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.

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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

Hawaii Monohull Sailing at its Best

At Sail BLUE Hawaii you will indeed find Hawaii monohull sailing at its best. Look no further. Capt. Gaelyn really SAILS Kaikiwi, your private 42-ft monohull. While other charter companies may motor-sail, or not raise their sails at all, at Sail BLUE Hawaii you will have your sailing experience customised. Your experience can be a gentle, relaxed (for first time/unsure/easy sunset) sail to a more rigorous day-sail. Or, as often happens due to the trade winds, you’ll have a bit of everything. Smiles all around. NO complaints.

Why a Monohull Sailing Charter vs a Catamaran Cruise?

A monohull can give you that real feel of sailing. Wind in your hair. Sounds of the ocean. Waves lapping against the hull. The heel of the boat. Besides which, on Kaikiwi, your charter is private. Catamarans are mostly known for sharing the ride with unknown others, and party-time maitais. Nothing wrong with that. Your concierge will send you to the latter. But be resourceful and keep looking for that off-the-beaten “track” sail like the one offered on Kaikiwi. Occasionally, I get a call from a concierge but mostly they search no further than the catamaran supported by their hotel. Which may lead you to think that that is all there is.

Kaikiwi really does take advantage of Hawaii’s famous tradewinds . Sails are hoisted at the very beginning of your charter. Generally, the catamaran will motor to Diamond Head and then pop a small sail at the bow (front) for an easy downwind sail. The experience on Kaikiwi is all about the sailing and ocean time with friends/family.. I have newbies through to old salts. Both. All. Smiles all around. NO complaints. The catamaran experience is not about the sailing; it’s more about the party and the gathering. Do be aware too, unfortunately, many of the charter monohulls on Oahu give you the same experience as the catamaran…the sailing is often forgotten; motoring is indeed easier.

Each to their own tho. You may well prefer the 2-hull, level catamaran over the one-hull (hence “mono”) heel.

Give the gift of an Hawaii Private Monohull Sail.

What could be a more perfect way to celebrate Dad? A repeat client asked her six-year-old son “What should we do for Dad for Father’s Day?” Without missing a beat, “sailing!!”. A surprise gift of a sail on Kaikiwi rewarded Dad who had just flown in from a business trip and was about to fly back out…30 hours at home. As they got in the car he had no idea where he was going…until he did. Sails were set to a beautiful north-north-east wind. So perfect. The family of three went forward to, what I call, “the best seat in the house”. Yep, smiles all around. NO complaints. A Father’s Day gift to be remembered, perhaps for a lifetime. Thanks Mom.

I use a variety of apps while sailing. My iPad and iPhone are both my technicians. I tracked part of our sail on “Waterspeed” I love this app. I am showing you this screenshot to highlight our average speed…7.9knots!!!… just another awesome sail.                                     

 

The Best Sailing Tour in Hawaii

Hawaii is one of the best places in the world to go sailing—warm trade winds, clear water, dolphins, turtles, and dramatic coastlines on every island. Whether you’ve never sailed before or you are an “old salt”, the best Oahu sailing tour is, without doubt, the one Sail Blue Hawaii offers: an authentic sailing experience. Whether you choose a full-sail day-sail, sunset romance, sunrise cruising, sailing “just because”, “no-reason” sailing, this is REAL sailing; custom PRIVATE sailing. You get to choose; it’s entirely up to you, whatever your vibe is. (Do understand the use of “you” throughout this post refers to “you and yours”.)

What is an authentic sailing experience?

Do we really sail? YES! with Sail Blue HI, unlike other “sailing charter” companies who boast “sailing”, sails are hoisted once clear of the channel and are doused (“struck”) around the same salty place at the end of your sailing charter. Same is true even on a romantic sunset cruise when the sail plan is lighter to align with the relaxing sunset-hour vibe.

