Private Hawaii Sailing Charter

While sailing off the Oahu coastline, 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 will thrill. You can choose a magical sunrise cruise, an adventurous tradewind day-sail, a romantic sunset cruise; depending on your preferences and schedules…anything is available for any occasion. 

Why a private sailing charter?

Your private sailing charter in Hawaii is perfect for intimate gatherings, family vacations, or romantic getaways. It comes with an exceptionally experienced captain and crew who are knowledgeable about the islands’ marine life, culture, and history. You will enjoy tradewind sailing as only Hawaii can offer. 

What will we see?

The stunning coastal landscapes, crystal-clear waters, and the chance to see marine wildlife up close makes your private sailing charter an unforgettable experience. However, it’s essential to book in advance, especially during peak tourist seasons, to ensure availability and secure your preferred sailing date.

Tradewind sailing at its best. Call Sail Blue Hawaii today for YOUR private Hawaii sailing charter.

Private Hawaii Sailing Charter

TODAY call Sail Blue Hawaii to book your dream private Hawaii sailing charter. Kaikiwi, a 42 ft Beneteau, is the perfect choice for any and all occasions. Whether you want an adventurous tradewind sail (we are the only ones who will sail you out past Diamond Head, and only if that’s what you want!!), a sailing lesson, a more relaxed kick-back sunset cruise..whatever it is…you dream it, we will sail it.

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.

Why choose a private sailing charter?

You’ll sail in the safety of your own private bubble. How perfect is that during this challenging time? Your private sailing charter in Hawaii offers you an incredible opportunity to explore the stunning waters of the Hawaiian Islands in a luxurious and personalized way.

Feel free to create your own custom cruise.  We will cater to your every whim.  Call Sail Blue Hawaii for your special occasion and we will design the sailing charter of your dreams.

Do you have someone special in your life and just can’t find the right way to say “thank you” or “happy birthday/anniversary”?  Stun them with a GIFT CERTIFICATE.  It could well be the best gift they have ever received. 

The horizon is no limit.

Kaikiwi is a beautiful 42ft Beneteau. The best-kept yacht in the islands!

Email, text or call TODAY for your private Hawaii sailing charter.

Sailing Yacht Rental Hawaii

Our current tradewind flow made for a beyond awesome day-sail yesterday for a couple’s sailing yacht rental while in Hawaii. Typically, for a private day-sail charter, clients choose 2-, 3- or 5- hour sails. Because yesterdays’ tradewinds were in the range of 15 knots we were able to sail way beyond the Diamond Head wind line. Fabulous. We found a false orca whale swimming around..that is a seldom sight.

What time of day is best for a private sail 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.  You can email Sail Blue Hawaii NOW to sign up for a sunrise cruise, a day-sail, or a magical sunset cruise.

Where are we sailing to?

While on your private sailing yacht rental, we sail 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.

any time is a good time for a private sailing charter but a sunset cruise is for romantics

Email Sail Blue Hawaii today to get your custom quote for your private sailing yacht rental. It’s the best money can buy.

Let’s Go Sailing Oahu

Kaikiwi sails from Oahu’s south shore. You will embark at Kewalo Basin boat harbor, not far from Waikiki beach hotels. We sail past beautiful coastline in the cobalt blue blue waters of our Pacific. The south shore is the protected side of Oahu: calm and crystal clear, making it the perfect sailing destination.

Why go sailing Oahu

Common marine wildlife sightings on Oahu are for example, Hawaiian green sea turtles, honu, dolphins, nai’a, and humpback whales, kohola (in winter season only). In addition, flying fish, malolo are some of the critters we may see as we sail about the island. Sunrise cruise, day-sail, sunset cruise, private sailing lessons, ash scattering..are all available. This is custom cruising at it’s best.

Incredible sights while sailing

Beautiful breathtaking views of Diamond Head are just one of the highlights while sailing in Oahu. On clear days, although far in the distance, Molokai and Lanai can sometimes be seen from the island of Oahu. This is not destination sailing, destination is sailing!

While Kaikiwi is a US documented vessel she does like to fly the kiwi flag. All nationalities invited to sail!:

Email Sail Blue Hawaii today for your custom cruise. Let’s go sailing Oahu!

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: