A private day-sail in Hawaii.

From sun-up to sun-down, Sail Blue Hawaii offers you the best private day-sail in Hawaii that money can buy. Feel the tradewinds blow and delight in dolphins playing in the bow wake as you set sail. Private sailing charter options are limitless: kick-back sailing, full-sail adrenaline-rushing heeling, sailing lessons, relaxing sunset cruise, a boat tour, ash scattering, life celebrations, saying “I do”, saying “I will”, multi-day charters, corporate fun(ctions), custom cruises…For Sail Blue Hawaii, the horizon is no limit.

We are the Rainbow State

and it is thrilling to sail with the awesome beauty of rainbows all around us. But, you say, where there are rainbows, there is rain. Not over Sail Blue Hawaii.

How can that be? The mountains catch the clouds, giving us blue skies while we are sailing the azure blue Pacific. It is thrilling and never tiresome.

In the case of inclement weather (Captain’s call; day of…please put the weather app/ forecast away while you are on vacation. They are very general and very misleading and don’t consider our microclimates. It’s always raining somewhere in Hawaii but seldom on Sail Blue Hawaii. I have you covered..I don’t want to be out in nasty weather either!.) every attempt will be made to re-schedule your charter. If this is not possible, there is no booking or cancellation fee.

Give Sail Blue Hawaii a call TODAY to book your private day-sail in Hawaii.

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 sailing lesson

Help set the sails, and take the helm if you like, as you learn the “ropes” of sailing. In your Hawaii sailing lesson, the first thing you learn: they are not ropes.  They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. Your Hawaii sailing lesson is for all levels of sailing experience.

“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”

Sailing is clouded in romance. Many people dream of a life of sailing and the adventure of perhaps one day sailing to distant shores. The reality is often different than the dream and this is important to understand.

So, before you go buy that boat, come sailing with me and begin or continue learning the skills that will gain you confidence and give you a whole bunch of joy as you succeed. Your time “out there” will also give you a taste of what true blue-water sailing is all about.

You don’t have to have the dream of distant shores to sign up for a lesson…you can begin by taking up sailing as a day-hobby.

Do you have someone in your life who has always had an itch to try sailing but has never had the opportunity? Buy him/her a gift certificate for a private sailing lesson. It will be the best present they have ever had! It is a WOW!!

Whatever your goal is, the lesson will fit.

Even if you are the only one who wants to learn and you don’t wish to come alone, your friends/ family are welcome on board and can enjoy the sail while you learn.

So, whether your dream is to sail the Waikiki coast or beyond that horizon (a multi-day charter is perfect for introducing you to all aspects of sailing and living aboard), your personalized Hawaii sailing lesson is waiting for you!

Having fun!! Perhaps it doesn’t look like 25 knots but those on board know very well that it is.