Why your sailing tour in Hawaii is so special

Let me count the ways LOL:

  • It’s super easy to get to Kewalo Basin (Honolulu) where your 42-ft Beneteau “KAIKIWI”, the best-kept charter boat in the islands, awaits YOU.
  • This is a PRIVATE sail…that on its own is so very very special. Leave the Waikiki crowds behind or on that catamaran following you out the channel. Those folks on the crowded cat are jealous of your beautiful space.
  • Whether a full-sail day-sail, a sunrise sail, a special event sail, or an evening sunset sail, it is a perfect, low-effort sailing experience for you. What a vacation!

But that is not all:

  • NO engine; NO exhaust fumes. Just the beautiful, peaceful sounds of waves lapping against the hull and the wind in the sails. What we all need today is this kind of peace. You and yours deserve this pleasure. Yes you do!

Skip the lines. Choose the best sailing tour in Hawaii. Dive into your sailing adventure NOW. Or book for next week, next month. It may well be the highlight of your HI vacation.

Sail Hawaii’s Best

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having doused the sails at the finish of another fabulous sailing adventure… nobody wants it to end

Sail Hawaii’s Best…….. with Sail Blue Hawaii’s private sailing charters in Honolulu aboard the 42-foot Beneteau yacht named Kaikiwi. These custom tours and adventures 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 day sail, the consistent trade winds in Hawaii ensure a pleasant sailing experience at any time.​

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 and open-air seating, along with an onboard restroom, ensuring a comfortable journey .
  • Variety of Experiences: Popular options include coastline sightseeing, Friday night fireworks viewing, and special events like proposals, weddings, birthdays and life memorials.​
  • Experienced Captain: Captain Gaelyn brings extensive knowledge and a passion for sailing, ensuring a safe and enjoyable experience. Read about her:​ https://sailbluehawaii.com/about-us/
  • Affordable Pricing: Private charters are competitively priced, often comparable to shared tours. But a choice of PRIVATE offers a more personalized and quality experience that could well be the highlight of your HI vacation.!!

Booking Information:

Weekends and holidays fill quickly so plan ahead and book today.

  • Contact: Email: capt.gaelyn@sailbluehawaii.com
  • Phone: (808) 347-0235 ​
  • Location: Kewalo Basin Harbor, Slip C30, 1025 Ala Moana Blvd, Honolulu, HI 96814​

For more details and to view available tours and sailing adventures, visit our ocean activities page:  https://sailbluehawaii.com/hawaii-ocean-activities/

If you need assistance with booking or have specific questions, do ask!

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easy sunset cruising

Start Keiki Young on Hawaii Private Sailing Charters

A potential client the other day asked about the child age limit for a Hawaii private sailing charter. When I said “there is no limit” he signed up immediately for a day-sail, 6 family members on board. The keiki had a blast and, with life jackets on, with an adult, the little ones gleefully sat on Kaikiwi’s forward deck. “The best seat in the house”, I call it. Sometimes you get wet, which often pumps the kids to laugh even more.

The Foredeck is not just for Keiki

Hawaii private sailing charters cover every type of request: proposal, saying “I Do”, sunrise cruise, adventure day-sail, (romantic) sunset cruise, sailing lessons, life celebrations and ash scattering. 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. Create your own adventure, any day, any time of day.

Keiki having a thumbs up moment…one of many

Hawaii Sailing at it’s Best: with the Whole Family

The easiest way to proceed is to email Sail Blue Hawaii (captain probably has hands on the wheel and can’t chat right now). We are priced right to get you out there!    Pricing depends on number in your group, duration desired, etc, so email for your personalised quote.  Indicate the number in your party, age of young ones, what kind of charter you want and when you are traveling. 

Dreams Come True in BLUE Hawaii:

This private sailing family experience may well be the highlight of your Hawaii vacation. You’ll love watching your kids respond to the sailing and the ocean; especially if they see wild life. A highlight for sure! Book now for your Hawaii private sailing charter.

On a more personal note:

Brian G, if you are reading this , please reach out. In 2016, your lovely little one became my first mate. Gosh, she is a young lady already.

capt.gaelyn@sailbluehawaii.com