Hawaii proposal Archives - Private Sailing Charters, Honolulu, Oahu, Hawaii

November 8, 2026November 9, 2026

A Sunrise Cruise to Remember

Your birthday is a great excuse to get out of bed early and experience our Diamond Head Sunrise Cruise. Greet the new day aboard your private boat charter “Kaikiwi“. This is not only a great photo opportunity but something special to remember on your vacation in Honolulu. You are a local? That’s even better. Call the boss and take the morning to the water. Certainly not everyone is an early riser but the view of sunrise over Diamond Head is well worth the effort. It will be a sunrise cruise to remember.

Say “YES” on your Private Yacht at Sunrise

What better way to start the day than to ask your beloved if they will. There is no way they can say NO in this glorious morning setting.

Sunrise: some say it is the best time to be on the water

Perhaps 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. A sunrise sail in Hawaii is a magical and serene experience. The Hawaiian islands are renowned for their breathtaking sunrises, and a sunrise sail offers an unforgettable opportunity to embrace the beginning of a new day in paradise.

Why Choose Sunrise to Sail with Sail Blue Hawaii?

Sailing a sunrise cruise with Sail Blue Hawaii gives you a beautiful, private, peaceful start to the day:

Private and Personal: The charter is exclusive to your group on board the 42-foot Beneteau 411 Kaikiwi, so you skip the crowded tour buses.
Stunning Scenery: Watch the morning light hit Diamond Head and see early-morning Waikiki from a distance while hearing the surf break at Waikiki.
Customizable Experience: Captain Gaelyn Penberthy tailors the trip to your pace, whether you want a quiet, romantic morning, a special occasion like an anniversary or proposal, or a hands-on Sunrise Sailing Lesson.
Marine Life: Early-morning trips offer a chance to spot local wildlife like sea turtles, dolphins, or flying fish. We are moving into whale season…can you imagine seeing a whale breach this time of day?

All sailors know what “red sky in the morning” means. For those that don’t, let me explain: It means awesome photography and a sunrise cruise to remember.

SailBlueHawaii.com

April 2, 2026April 2, 2026

Hawaii Sunrise Sailing Charter

Nothing beats the morning peace and beauty that a Hawaii sunrise sailing charter gives. Because this is custom sailing, we can, of course, sail any time of day you want and whatever length of time you wish. But if you choose sunrise, your day begins with magic. The rest of your day becomes just a breeze.

When is a good time to go sailing?

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 / easy SUNSET.✨ It is all good. Choosing a sunrise cruise for a special occasion such as a birthday, anniversary, even saying “I DO”, will make that day and that year a highlight, remembered for a lifetime.

So, kiss the tour bus goodbye. Take the ride of your life with the wind off Waikiki as your engine, hearing the lapping of gentle waves on the boat’s hull.

Email now to book your Hawaii (SUNRISE) sailing charter:

January 2, 2026January 3, 2026

Hawaii Private Sailing “off the beaten track”

Set the tone (adventure, romance, fast sailing, slow easy sailing…) for your New Year and book a Hawaii private sailing charter A client this week (I am always interested, of course, how customers navigate to my site) said he had searched ” ‘un-touristy’ sailing charter”. ha ha. I love that Sail Blue Hawaii is thought of as different, AND un-touristy! Indeed, Sail Blue Hawaii does offer a different ocean experience than the many many catamaran tours (you’ll find online) where you “sail” with 59 of your closest friends. A novel approach another customer took to find exactly what she wanted was by the use of A.I “CoPilot”. Her request was immediately answered with the details sought and the suggestion of: “email capt.gaelyn@sailbluehawaii.com”. Do just that and you’ll find that we are priced right to get you out there.

5 best ideas that makes Sail Blue Hawaii unique and different

We raise sails at the beginning of your charter and sail the entire time. For Hawaii, where many others motor or motor-sail, this is a unique treat. Sailors love this, as does everyone else…newbies too. Welcome aboard a true sailing charter.
You have a uniquely private sailing charter. This means it’s only you and your family group. Perfect for romantic couples and celebrations too. No flu-bugs here.
This is custom sailing. Unlike other companies who have a strict timetable, you can sail any time of day you want and whatever length of time you wish. No one else on island offers this: you are limited to their schedule. Our islands are mostly graced with consistent trade winds so any time is a good time to go sailing.
Sailing lessons are offered for those wanting the taste. When else could one have the opportunity to put their hands on the wheel of a beautiful pricey yacht? Certainly no one else in Hawaii offers sailing lessons without you first signing up for the rigid ASA program on sub-par sailboats.
You get to bring your own food and beverage. With today’s dietary needs, nothing is worse than having a pre-catered expensive menu, with foods you cannot eat, and having that cost hidden in your charter fee. You will appreciate this too if you have keiki.

HAVE A HAPPY NEW YEAR

by setting sail with Sail Blue Hawaii. You can navigate to the website with tag “un-touristy” sailing and/or using A.I. with your unique request. You’ll leave the chaos of snorkeling with a hundred others to others and appreciate the QUIET and PEACE of true 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. You will not be disappointed with your choice of Hawaii’s best private sailing “off the beaten track”.

NO RULES! Bananas on board is OK with me 🙂

DON’T DREAM YOUR LIFE, LIVE YOUR DREAM

October 17, 2025October 17, 2025

Hawaii’s BEST Private Sailing Charter

Choose Hawaii’s BEST private sailing charter, Sail Blue Hawaii. Any occasion is a great one to get out sailing on the Hawaiian waters. Enjoy some relaxing and refreshing ocean time here 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, life celebrations and custom adventures await.

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

another amazing Hawaii sunset; it can take your breath away

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

September 29, 2025

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

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.
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.
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.
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.
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.