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.

A Perfect Hawaii Sailing Charter

You have just navigated your way to Sail Blue Hawaii LLC and your perfect Hawaii sailing charter. “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. Beautiful views of Oahu, famous Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen.

Talking about Navigation…

I was sailing with a family the other day and happened to mention that new boats are sold without a compass. Astounding, I know. They couldn’t believe it either. Well then, how the heck to you get from A to B? Everything today is electronic, from your charts to your navigation systems. Hence…no (“need for a”) compass. It’s like kids growing up and not knowing how to tie their shoe laces or even what a shoe lace is. In many ways, the young generations can be envied for what is at their fingertips. But it is very sad the day the compass dies, along with the paper chart (which cannot be purchased any more. If you really must have one, you have to special order it.) I love to have my hands and eyes all over paper charts. I love to use and teach with my compass. I am hanging on.

Kaikiwi’s compass can double as an inclinometer

A six-year-old, looking at my compass, asked if it is my “tip meter”. Sweet.

“The Riddle of the Compass”

is an intriguing book by Amir D. Aczel. The story of the compass is shrouded in mystery and myth, yet most will agree it begins around the time of the birth of Christ in ancient China. It is an historical and scientific exploration of the magnetic compass, arguing it was the single most transformative invention after the wheel. The book traces the device’s evolution from ancient Chinese divination tools to its revolutionary impact on global navigation, commerce, and the Age of Exploration. Have it read to you here: https://www.youtube.com/watch?v=Hvybyr-du5w or buy it from your local book store.

I found this to be a gripping read…truly.

How can you learn more about Sailing and Navigation et al, in real time?

Whether a sailing lesson or a casual private sailing charter, Sail Blue Hawaii can customise your special sailing request. It’s while sailing you can ask all questions…a far better way to learn than thru AI. AI is not even close.

Navigate your way to Sail Blue Hawaii LLC and your perfect Hawaii sailing charter.

A perfect close-reach Hawaii sailing charter

One particular day, recently, the wind was just a little south of east, creating the perfect close-reach Hawaiian sailing charter. My clients loved the ride: “we’ve NEVER been this far out before…the island is getting small”. The video actually shows how large Oahu is, and we still couldn’t get the west end in the frame. Have to sail even further south for that!

How long should we sail?

Unfortunately, this particular day, at the above turn-around, we realised we had not planned well enough for destination Tahiti. Another day, perhaps.

What will we see?

With a keen eye, we could faintly see the nearest island, Moloka’i. There was too much moisture in the air to see it crisply.

We were blessed with a sighting of a mum, calf and escort humpback whale swimming west, home to Alaska.

Closer to shore, a lone honu (green sea turtle) raised its lazy head and gave us an eyeful of eyeball.

All in all it was a brilliant 4-hr sail. A perfect amount of time for all.

Do email to schedule your perfect close-reach Hawaiian sailing charter (or whatever the wind dishes up):

YES, we really do sail.

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

  1. 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!
  2. 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.
  3. 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……………)
  4. Birthday celebrations at sea. What better way to celebrate that special day for that special someone than aboard a private yacht charter in Honolulu?
  5. 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

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?

a rare view while on a HI day-sail:

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

Private Charter Oahu

Vacationing in Hawaii MUST include a private charter while on Oahu. “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. Beautiful views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen.

Should we book at the beginning or end of our vacation?

Of course, this is a personal preference. Some choose day-one to get over their jet lag and, before they left home, already booked a private sailing charter with Sail Blue Hawaii for day-two. This is perfect. You can sit back and relax, taking in the stunning sights of ocean and land. Having this “do-nothing” second day of vacation will pump you with the excitement and wonder that is Hawaii, while adjusting to Hawaiian time.

Others choose the last day for their private Oahu charter. Before they leave home they book, most commonly, a beautiful and unforgettable sunset cruise. This highlight is keeping them warm and happy as they pack their bags for the cold flight home. An adventurous day-sail is also a common option. Photos and videos of this last day on Kaikiwi, their private Oahu sailboat, keep their memories flowing, certainly taking much HI home with them.

Better, yet. Sail both :-):

“Our first sail was so exceptional that I texted her just a few days later to see if we could go out again before returning home. Our second sail was even more spectacular than the first. The trade winds were perfect, the scenery was breathtaking, and once again, Captain Gaelyn made the entire experience educational, comfortable, and memorable, including seeing sea turtles and dolphins in the distance. Starting and ending our vacation on the water with her was truly special, and it’s an experience I will carry with me forever. I cannot recommend Sail Blue Hawaii enough, especially for anyone who wants to experience the beauty and thrill of true ocean sailing. I will absolutely be referring all of my sailing friends to Captain Gaelyn and Kaikiwi Sail Blue Hawaii. Captain Gaelyn, thank you for sharing KaiKiwi with us!” you are so welcome!!!

So there you have it ! Book your private charter Oahu today with Sail Blue Hawaii. Pre-booking before you leave home, ensures the charter day and time of your choice…beginning, ending, middling…or all THREE! LOL The season ahead is busy..time slots fill fast so do pre-book a week or two out.*** Local or tourist…set your holiday season with the gift of Sail Blue Hawaii’s private charter Oahu … pleasure guaranteed!

(***last-minute bookings are of course also accommodated, room permitting)