Hawaii’s 5 Best Private Sailing Charter Ideas

Oh the luxury and awe of sailing your own private yacht in Hawaii. “Kaikiwi” is 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, a sailing afternoon with family and friends, whale watching, entertaining business colleagues, saying “I do”, or an overnight/inter island adventure; (but that makes 6 best ideas…and I could keep going:-); 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.

The best first mate ever!

Hawaii private sailing charter

Your Hawaii private sailing charter 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. 

A private sunrise sail to remember

It was a beautiful chilly morning when we left the dock before sunrise. The sky colours changed every minute, it seemed, as we sailed towards Diamond Head. The sunrise clouds coloured every point on the compass.

Along the way, in the precious still of the morning, we dropped sail to scatter ashes of their loved one, flowers following. It was magical, peaceful and a tender way to start the day.

Get in touch with Sail Blue Hawaii for your private sailing charter. Your private boat tour will include magic that you couldn’t even anticipate.

Hawaii ash scattering/ life celebration

As captain of your private sail boat, it is an honour to help facilitate your Hawaii ash scattering/ life celebration at sea.

Your ash scattering includes a private sailing charter 

A reflective sail to Diamond Head establishes the mood for your ash scattering/ life celebration. How often are we surrounded by rainbows during this boat tour? Almost always. Talk about setting the mood!

Take as long as you need to talk about your loved one as you scatter their ashes and celebrate their life. When all is done, an easy down-wind sail brings your back to the harbour.

When is the best time to sail? Anytime is good…sunrise, sunset, morning, afternoon..you choose.


I hope your days here in Hawaii have lots of sunshine and brightness to them.
Hawaii is such a healing place…immerse yourself in that richness while here, and take it with you when you leave.

Choose Sail Blue Hawaii for your Hawaii ash scattering/ life celebration.

Private Boat Tour in Waikiki

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

Waikiki Sailing Charters Private Boat Tour

Kaikiwi is a 42 ft Beneteau

Private Waikiki boat tours with Sail Blue Hawaii are for both tourists and locals looking to rent a private boat. Sunset cruises, tradewind sailing, 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.

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

A Honolulu Private Sunset Cruise

It’s July and Hawaii’s tourism is back and everyone (almost) is signing up for and loving a private sunset cruise.

Last night’s sunset cruise was a celebration of a young man’s graduation and birthday. What a great way to celebrate and in your own safe bubble! Whether its a day-sail or a sunset cruise, there is nothing better than being out on the water. The peace and tranquility will treat you.

A private sailing charter to remember

Sailing on Kaikiwi last night, what we didn’t expect to see were rainbows. That’s a winter thing…this is July! The rainbows followed us most of our sunset cruise. They were powerful and beautiful and most of them were double.

Give Sail Blue Hawaii a call and sign up for your own private sunset cruise, whether to celebrate something special or to just BE…out on the water where everything is magical.

This brilliant photo, framing Diamond Head in a full rainbow, was taken by Wendi Aengus, the young man’s mum