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.

Let’s go sailing in Hawaii and I’ll share some Boating Superstitions.

Whether you are a local or a visitor, you will well remember the summer you said ” let’s go sailing”. It’s a fabulous way to let loose, enjoy quiet and healing ocean time, spend intimate time with friends and/ or family. Whether it is a sunrise sail, a day sail, or an easy sunset cruise, send Sail BLUE Hawaii your request and treat yourself and your’s to something so delicious as a private 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…..✨✨magical SUNRISE, full sail morning and afternoon, romantic/ peaceful SUNSET.✨✨.  It is all good.  Let’s go sailing in Hawaii!

Why does Boating have Superstitions?

Sailing has centuries of tradition, and with that comes a surprising number of superstitions. Many began as practical lessons that became folklore over time. Here are some of the best-known ones—and the stories behind them.

🍌 No bananas on boats

We went diving the other day and were reminded of this; it is one that my guests most often ask me about while sailing. The background to this is the fact that bananas ripen very fast and were often hung in a hammock alongside other fruit. Whichever fruit was touching the banana skin was the one that went bad first and fast. Inedible overnight. Of course, as sailors, we like to exaggerate and embellish. Therefore,

The legend: Bananas bring bad luck, causing lost fish catches, equipment failures, storms, or even shipwrecks.

Other possible origins:

  • In the age of wooden sailing ships, banana cargo spoiled quickly, so captains rushed their voyages. Fishermen traveling on banana ships had little time to stop and fish, leading to the belief that bananas scared fish away.
  • Banana shipments often harboured venomous spiders and snakes hidden in the bunches, creating dangerous surprises for crews.
  • Methane gas and heat from ripening bananas could speed the spoilage of other cargo.

Today, many fishing captains still jokingly, or very seriously, refuse to let bananas onboard. Many boats harboured in Honolulu take this more seriously than most. Why? You’ll have to ask them. Me?*****

🍾 Never rename a boat

Sailors traditionally believe every boat’s name is recorded by the sea god Neptune. Changing the name without first “removing” the old one from Neptune’s records is said to invite bad luck. Many boat owners perform a lighthearted renaming ceremony involving:

  • removing all traces of the old name.
  • reading a blessing
  • pouring a small amount of champagne into the sea as an offering.

When I bought “Kaikiwi” her name was “dream seeker”. I had held the name “Kaikiwi” for many years in my heart, waiting for the right boat to name her with. I changed the name in Mexico, before I sailed her over. Did I have a ceremony? No. But I did have a long quiet and meditative time as I physically peeled the old name off with a heat gun and proudly applied the new one I had brought with. What does “Kaikiwi” mean? https://sailbluehawaii.com/faqs/

🎩Never leave port on a Friday

One of the oldest maritime superstitions.

The origins are unclear:

  • Friday was traditionally associated with Christ’s crucifixion so some believed it was an unlucky day to begin any major undertaking.
  • Friday was often pay day and leaving port would mean dragging men out of their drinking holes and going to sea with a drunk crew. No good at all.

Historically, however, ships certainly did sail on Fridays when schedules demanded. I sail almost every Friday.

👩 Women on ships—good luck or bad?

This superstition changed over time.

Some believed women aboard distracted the crew and angered the sea.

Others believed women calmed the sea, which is why many ships featured carved female figureheads on the bow to “watch over” the vessel.

I am in favour of the latter, for sure 🙂

and lastly, for now at least, Three sheets to the wind:

“Three sheets to the wind” is one of the most famous expressions to come from sailing, and it has nothing to do with bed sheets.

In nautical language, a sheet is a rope (more accurately, a line) used to control the angle of a sail to the wind. Despite the name, a sheet isn’t part of the sail itself—it’s what the crew uses to trim the sail (change the shape of the sail) for speed and direction.

If a sheet comes loose, the sail begins to flap wildly and loses its ability to drive the boat efficiently.

The phrase “three sheets to the wind” originally described a ship with multiple loose sheets. With several sails no longer under control, the vessel would:

  • Lurch unpredictably from side to side.
  • Yaw off course.
  • Be difficult to steer.
  • Appear unstable and uncoordinated.

Observers noticed this erratic motion resembled the way an intoxicated person staggers while trying to walk.

How drunk is “three sheets to the wind”?

In the 18th and 19th centuries, there was even an informal progression:

  • One sheet to the wind – slightly tipsy.
  • Two sheets to the wind – noticeably drunk.
  • Three sheets to the wind – very drunk.

Today, the phrase simply means extremely intoxicated, and the earlier “one” and “two” sheet versions have largely fallen out of use.

Fun fact

All these expressions are pieces of authentic sailor’s jargon that has survived for centuries. Many common English idioms have similar nautical origins, including:

  • “Learn the ropes” – becoming familiar with a ship’s rigging.
  • “By and large” – describing a ship that could sail both into and away from the wind, later meaning “generally.”
  • “Taken aback” – when the wind suddenly catches the sails from the wrong side, stopping the ship and startling the crew.
  • “Loose cannon” – a cannon that broke free on a rolling ship, becoming a deadly hazard.

All are great examples of how maritime language has shaped everyday English long after most people stopped sailing.

==========================================================

A typical sign, especially on a fishing boat:

*****NO RULES! Bananas on board is OK with me 🙂

Let’s go sailing in Hawaii. I’ll share some more fun boating superstitions.

 capt.gaelyn@sailbluehawaii.com

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

Sailboat Charter in Hawaii

Searching the web, you WILL, of course, find a sailboat charter in Hawaii. What a dream to get out and sail our beautiful islands! There are few charter companies, perhaps only one :-), who offer a REAL sailing experience, hoisting sail at the beginning of your charter and sailing back to the top of the channel at the end. A sailboat charter may well be the highlight of your Hawaii vacation. You’ll leave the chaos of snorkelling with a hundred others to others and appreciate the QUIET and PEACE of 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.

Kaikiwi in “Cruising Compass”:

A few years back, the e-magazine I follow, “Cruising Compass”, reached out to readers to share their boat’s name and story. Kaikiwi and Captain Gaelyn were immediately mentioned and I was thrilled to see Kaikiwi in print! in a magazine! WOW.

A few weeks ago I put out a call for your favourite boat name or the story behind the naming of your boat. I’ve received many interesting stories and I’ll share a few at a time.

Gaelyn Penberthy shared the story of Kaikiwi, her Beneteau 411, pictured above. Gaelyn was born and raised in New Zealand before finding the warmer waters of Hawaii to sail as a charter captain. What does “Kaikiwi mean? “Kai” in Hawaiian means salt water and most know “kiwi” as the global nickname for a New Zealander. A simple and unique boat name that summarizes the experiences of Captain Gaelyn, a true salt water kiwi.

Please continue to share your naming story and send photos of unique boat names you have come across. Send them along to us at cruisingcompass@bwsailing.com.

Choose Sail Blue Hawaii

for your next sailboat/ KAIKIWI charter while here in Hawaii. This time of year is busy with both locals and tourists sailing so get booked now for your desired time and duration. Booking is easy. You will not be disappointed!!

Who’s is your captain?: https://sailbluehawaii.com/about-us/

HAPPY HOLIDAYS

MELE KALIKIMAKA

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)