Private Sailing Charter Hawaii

Because this is a custom PRIVATE sailing charter, 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, morning, afternoon, SUNSET✨.  It is all good. 

Dreams Come True in Blue Hawaii

Sail Blue Hawaii offers private sailing charters for all ages. There is no limit to children’s ages, nor elderly, as long as the latter is mobile and agile.

I can’t say enough good things about the people who find my website and sign up to sail with me. It’s a delight for me to spend Kaikiwi time with you. Whether you have never sailed before, or even perhaps never been on a boat, OR you are a seasoned sailor, I taper the sail to your comfort and/ or (:-)) your excitement. Because we are gifted with tradewinds, I can “wind it up” or “wind it down”, customised just for you and your expectations. For a more adventurous sail do choose a day-sail when we sail full sail. Sunset cruising is all about kicking back and relaxing, perhaps enjoying a cocktail. I sail with a lighter sail plan than during the day unless otherwise requested. Because our sunsets don’t tend to linger, we are back at the dock very soon after sunset. If you decide while we are out there that you would like extend your cruise to see city lights, by one half hour or more, can do. This is common, especially on spectacular evenings. No need to decide until then.

sunrise cruise

“Years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bow lines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”
-Mark Twain

Email with your charter request today. Any type of request is encouraged: proposal, wedding, ash scattering, life celebration, sailing lesson OR: you need no reason at all other than to enjoy ocean time with close ones, with the wind as your engine, and the sounds of sailing. It’s magic.

We are priced right to get you out there. I look forward to spending Kaikiwi time with you.

With warm aloha, Capt. Gaelyn (808) 347-0235 

Visit https://www.SailBlueHawaii.com for your HI sailing vacation

capt.gaelyn@sailbluehawaii.com

“There is nothing, absolutely nothing, half so much worth doing as simply messing around in boats”.  – –Kenneth Grahame

Private Sailing Charter Hawaii

Sail Blue Hawaii wishes you and yours a HAPPY 2025. If you vacation to Hawaii, make sure to book a private sailing charter with us. You will NOT be disappointed. It may well be the highlight of your HI vacation.

More next year!. Tune in then.

I look forward to spending Kaikiwi time with you.

With warm aloha,

Capt. Gaelyn

(808) 347-0235 

Visit https://www.SailBlueHawaii.com for your HI sailing vacation

“There is nothing, absolutely nothing, half so much worth doing as simply messing around in boats”. 

Kenneth Grahame

Hawaii Private Sailing Yacht Rental

Today is a great day to call Sail Blue Hawaii for your private sailing charter. Why choose a private sailing charter? In the words of those who have:

“It was sheer joy! Everything was perfect;  the water, the sky, the wind, the fish and the dolphins!!
What a way to end our stay in Hawaii!
Capt Gaelyn, your love of the water made it extra special.”

-Harold & Sheryl, Houston, TX

When should we sail?

Some sail at the beginning of their vacation to sail, often choosing an adventurous day-sail. Others prefer the end of their vacation. What better way to end your vacation than with a relaxing sunset sai?. Those who sail at the begining of their charter have said: “anything after this will be boring”. Those who end their vacation with a private sailing charter have said “sailing with Capt. Gaelyn has been the highlight of our Hawaii vacation.”

Reviews of Sail Blue Hawaii

You can go to my review tab, or see what Yelp and Trip Advisor have to say. Among the words carefully chosen have been:

“part of hidden Hawaii”
“off the beaten track”
“I have never felt so alive”
“memory of a lifetime”
“one of Hawaii’s secret jewels”

“Captain Gaelyn, sailing with you was the highlight of our Hawaiian vacation.”

I have been thinking about Maui so much. I’ve had the privilege to sail to and from, anchor off of, Lahaina many times. One stunning sunrise, on the hook, some years back:

Honolulu Private Yacht, Private Sailing Charter

In your google search for a private yacht or private sailing charter in Hawaii, SOOOO many listings come up. It is overwhelming. How do you choose the perfect yacht for you and your sailing needs? Who do you choose for your Hawaii private sailing charter. Can you trust the websites you find?

Don’t dream your life; LIVE your DREAM

While in Hawaii, what can be more perfect than getting out on the water to unwind. The wind in your sails gifts you an incredible ride on our beautiful Pacific waters. But who do you choose for this most special experience? Don’t be overwhelmed with the choices out there. Sail Blue Hawaii is Hawaii’s premiere charter company. There is a reason people choose Sail Blue Hawaii. This trusted company has been around for years.

Your safety and comfort are our number one concern: our vessels meet all U.S. Coast Guard inspection requirements.

Whether you are a group celebrating a special occasion, or a solo sailor, we have the perfect sailing yacht for you. Whether it’s a romantic sunset cruise for two, a sailing lesson, or a laid-back blue water sail, we have the perfect occasion for you.

Kaikiwi, a 42-foot Beneteau 411, is a wonderful sailing machine for Hawaiian waters. She is well-proven.  Capt. Gaelyn sailed her home from Mexico, with two crew, and was delighted with the way she handled in all conditions.

You can book Kaikiwi for day-sailing (up to 6 passengers). Or choose larger vessels for your party of 7 to 35. With Sail Blue Hawaii you book with confidence, knowing that you are well cared for. Get ready for the highlight of your Hawaii vacation on your private yacht, sailing a private charter.