Private Charter Oahu

Vacationing in Hawaii MUST include a private charter while on Oahu. “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.

Should we book at the beginning or end of our vacation?

Of course, this is a personal preference. Some choose day-one to get over their jet lag and, before they left home, already booked a private sailing charter with Sail Blue Hawaii for day-two. This is perfect. You can sit back and relax, taking in the stunning sights of ocean and land. Having this “do-nothing” second day of vacation will pump you with the excitement and wonder that is Hawaii, while adjusting to Hawaiian time.

Others choose the last day for their private Oahu charter. Before they leave home they book, most commonly, a beautiful and unforgettable sunset cruise. This highlight is keeping them warm and happy as they pack their bags for the cold flight home. An adventurous day-sail is also a common option. Photos and videos of this last day on Kaikiwi, their private Oahu sailboat, keep their memories flowing, certainly taking much HI home with them.

Better, yet. Sail both :-):

“Our first sail was so exceptional that I texted her just a few days later to see if we could go out again before returning home. Our second sail was even more spectacular than the first. The trade winds were perfect, the scenery was breathtaking, and once again, Captain Gaelyn made the entire experience educational, comfortable, and memorable, including seeing sea turtles and dolphins in the distance. Starting and ending our vacation on the water with her was truly special, and it’s an experience I will carry with me forever. I cannot recommend Sail Blue Hawaii enough, especially for anyone who wants to experience the beauty and thrill of true ocean sailing. I will absolutely be referring all of my sailing friends to Captain Gaelyn and Kaikiwi Sail Blue Hawaii. Captain Gaelyn, thank you for sharing KaiKiwi with us!” you are so welcome!!!

So there you have it ! Book your private charter Oahu today with Sail Blue Hawaii. Pre-booking before you leave home, ensures the charter day and time of your choice…beginning, ending, middling…or all THREE! LOL The season ahead is busy..time slots fill fast so do pre-book a week or two out.*** Local or tourist…set your holiday season with the gift of Sail Blue Hawaii’s private charter Oahu … pleasure guaranteed!

(***last-minute bookings are of course also accommodated, room permitting)

November 8, 2025November 21, 2025

Hawaii Tradewind Sailing at its Best

Welcome aboard Sail Blue Hawaii to experience Hawaii tradewind sailing at its best. Leave the tour bus behind and experience something different and unique…it may well be the highlight of your Hawaii vacation.

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. This is not “destination” sailing. “Destination” is sailing.

What if I have never been on a sail boat before?

The beauty of a private sailing charter is that the experience your little group has is customised (Kaikiwi is USCG certified for 1-6 passengers). You don’t need to have ever sailed before: I can tone it down or ramp it up to meet your group’s needs and expectations. Sailing outside Diamond Head is not for everyone. So, if your group decides so, we don’t go. It’s easy enough; just tell me who you all are… newby or a seasoned sailor, or part and part.

Email capt.gaelyn@sailbluehawaii.com today to book your Hawaii tradewind sail. The beauty and quiet of your private sailing charter may well amaze you.

View other movies on Sail Blue Hawaii’s YouTube channel !

August 12, 2025September 18, 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 too! The range is limitless. Just voice your pick.

DON’T DREAM YOUR LIFE: LIVE YOUR DREAM

June 30, 2025July 13, 2025

Hawaii’s BEST July 4th Boat Charter

Enjoy Hawaii’s BEST July 4th boat charter…whether you are local (or, ESPecially if you are local !!) or tourist, you will not regret sailing with Sail BLUE Hawaii. The experience may well be the highlight of your HI vacation or the end of your work week.

Where do we go?

“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.

Because this is custom sailing, we can sail any time of day you want and whatever length of time you wish. Our islands are almost consistently graced with trade winds so any time is a good time to go sailing…✨✨✨magical SUNRISE cruise, full-sail morning and afternoon, romantic/ peaceful SUNSET cruise.✨✨✨ It is all good.

July 4th Fireworks

The Waikiki fireworks show that were especially dynamic, are still not happening after a long break since the pandemic. If you wish to see fireworks from your private yacht, they will appear from far away; after the 8pm Hilton show. Worth staying out late for? Maybe. Either way, choose your time of day and enjoy your day off by laying back on your private sailing charter. Choose Sail BLUE Hawaii, Hawaii’s BEST custom July 4th private boat charter.

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”.