Recent Sailing Charters/ Sail Blue Hawaii Sailing Stories

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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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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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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

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