private yacht charter Archives - Private Sailing Charters, Honolulu, Oahu, Hawaii

February 13, 2026February 14, 2026

5 BEST HONOLULU PRIVATE SAILING CHARTER IDEAS

Honolulu TRADEWIND sailing, where any time is a good time to be on the water. Highlight your Hawaii vacation aboard a sailboat on our beautiful cobalt blue Pacific Ocean. Here is our recommendation on SOME OF the MANY 5 best Honolulu private sailing charter ideas.

Private Sailing ideas; Waikiki, Hawaii

A tradewind day-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 tradewinds so any time of day is a good time to go sailing…sunrise, morning, afternoon, or sunset. IT’S ALL GOOD!
A sail to take in the beautiful views of Oahu and beyond. Outstanding views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen. This is not “destination” sailing. “Destination” is sailing.
A private day-sail to capture sightings of marine life. “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. (I believe we did see a mermaid one time; sh sh sh……………)
Birthday celebrations at sea. What better way to celebrate that special day for that special someone than aboard a private yacht charter in Honolulu?
Corporate Events. Celebrate with the team onboard a sailing yacht off the Honolulu coast. How better to raise morale and reward them for a job well done?

Many many ideas for your custom cruise are accepted and sailed

https://youtube.com/shorts/PBDlY4_DZnA

This was one beautiful day to sail around Diamond Head into Maunalua Bay. My guests got the last good sailing in before Oahu was rocked by a decent winter storm. Not all Sou’Westers are bad 😎. We were lucky. What a peaceful time.

View other movies on Sail Blue Hawaii’s youtube channel

When should we book?

NOW!! Booking ahead of time is a good idea just to secure your sail. Today is also a perfect day for a HONOLULU PRIVATE SAILING CHARTER; last-minute requests can sometimes be accommodated but don’t count on it; and, ANY occasion is a good one to get out on the water with Sail BLUE Hawaii.

a rare view while on a HI day-sail:

Koko Crater

Email with your idea for your Honolulu Private Sailing Charter sail. Your experience aboard may well be the highlight of your HI vacation

Locals too! Take a day off and let’s go sailing capt.gaelyn@sailbluehawaii.com

The Horizon is NO Limit

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.

February 18, 2024

Hawaii Proposal at Sea

Definition of romance: chartering your private yacht to propose to your loved one while in Hawaii. Imagine saying “YES” while sailing into the sunset.

Sail Sunset on Valentine’s Day

This Valentine’s Day was a highlight for me. I have been running private charters for many years now but this one stands out. The young couple, delighted in each other, chose to spend their time on the forward deck…what I call the “best seat in the house”. Not long into our sunset sail, a whale breeched, some distance from us but still out-of-this-world spectacular. We spent the two hours enjoying 2 whale groups as they swam and played in Mamala Bay. Honolulu, Hawaii. Humpback whale sighting rules are strict here: keep a minimum 100 yard distance and do not change direction to follow them. No worries! We just sailed our track and the whales theirs and the show went on. The couple I took sailing earlier in the day have been thrilled daily by whale sightings from their Waikiki lanai. But there is NOTHING better than seeing them from your Hawaii private yacht.

Dolphins too!

Yep. As if the humpbacks weren’t thrilling enough, the Hawaiian spinner dolphins came out to play. Usually in my sailing area, dolphins cruise by around 10 in the morning. So imagine the thrill of this huge pod swimming in Kaikiwi’s bow wake, frolicking and spinning all around us. WOW! As sunset came on, he asked, she said “YES”! How could you not after a show like this?

Sail Blue Hawaii

Call today for your Hawaii proposal at sea. It will stay with you for your lifetime.

August 15, 2022September 4, 2022

Private Sailing Charter in Hawaii.

When you book your private sailing charter while vacationing in Hawaii it may well be the highlight of your vacation. It is astonishing how many times my clients have said that to me. That is thrilling. It is exactly why I have worked so hard to give people the best-kept charter vessel in the islands, AND the best private sailing charter experience. That was my goal when I set up up Sail Blue Hawaii LLC.

“This is the best time I have had in my entire life.”
-Kaelyn, age 7, CA

Why choose a private sailing charter?

There are so many reasons, but let me name a few:

CoVid is still around. Your captain is vaccinated and boosted. How better to keep you and your loved ones safe. When you sail on “Kaikiwi”, a 42-ft Beneteau, you will feel so safe especially when you see the over-crowded catamarans.
delight in pure trade wind sailing any time of day for as many hours as you want.
whale sail. In winter, humpbacks are Hawaii’s most famous tourists, making their annual 3,500 mile trip from Alaska to the islands each December through April. We’ll set sail and hope to find these gentle leviathans.
birthday parties
corporate fun(ctions)
very popular: summer only; Friday night pau hana fireworks cruise. Combine this with sunset and you have the perfect cruise.
for romantics: sunset cruise: a beautiful time of day to be on the water.
maybe 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.
choose the one night of the month (or, the “blue moon” second night of the month) to sail from sunset to full moon. It is truly magical to see the full moon rise over Diamond Head after sailing into the sunset. Click moon phases to see full moon calendar.
when the moon is close to its new phase, we have fabulous star-gazing. Set sail for sunset and a night sail. In winter months, the iconic Southern Cross can be seen.
proposal: how more romantic can you get when you propose to your loved one while sailing into the sunset?
weddings for romantics: there’s nothing more special than saying “I do” under a tropical sky while sailing into the sunset. Your captain will marry you with a personalized service on your own private yacht.
renewal of vows: what a “wow” it is to say those vows again, to remember and re-ignite!
sailing lessons: Help set the sails and take the helm if you like as you learn the “ropes” of sailing. The first thing you learn: they are not ropes. They are “lines.” Captain Gaelyn will assist you to build your skills and confidence. For all levels of sailing experience.
memorials, ash scatterings and life celebrations

February 27, 2022February 27, 2022

Hawaii private sailing charter

Any occasion is a great one to get out sailing on Hawaiian waters to enjoy some relaxing and refreshing ocean time. Especially here in Hawaii. 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 certainly the private yacht charter, weddings, anniversaries and sunset sailing cruises. In addition, sailing lessons, birthdays and corporate adventures await.

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

Tag: private yacht charter