Choose Hawaii’s BEST private sailing charter, Sail Blue Hawaii. Any occasion is a great one to get out sailing on the Hawaiian waters. Enjoy some relaxing and refreshing ocean time here where the air is balmy and year-round trade winds provide Honolulu with wonderful sailing conditions.
“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”
Our most popular boat tours are the private yacht charter, weddings, anniversaries and sunset sailing cruises. In addition, sailing lessons, birthdays, corporate events, life celebrations and custom adventures await.
While sailing in Honolulu we often see Hawaiian green sea turtles ( honu) lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset.
another amazing Hawaii sunset; it can take your breath away
Call Sail Blue Hawaii today for your Hawaii private sailing charter. It could well be the highlight of your Hawaii vacation.
Sail Blue Hawaii offers private sailing charters in Honolulu aboard the 42-foot Beneteau yacht named Kaikiwi. These custom tours are tailored to your preferences, allowing you to choose the time of day and duration that suits you best. Whether you’re interested in a sunrise sail, a romantic sunset cruise, or a leisurely/ robust day sail, the consistent trade winds in Hawaii ensure a pleasant sailing experience at any time. Custom sailing includes proposals, weddings, life celebrations and ash scatterings; any occasion is a good one to sail with Sail Blue Hawaii.
Highlights of Sail Blue Hawaii’s Private Tours:
Customizable Itineraries: You can select from sunrise, morning, afternoon, or sunset sails, depending on your schedule and preferences.
Comfortable Yacht: The Kaikiwi features both covered (lots of shade) and open-air seating, along with an onboard restroom, ensuring comfort.
Variety of Experiences: Popular options include coastline sightseeing, Friday night fireworks viewing, and special events like birthday celebrations and anniversaries.
Experienced Captain: Captain Gaelyn brings extensive knowledge and a passion for sailing, ensuring a safe and enjoyable experience. (https://www.sailbluehawaii.com/about-us/)
Affordable Pricing: Private charters are competitively priced, often comparable to shared tours, offering a more personalized and intimate experience.
Location: Kewalo Basin Harbor, 1025 Ala Moana Blvd, Honolulu, HI 96814
If you need assistance with booking or have specific questions about the tours, feel free to ask!. If captain’s hands are on the wheel, a call to personal line (808) 347-0235 will have a slower response time than a text.
As captain of your private sail boat, I am honoured to help facilitate your Hawaii ash scattering/ life celebration at sea.
Your ash scattering includes a private sailing charter
A reflective sail to Diamond Head establishes the mood for your ash scattering/ life celebration. How often are we surrounded by rainbows during this boat tour? Almost always. Talk about setting the mood!
Take as long as you need to talk about your loved one as you scatter their ashes and celebrate their life. Bring as many un-strung flowers/petals as you want. When all is done, an easy down-wind sail brings you back to the harbour.
When is the best time to sail?
Anytime is good…sunrise, sunset, morning, afternoon..you choose.
I hope your days here in Hawaii have lots of sunshine and brightness to them. Hawaii is such a healing place…immerse yourself in that richness while here, and take it with you when you leave.
Choose Sail Blue Hawaii for your Hawaii ash scattering/ life celebration.
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.
An unusual Hawaii sunset cruise turns into an evening at sea under windy LUMPY ocean conditions.
a sunset cruise for one..me
29 July 2025
From an unusual (solitary) sunset cruise to an unplanned evening at sea. I haven’t seen so many boats out EVER! An 8.8 earthquake off Russia’s SE peninsula caused tsunami warnings all around the Pacific Rim and the Hawaiian islands.
Let me say, there is nothing more chilling than hearing wailing WW11-type sirens ringing out. The first of those sirens happened as my afternoon charter and I were motoring down the channel on our way back to the slip. I could tell it un-nerved my charterers too.
So, I dropped them off at the dock, called my sunset cruisers to cancel their charter, took my car to higher ground (a multi-level parking structure close to the harbour) and left again; this time alone…hence “a very unusual sunset cruise”
At 3 miles out, ocean conditions were cold, windy, LUMPY, BUMPY, GRUMPY. I popped a little headsail and sailed slowly back and forth, eagle-eyed to keep an eye on others doing the same, with one ear on my handheld VHF radio monitoring updates, the other on my cell phone for incoming useful texts. Officially, we were under a tsunami warning, waiting to hear it be dropped to an advisory so we could all safely head back in to the harbour. It took what seemed like forever, but it could have been so much worse. Hawaii had very little damage and I was safely tied back up at the dock by 12:45 am. I thought I’d be sleeping on Kaikiwi for the night but, believe it or not, despite being bone-tired, I was kinda wired… not to mention there is no coffee on board! That I could not tolerate. I must take care of that immediately.
I drove home with the top down, the crescent moon setting behind me, more but a pleasant wind keeping me awake. There was hardly a car on the road. Such a contrast from the stuck traffic, moving an inch a minute, when I moved my car to higher ground.
Mahalo to all who reached out to me last night to let me know the news and details that were so sorely missed on channel 16, monitored by the US Coast Guard. At midnight USCG were still saying ” a tsunami warning has been issued for the Hawaiian Islands. The first wave is expected at 7:17pm….” thats enough to drive a girl crazy. I learnt more from the guys who were using channel 16 (illegally) to chat with each other, despite the reprimands from the coasties. LOL.
All is well in paradise. We dodged a bullet this time but it reminds us how vulnerable we are. We may not be so lucky next time. Oahu needs to have a better plan to get people to higher ground faster and with less chaos. They must handle this. And I must handle all I am capable of at my end. AND that includes getting some fresh ground coffee on board.!
I don’t need another unusual sunset sail any time soon. The next sunset cruise, or any of the wide range of private sailing charters offered, I hope to do with you! Call Sail BLUE Hawaii to book yours today. (808) 347-0235 capt.gaelyn@sailbluehawaii.com
