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.

“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

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

February 3, 2025

Let’s go Sailing in Hawaii

Sail Blue Hawaii on Oahu provides an unparalleled sailing experience, offering guests the chance to explore the island’s breathtaking coastlines and clear azure blue waters. Whether it’s a romantic sunset cruise, a private sunrise cruise, a tradewind sailing adventure, or a relaxing day-sail, Sail Blue Hawaii’s knowledgeable captain ensures a personalized and memorable journey across Oahu’s stunning seascape. Let’s go sailing in Hawaii !

What kind of vessel will we be sailing?

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

Kaikiwi is a 42-foot Beneteau 411 and 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.

Kaikiwi is offered for day-sailing only (up to 6 passengers). Inter-island/ overnight charters are NOT currently offered. Larger vessels, for 7 + passengers, are also available for all DAY-sailing occasions and custom cruising.

Kaikiwi has lots of shade so time of day does not affect heat/ sun exposure. Sailing in summer months is very very comfortable even in the middle of the day.

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

I am surprised by the number of clients who come to me and say “I’ve always dreamed of sailing but never had the chance until now”. Or, “all my life I have wanted to learn how to sail. Thank you Sail Blue HI for introducing me to sailing by offering me a top-notch CUSTOMIZED sailing lesson. Wow. I want more”. A sailing lesson is a beautiful gift to give at birthdays or Christmas. It will be remembered for a life-time as a highlight. Gift certificates are available for any kind of sailing.

Let’s go sailing in Hawaii with Sail Blue Hawaii.

capt.gaelyn@sailbluehawaii.com; text: (808) 347-0235

December 30, 2024December 30, 2024

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

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.