Category: Sunset Sail

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Hawaii Private Sailing “off the beaten track”

Set the tone (adventure, romance, fast sailing, slow easy sailing…) for your New Year and book a Hawaii private sailing charter A client this week (I am always interested, of course, how customers navigate to my site) said he had searched ” ‘un-touristy’ sailing charter”. ha ha. I love that Sail Blue Hawaii is thought of as different, AND un-touristy! Indeed, Sail Blue Hawaii does offer a different ocean experience than the many many catamaran tours (you’ll find online) where you “sail” with 59 of your closest friends. A novel approach another customer took to find exactly what she wanted was by the use of A.I “CoPilot”. Her request was immediately answered with the details sought and the suggestion of: “email capt.gaelyn@sailbluehawaii.com”. Do just that and you’ll find that we are priced right to get you out there.

5 best ideas that makes Sail Blue Hawaii unique and different

  1. We raise sails at the beginning of your charter and sail the entire time. For Hawaii, where many others motor or motor-sail, this is a unique treat. Sailors love this, as does everyone else…newbies too. Welcome aboard a true sailing charter.
  2. You have a uniquely private sailing charter. This means it’s only you and your family group. Perfect for romantic couples and celebrations too. No flu-bugs here.
  3. This is custom sailing. Unlike other companies who have a strict timetable, you can sail any time of day you want and whatever length of time you wish. No one else on island offers this: you are limited to their schedule. Our islands are mostly graced with consistent trade winds so any time is a good time to go sailing.
  4. Sailing lessons are offered for those wanting the taste. When else could one have the opportunity to put their hands on the wheel of a beautiful pricey yacht? Certainly no one else in Hawaii offers sailing lessons without you first signing up for the rigid ASA program on sub-par sailboats.
  5. You get to bring your own food and beverage. With today’s dietary needs, nothing is worse than having a pre-catered expensive menu, with foods you cannot eat, and having that cost hidden in your charter fee. You will appreciate this too if you have keiki.

HAVE A HAPPY NEW YEAR

by setting sail with Sail Blue Hawaii. You can navigate to the website with tag “un-touristy” sailing and/or using A.I. with your unique request. You’ll leave the chaos of snorkeling with a hundred others to others and appreciate the QUIET and PEACE of true sailing. There is no crowd as you leave the tour bus and the overloaded tour catamaran behind. The wind is our engine and the ocean is our song. You will not be disappointed with your choice of Hawaii’s best private sailing “off the beaten track”.

NO RULES! Bananas on board is OK with me 🙂

DON’T DREAM YOUR LIFE, LIVE YOUR DREAM

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5 BEST reasons to choose a Private Hawaii Sunset Cruise

Honolulu sunset sailing: a beautiful time of day to be on the water. What can be more romantic than sunset aboard a sailboat on the Pacific Ocean. You will want to experience a sunset cruise during your vacation in Waikiki. Here are the 5 best Hawaii sunset cruise ideas:

Honolulu’s Best Sunset Cruise

  1. Have you ever seen the green flash? On your private sunset sail, this may well be what captures your joy the most. There are theories about what makes the green flash. Check them out online. I have seen more than my share of this delicious phenomenon on numerous sunset sails.
  2. The other evening, my charterer pulled off an especially perfect surprise sunset cruise for his girlfriend. She had no idea she was about to go sailing until she got to the dock. She had always expressed a desire to be on a private sail boat/ a private boat tour. It was with teary eyes she climbed on board.
  3. Of course, saying “I do” is particularly romantic at sunset: a private yacht, just the two of you and the captain. YES, this is the perfect reason to choose a sunset cruise. Sail on a Friday evening and enjoy a fireworks display just for you! A combined sunset and fireworks cruise is a highlight…how can she say anything but “yes”in this most romantic ambiance.
  4. A life celebration/ ash scattering is particularly special in the easy sunset hours. Your sunset sail with family and friends will stay in your mind forever as you remember and celebrate your loved one.
  5. Of course, you need no reason at all to choose a Hawaii sunset cruise. It is the best time of a day. Sail out there and enjoy all that Hawaii’s beauty has to offer.

Call Sail Blue Hawaii today and sign up for your own private sunset cruise. If you are especially lucky, in the winter months, your private sunset cruise may well turn into whale watching! This Hawaii Sunset Cruise could well be the highlight of ANY vacation.

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Private Hawaii Boat Tour

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.

Booking Information:

  • Contact: Email: capt.gaelyn@sailbluehawaii.com​ is the best way to connect.
  • Phone: (808) 347-0235​….but TEXT is BEST
  • 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.

DON’T DREAM YOUR LIFE: LIVE YOUR DREAM

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Hawaii Ash Scattering

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.

(turn on your sound)

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An Unusual Hawaii Sunset Cruise

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

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