sailboat – Private Sailing Charters, Honolulu, Oahu, Hawaii

August 12, 2025

Hawaii’s BEST Tradewind Sailing

Sai! Blue Hawaii offers a full range of sailing options; from casual sightseeing boat tours to special occasions (weddings, proposals at sea) to Hawaii’s BEST tradewind sailing. Whether you have never stepped foot on a sailboat before (exciting first time !!) or you are an old salt, your private sailing charter is catered to you. (Visit the “Let’s go Sailing” page for ideas.)

Where do we sail to?

“Kaikiwi” sails from Oahu’s (protected) south shore, near 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. We do look for mermaids too. The first to see one gets a free boat ride. 🙂
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.

Whoever needs to arrive to be happy?

Where in the world are you going to get this kind of tradewind sailing? Only here in Hawaii ! Sai! Blue Hawaii offers Hawaii’s BEST tradewind sailing daily on your vey own private sailing charter. Other companies may pop a little sail out but mostly motor-sail. Sai! Blue Hawaii offers REAL sailing. Who needs a theme park when you can do this for real? Remember, gentle sailing is offered for those less adventurous! The range is limitless.

March 24, 2025March 24, 2025

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

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.

September 25, 2023September 25, 2023

A perfect Honolulu Sunset Charter

Honolulu sunset sailing… a beautiful time of day to be on the water. What can be more romantic than sunsets aboard a sailboat in the pacific ocean. This tour is definitely something you’ll want to experience on your vacation in Honolulu. Here is our recommendation on the 5 best Honolulu sunset sailing ideas.

5 Best reasons for a Hawaii sunset cruise

Friday night fireworks in Honolulu. This is the most popular and something everyone enjoys while on vacation in Honolulu. Summer only.
Birthday celebrations at sea. What better way to celebrate that special day than on board a private yacht charter in Honolulu?
Wedding and Engagement. Something truly unique, this is a way to make this day special. Several party planners in Honolulu highly recommend our services to guests visiting Hawaii.
Corporate Events. Celebrate with the team onboard a luxury sailing yacht in Honolulu. How better to raise moral and reward them for a job well done?
Hawaii Ash Scatterings and Memorial Services. Remember that special person in your life. We realize that it’s a very difficult time losing a loved one and we are here to help.

There is no better way than to wind down your day with a Honolulu Sunset cruise.

September 16, 2022September 16, 2022

The Best Private Sailing Charter 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 is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET.✨ It is all good.

Book a Waikiki private sunrise cruise

Maybe you’ve just flown in from the East Coast and Waikiki doesn’t wake up early enough for you. Let’s go sailing and catch sunrise over Diamond Head. It is possible that we’ll see dolphins in the beautiful morning light. Bring your favourite coffee and muffin. It’s so exciting to board in the pre-dawn hours and head out the channel in the dark. The anticipation of sunrise is palpable. Imagine, your own private sailboat, ON YOUR FIRST DAY OF VACATION, sailing towards one of the most famous landmarks on the planet, Diamond Head! It is exciting, thrilling, magical. AND this could be YOU!

Before you leave home, call Sail Blue Hawaii for a private sailing charter. Did you forget to do that and you are already on island? Give Sail Blue Hawaii a call and hope the sunrise cruise is still available. You will not be disappointed.