Tag: honolulu

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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)

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Hawaii’s BEST Private Sailing Charter

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.

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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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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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Hawaii Ash Scattering turns to Whale Watching

May 21, 2025 was a beautiful day on the water to celebrate a life and scatter the ashes. It’s never easy, but when ocean conditions lie down flat or the wind ramps up , it is often a reflection of the character of the soul we are scattering. No kidding, this happens often.

May 21, 2025. I mention the date again because Hawaii whale season ends late March /early April. Sailing slowly back to the harbour in a reflective mood we were suddenly stirred by the sight of a mum and calf surfacing as they swam west. WOW!

You never know what your Private Sailing Charter will capture

Every day is different. In my many, many sea hours I am still captured and delighted by the many unusual happenings as I sail each Hawaii private charter. I had someone ask me the other day, “don’t you get bored doing the same thing every day”? I was speechless. Never, ever, NO. Every day is different and you really can’t beat sailing out to scatter ashes and meeting a mum and calf on the way home, in MAY. That is a first for me. Just exactly who was this person we had just said “aloha” to anyway ?

For Sail Blue Hawaii, the horizon is no limit. Choose your own particular type of Hawaii private sailing charter. The choices are endless. (Use the link below to peruse). Your custom adventure on our beautiful Pacific may well be the highlight of your Honolulu, Oahu, Hawaii vacation.

Let’s Go Sailing
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