relax into their final sunset. There are a myriad of choices for a myriad of personalities. It truly is all good and can be customised. So, here is what else I have heard from clients:

This group sailed the first or second day of their vacation; after the sail it was stated: “anything after this is going to be boring!” (oh no! They did of course find plenty to excite them through their week. HOWEVER, we do all know hot exclamation in the moment !)
This group sailed the first day of their vacation: “What a terrific way to begin our vacation! We cannot wait for tomorrow”!
“Sailing with you has been the highlight of our vacation”. From groups who have been on island a few days through to their very last day. Extremely sad to be leaving they ask: “Can we come back tomorrow PLEASE”. Cute. Do come back, yes, or next year!! (I have had a group who had so much fun they did come back “tomorrow”; another “next week”.)
“What an incredible way to finish our vacation ..the best activity, the best day of them all. THE HIGHLIGHT. ” Final-day vacationers.

Dreams do come true in BLUE Hawaii

Whether you want to see sunrise over Oahu, go for a “real” full-sail tradewind sail way south on the cobalt blue blue of our beautiful pacific, or slow down for a romantic cruise at sunset, Sail Blue Hawaii can give you your very own Hawaii private sailing yacht charter. All levels of adrenaline (or none) catered to 🙂 YOU WILL NOT BE DISAPPOINTED.

For SAIL BLUE HAWAII, THE HORIZON IS NO LIMIT!

September 28, 2024September 29, 2024

Waikiki Sailing at its BEST!

Private boat tours in Waikiki are available with Sail Blue Hawaii. Weekends and holidays fill quickly so plan ahead and book today. Your experienced captain will ensure your safety and enjoyment. The cost of a private boat tour in Waikiki is affordable and highly desired. Your private yacht is spacious, featuring covered and open air seating as well as an onboard restroom.

Dreams come true in BLUE 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 cruise, tradewind day-sail, SUNSET cruise✨. It is all good. A client this week was concerned if we left at 0800 for a 3-hour sail we wouldn’t have enough wind. So much sailing, anywhere in the world, relies on an afternoon sea breeze. The fact is, we rely on tradewinds and not sea/land breezes. This makes Hawaii sailing unique and desirable, ANY TIME OF DAY. His concern was also the mid-day heat. “Kaikiwi” has lots of shade, so, time of day does not affect heat/ sun exposure.

Don’t dream your life, live your dream

Private Waikiki boat tours with Sail Blue Hawaii are for both tourists and locals looking to rent a private boat. Tradewind sailing, sunset cruising, coastline sightseeing and Friday night fireworks are among the most popular tours in Waikiki. Birthday and life memorials are also very popular. We accommodate a wide range of special events aboard. The Horizon is no limit.

So, give Sail Blue Hawaii a call for your own private boat tour in Waikiki.