Private Sailing on Oahu

A perfect end to 2022 would be a private sailing charter while in Hawaii. What better way to kiss the year goodbye than to treat you and yours to a sunrise cruise; a sunset cruise; a fireworks cruise; or a day-sail. 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 is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET.✨  It is all good. 

What time of day can we see marine life?

Any time is good. Our marine life don’t have a schedule. They are either close by or not. “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.

A fireworks cruise is a romantic way to bring in the New Year.

Book now for your private sailing charter on Oahu.

Whale Watching in Hawaii

Call Sail Blue Hawaii for your private whale watching cruise. While whales are not guaranteed, this is the season for a whale sail. “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 type of whales do we see?

In winter, humpbacks are Hawaii’s most famous tourists, making their annual 3,500 mile trip from Alaska to the islands each December through April.  We’ll set sail and hope to find these gentle leviathans. They swim all the way to Hawaii to have their babies in the gentle warm waters. Can you imagine?

sign up today for your private Hawaii whale watching cruise

Private Sailing Charter in Hawaii.

When you book your private sailing charter while vacationing in Hawaii it may well be the highlight of your vacation. It is astonishing how many times my clients have said that to me. That is thrilling. It is exactly why I have worked so hard to give people the best-kept charter vessel in the islands, AND the best private sailing charter experience. That was my goal when I set up up Sail Blue Hawaii LLC.

“This is the best time I have had in my entire life.”
-Kaelyn, age 7, CA

Why choose a private sailing charter?

There are so many reasons, but let me name a few:

  • CoVid is still around. Your captain is vaccinated and boosted. How better to keep you and your loved ones safe. When you sail on “Kaikiwi”, a 42-ft Beneteau, you will feel so safe especially when you see the over-crowded catamarans.
  • delight in pure trade wind sailing any time of day for as many hours as you want.
  • whale sail. In winter, humpbacks are Hawaii’s most famous tourists, making their annual 3,500 mile trip from Alaska to the islands each December through April.  We’ll set sail and hope to find these gentle leviathans.
  • birthday parties
  • corporate fun(ctions)
  • very popular: summer only; Friday night pau hana fireworks cruise. Combine this with sunset and you have the perfect cruise.
  • for romantics: sunset cruise: a beautiful time of day to be on the water.
  • maybe you’ve just flown in from the East Coast and Waikiki doesn’t wake up early enough for you. Let’s catch sunrise over Diamond Head. Maybe we’ll see dolphins in the beautiful morning light.
  • choose the one night of the month (or, the “blue moon” second night of the month) to sail from sunset to full moon. It is truly magical to see the full moon rise over Diamond Head after sailing into the sunset. Click moon phases to see full moon calendar.
  • when the moon is close to its new phase, we have fabulous star-gazing.  Set sail for sunset and a night sail. In winter months, the iconic Southern Cross can be seen.
  • proposal:  how more romantic can you get when you propose to your loved one while sailing into the sunset?
  • weddings for romantics:  there’s nothing more special than saying “I do” under a tropical sky  while sailing into the sunset.  Your captain will marry you with a personalized  service on your own private yacht.
  • renewal of vows:  what a “wow” it is to  say those vows again, to remember and  re-ignite!
  • sailing lessonsHelp set the sails and take the helm if you like as you learn the “ropes” of sailing.  The first thing you learn: they are not ropes.  They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. For all levels of sailing experience.
  • memorials, ash scatterings and life celebrations
perfect tradewind sailing

Hawaii’s BEST Private Sailing Charter

Any occasion is a great one to get out sailing on the Hawaiian waters to enjoy some relaxing and refreshing ocean time. Especially true here in Hawaii 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, custom adventures await.

While sailing in Honolulu we often see Hawaiian green sea turtles lazing in the sun, dolphins jumping the bow, whales (winter only) spouting off to starboard, and the stunning shine of Venus at sunset.

Call Sail Blue Hawaii to day for your Hawaii private sailing charter. It could well be the highlight of your Hawaii vacation.

Hawaii whale watch

It was a fabulous afternoon with tradewind sailing at its best while enjoying our Hawaii whale watch. Captain Gaelyn managed to find two sets of mom and calf humpbacks in the bay. Our private sailing charter was also blessed with dolphins swimming in Kaikiwi’s bow wake. I had read on her website: “watch spinner dolphins surfing the bow wake” but thought that an exaggeration. Nope! much to our delight.

Honolulu’s best private sailing charter

It is perfect in today’s world to sail with Sail Blue Hawaii. We choose Captain Gaelyn and her “Kaikiwi” because of her beautifully maintained sailboat and the “private” sailing charter. Keeping family safe while having fun on the ocean was our priority. Humpbacks, dolphins, turtles, flying fish… all in one fabulous balmy afternoon. When we wrote for information on her private sailing charter, she wrote back:

“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.

We didn’t miss out on one single thing in that very wordy paragraph. Cobalt blue blue? Understated! Wildlife? They were all out to play. Molokai and Lanai were both there, yes, in the distance. Destination? Sailing!

Whether you are signing up for a Hawaii whale watch, a sunset cruise, a sunrise cruise, or just an afternoon of private sailing, write for your custom quote today. Sailing with Sail Blue Hawaii could well be the highlight of your Hawaii vacation. Locals welcome too 🙂

“It appears he is adapting to this social distancing thing pretty well.” -/ courtesy of Boat US magazine.