Hawaii Private Sailing Charter

When you sign up for your Hawaii private sailing charter, you might see the first humpbacks of the season. In winter, humpbacks are Hawaii’s most famous tourists, making their annual 3,500 mile trip from Alaska to the islands each December through April.  We’ll set sail and hope to find these gentle leviathans.

Where do we sail to?

“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.

bigger than it looks

Call Sail Blue Hawaii and sign up today for your own Hawaii private sailing charter

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.

Oahu’s Best Private Sailing Charter

When is the best time to book a private sailing charter on Oahu? 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. 

Will we see marine life on our private sailing charter?

Because Hawaii’s waters are relatively warm, this means our waters can be sparse in terms of wild life. Not to be disappointed though, on your private sailing charter, you may well encounter at least 3 types of marine life: turtles, dolphins and flying fish. “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.

Call Sail Blue Hawaii now for your private sailing charter.

A Hawaii Proposal

Hawaii is a place full of romance. You will feel it the minute you get off the plane…the balmy tradewind, the scent of plumeria in the air. So, what better place on the planet than Hawaii for your proposal of a lifetime.

Hawaii Proposal at sea

You cannot get any more romantic when you propose to your loved one while sailing into the sunset. Saying “YES” under a tropical sky, on your own private yacht, will be a memory of a lifetime. Of course, you don’t need the sunset to complete your proposal: 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.

I have sailed many a couple to witness their Hawaii proposal and every single one gives me chicken skin. It is an honour. Call Sail Blue Hawaii to book your Hawaii proposal at sea.

A Hawaii Sailing Vacation

Any occasion is a great one to get out sailing on Hawaiian waters to enjoy some relaxing and refreshing ocean time. Especially true here in Hawaii where the air is balmy and year-round trade winds provide Honolulu with wonderful sailing conditions.

The possibilities are endless and THE HORIZON IS NO LIMIT.

While sailing in Honolulu we often see Hawaiian green sea turtles lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset. Leave Waikiki and the crowds behind. Step onto your own private yacht and enjoy the ride of your life. The wind is our engine as we sail the beautiful azure blue Pacific waters. The sound of the ocean is hard to beat.

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 good for up to 6 passengers.

Larger vessels, for 7 to 35 passengers are also available for all DAY-sailing and custom cruising.

Sign up for your private Hawaii sailing adventure today!

perfect tradewind sailing