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 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.

Hawaii Marriage Proposal

The Hawaiian islands are known for their romance. So, what could be more perfect than saying “I will” aboard your own private yacht at sunset. Yes, your 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 the years to come. You will look back on this evening as not just the highlight of your Hawaii vacation, but the highlight of your lives. Your private Hawaii marriage proposal will set the tone of your lives together as you sail off into the sunset.

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.

5 top sunset/full moon 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 sunset/ full moon 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 sunset/ full moon cruise will be the highlight of your Hawaii vacation.

WOW!