Summer is perfect for Hawaii Monohull Sailing.

Whether you are a “newbie”, an old salt or in between, nothing will thrill you more than summer Hawaii monohull sailing! Why? A summertime monohull sail in Hawaii offers a style of sailing that’s hard to replicate anywhere else on the planet’s waters for many reasons:

1. It feels like real sailing

As Kaikiwi heels (leans), she responds directly to the waves and wind, powered only by the sails. At Sail BLUE Hawaii, we sail your entire charter so, instead of feeling like you’re riding on a floating motorised platform, you feel safely connected to wind and ocean.

2. Summer brings ideal trade winds

During Hawaii’s hot summer months, the northeast trade winds are generally more consistent and stronger, helping the seas to flatten out; seas are often calmer than in winter. This translates to:

  • Steady, enjoyable sailing conditions.
  • Comfortable temperatures with cooling ocean breezes.
  • Less chance of weather-related cancellations.
  • Longer daylight hours for afternoon and sunset sails.

3. A monohull creates a more personal experience

Kaikiwi offers PRIVATE sailing which limits your party to no more than 6-pax—just you, your family/friends, or your intimate other in a truly romantic setting. This stands in stark contrast to the local catamarans that pack on dozens of passengers. Specifically, you enjoy:

  • More interaction with Kaikiwi’s captain (no obligation; haha)
  • A quiet intimate atmosphere.
  • A more relaxing trip, with or without your favourite playlist; no loud thumping music that travels annoyingly over the water to neighbouring vessels; no party crowds.

4. A closer connection with nature

Without the engine, Kaikiwi under sail is truly quiet. You can hear the wind in the rigging and the water flowing along the hull. This quiet sanctuary lets us spot Hawaiian spinner dolphins, green sea turtles, flying fish, mermaids, and—later in the year—humpback whales with minimal disturbance to the animals.

5. Spectacular Hawaiian scenery

Summer sailing off Oahu offers excellent visibility for taking in our volcanic coastline, the lush Ko’olau mountains, and crystal-clear azure blue water. Every day my guests remark on the color of this Pacific Ocean water! On clear days, far in the distance, Molokai and Lanai can sometimes be seen. This spectacular backdrop sets the stage for memorable sunset sails, where warm evening light reflects beautifully off the open ocean.

6. A classic maritime experience

Monohulls have been the traditional sailing vessel for centuries. If you’re looking for the romance of sailing rather than simply spending time on the water, Kaikiwi provides a timeless experience.

7. Who will enjoy it most?

A summer Hawaii monohull sail is an excellent choice if you:

  • Appreciate authentic sailing and genuine cruising.
  • Prefer small-group intimacy over commercial crowds.
  • Want a peaceful, uncrowded ocean outing.
  • Enjoy feeling the wind and the easy, natural lull of the sea.

Experience Hawaii under sail

Reach out to Sail BLUE Hawaii for your summer monohull experience. We offer a uniquely immersive and memorable adventure. One that could well be the highlight of your Hawaii vacation.

For locals: it’s summertime. Bring your family for an experience they’ll remember as a summertime highlight…one the kids will talk about when they go back to school, making their classmates jealous and asking more.

If your goal is to experience Hawaii under sail as sailors do, a summer monohull sail on Kaikiwi offers a uniquely immersive and memorable adventure. Summer is perfect for Hawaii monohull sailing.

check out this delicious summer day last week…the couple absolutely loved their sail and the quality time sailing together gave them, soaking in a true Hawaiian summer day

Book your summer sail

Email Sail BLUE Hawaii today with your sailing request: capt.gaelyn@sailbluehawaii.com . To secure your spot on the water, please remember to include: your ideal departure time (daytime or sunset); your group size (up to 6 passengers); your preferred dates.

Private Boat Tour off Waikiki, Oahu

LAY BACK AND RELAX while your crew takes care of you. You do NOT have to know how  to sail to board and experience our beautiful blue Pacific. Sailing with Sail Blue HI can be a sit-back and relax sailing boat tour!, and, yes, a HIGH to boot!. OR, as an experienced sailor, sign up for your private sailing charter today. ( All sailing is private; all levels of experience are a perfect fit for Kaikiwi.)

Any time is a good time to go sailing

Want to do something you’ll remember forever? Last night’s sunset cruise could well be that for all on board…perfect sailing conditions, humpback whales, (call it a whale sail; a whale watch), great company and conversation, AND THE MYSTERIOUS GREEN FLASH! Want to know more about the green flash? Come sail with me at sunset.

DON’T DREAM YOUR LIFE, LIVE YOUR DREAM

SailBlueHawaii.com

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.

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.

Sail Hawaii’s Best Charter Boat, “Kaikiwi”.

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Private Sailing Charters

Oh !! the luxury and awe of sailing your own private yacht in Hawaii. Sail Hawaii’s best charter boat,”Kaikiwi”, the best-kept charter boat in the islands. She is a US Coast Guard approved vessel, perfect for any kind of Hawaii sailing. Whether it’s an intimate sunset sail for two, an adventurous day-sail with family and friends, whale watching, entertaining business colleagues, watching sunrise over Diamond Head, saying “I do” under a full moon…the reasons to go sailing on “Kaikiwi” are endless and the experience will most probably be the highlight of your Hawaii vacation.

When is the best time to go sailing in Hawaii?

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 of day is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET.✨  It is all good. 

“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 does “Kaikiwi” mean?

“Kai” in Hawaiian means “salt water”; “kiwi”… enough said (unless you are unfamiliar with the global nickname for a New Zealander). “Salt water kiwi” perfectly sums up the captain and her beloved 42-ft Beneteau :-).

Don’t Dream your Life, Live your Dream

Sail Blue Hawaii on Oahu provides an unparalleled sailing experience, offering guests the chance to explore the island’s breathtaking coastlines and clear blue waters. Captain Gaelyn, their knowledgeable captain, ensures a personalized and memorable sail across Oahu’s stunning seascape. Email Sail Blue Hawaii to sail on Hawaii’s best charter boat, “Kaikiwi”.

The best first mate ever 🙂