Hawaii sailing lesson

Help set the sails, and take the helm if you like, as you learn the “ropes” of sailing. In your Hawaii sailing lesson, the first thing you learn: they are not ropes.  They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. Your Hawaii sailing lesson is for all levels of sailing experience.

“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”

Sailing is clouded in romance. Many people dream of a life of sailing and the adventure of perhaps one day sailing to distant shores. The reality is often different than the dream and this is important to understand.

So, before you go buy that boat, come sailing with me and begin or continue learning the skills that will gain you confidence and give you a whole bunch of joy as you succeed. Your time “out there” will also give you a taste of what true blue-water sailing is all about.

You don’t have to have the dream of distant shores to sign up for a lesson…you can begin by taking up sailing as a day-hobby.

Do you have someone in your life who has always had an itch to try sailing but has never had the opportunity? Buy him/her a gift certificate for a private sailing lesson. It will be the best present they have ever had! It is a WOW!!

Whatever your goal is, the lesson will fit.

Even if you are the only one who wants to learn and you don’t wish to come alone, your friends/ family are welcome on board and can enjoy the sail while you learn.

So, whether your dream is to sail the Waikiki coast or beyond that horizon (a multi-day charter is perfect for introducing you to all aspects of sailing and living aboard), your personalized Hawaii sailing lesson is waiting for you!

Having fun!! Perhaps it doesn’t look like 25 knots but those on board know very well that it is.

Hawaii private sailing charter

Your Hawaii private sailing charter 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. 

A private sunrise sail to remember

It was a beautiful chilly morning when we left the dock before sunrise. The sky colours changed every minute, it seemed, as we sailed towards Diamond Head. The sunrise clouds coloured every point on the compass.

Along the way, in the precious still of the morning, we dropped sail to scatter ashes of their loved one, flowers following. It was magical, peaceful and a tender way to start the day.

Get in touch with Sail Blue Hawaii for your private sailing charter. Your private boat tour will include magic that you couldn’t even anticipate.

Hawaii ash scattering/ life celebration

As captain of your private sail boat, it is an honour 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. When all is done, an easy down-wind sail brings your 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.

Hawaii Marriage Proposal

The Hawaiian islands are known for their romance. So, what could be more perfect than saying “I will” aboard your own private yacht at sunset. Yes, your Hawaii marriage proposal will guarantee she says “yes.”

Saying “yes” is just the beginning

May the love you share today be just as strong every day in the years to come. You will look back on this evening as not just the highlight of your Hawaii vacation, but the highlight of your lives. Your private Hawaii marriage proposal will set the tone of your lives together as you sail off into the sunset.

Hawaii multi-day sailing charter

Pre-covid, a multi-day sailing charter in Hawaii was the best adventure to sign up for. It still looks like a while before I have the opportunity to safety re-start these amazing sailing adventures. In the meantime, do book a private sailing charter for the day. A day-sail can be just the adventure you want.

Why chose a multi-day sailing charter?

“DON’T DREAM YOUR LIFE, LIVE YOUR DREAM”

“So, where are we going?”

“We are going sailing.”

… with island-stops and remote anchorages, sailing Oahu and Maui county from home-base, Oahu.  Where we go between day-one and journey’s end will depend on wind and weather. If you want to take time to have a day here and there to just hang out “on the hook” or at the beach, we can also accommodate this.

To understand Hawaii sailing is to understand her geography:  remote islands in the middle of the Pacific Ocean, shallow channels between these islands, high mountain peaks on each of these islands. This combination can brew very windy and high-sea-state conditions, especially in the channels.

Please understand this is NOT A CRUISE. IT IS adventure sailing…some call it “extreme” sailing…from easy light air and downwind runs to upwind sailing in strong winds and big seas.  Yes, on some days, conditions will be challenging. Rest assured: your USCG-licensed captain has sailed these waters for years and the boat is a sturdy workhorse in these conditions. This is blue water sailing at its best as only Hawaii can offer.

A multi-day charter in the Hawaiian Islands is perfect for adult sailors who have some ocean in their veins.  That being said, if you are sailing as a newbie, all you need is a sense of adventure, love of the outdoors and “roughing it”, and your cheery disposition.

Inter-island trips are offered as multi-day sailing vacations for adults only, (max four adults) not ferry services.  In other words, if all you want is a quick delivery from one island to another, this is not offered.  While land-time can be arranged, please understand that your destinations are weather-permitting and it is best to keep the sailing vacation schedule as loose as possible. Land-based activities can be arranged within an extended trip. Our inter-island sailing grounds are off Oahu, Molokai, Lanai and Maui.  They do not include passage to Big Island or Kauai.

sailing Oahu’s west end

Overnight adventures (minimum 2 nights, 3 days) are also available, Oahu-based. This is a wonderful way to enjoy tradewind sailing if the idea of channel crossing sounds more than your idea of “fun”.