Private sailing charter in Hawaii

There are many reasons to choose a private sailing charter in Hawaii.

You may never know why you go or how it will change you, but listen to this: last night my sunset cruise (repeat) clients said: last time, after their cruise with me, they went home and took up the boating life! Yep, they went and bought a boat! And have spent the last 4 years cruising the Chesapeake. I was thrilled to hear this. I am not saying after you sail with me you will go buy a boat. After all, the best boat to have is someone else’s. 🙂

What’s so thrilling about a boating lifestyle?

It’s not just romance but you sure can find that. It’s not just freedom but you sure will find that. It’s not just sunsets but you sure will soak them in…maybe even see the green flash. It’s not just rainbows but they will deliver your pot of gold. It’s not just hands on the wheel but YES, the wheel is yours. These are just glimpses of the boating life. Whether you are a sailor or a power boater, at the end of the day, it’s the magic there. You’ve sailed or powered to an anchorage far from everyday life. And this is therapy at its best.

Sign up today for your private sailing charter in Hawaii with Sail Blue Hawaii.

Oahu private sailing charter

While visiting Hawaii, treat yourselves to an Oahu private sailing charter. Getting away from the hustle and bustle of Waikiki and Honolulu, the wind is our engine and the ocean is our playground. I always say the best way to see Waikiki is from a distance. 😎 Everyone agrees.

Where are we going?

“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. Please understand this is not “destination” sailing.  “Destination” is sailing.

Just yesterday the air was so clear, it was magical. We could even see as far as Maui…straight through the channel to Lahaina. That happens once in a blue moon.

Speaking of Lahaina and Maui. Our hearts continue to break as the impacts reach further and deeper, far and wide. Please check out where you can help our families and businesses there. I don’t single out a particular organisation, but there is a list on my website. Please give where you can and PLEASE DO NOT CANCEL YOUR HAWAII VACATION. WE NEED YOU MORE THAN EVER NOW.

When should we 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…✨choose a SUNRISE cruise, a morning or afternoon adventure, or a relaxing SUNSET cruise.✨  It is all good.

Waikiki from a distance:

Email or text Sail Blue Hawaii NOW to sign up for your Oahu private sailing charter

Hawaii Private Sailing Yacht Rental

Today is a great day to call Sail Blue Hawaii for your private sailing charter. Why choose a private sailing charter? In the words of those who have:

“It was sheer joy! Everything was perfect;  the water, the sky, the wind, the fish and the dolphins!!
What a way to end our stay in Hawaii!
Capt Gaelyn, your love of the water made it extra special.”

-Harold & Sheryl, Houston, TX

When should we sail?

Some sail at the beginning of their vacation to sail, often choosing an adventurous day-sail. Others prefer the end of their vacation. What better way to end your vacation than with a relaxing sunset sai?. Those who sail at the begining of their charter have said: “anything after this will be boring”. Those who end their vacation with a private sailing charter have said “sailing with Capt. Gaelyn has been the highlight of our Hawaii vacation.”

Reviews of Sail Blue Hawaii

You can go to my review tab, or see what Yelp and Trip Advisor have to say. Among the words carefully chosen have been:

“part of hidden Hawaii”
“off the beaten track”
“I have never felt so alive”
“memory of a lifetime”
“one of Hawaii’s secret jewels”

“Captain Gaelyn, sailing with you was the highlight of our Hawaiian vacation.”

I have been thinking about Maui so much. I’ve had the privilege to sail to and from, anchor off of, Lahaina many times. One stunning sunrise, on the hook, some years back:

Hawaii Sailing Yacht Rental

Ready for your private Hawaii sailing yacht rental is Kaikiwi, a beautiful 42-ft Beneteau. Kaikiwi is Oahu-based. When sailing in Hawaii, it is important to understand the geography of the islands. Due to the heartbreak that happened on Maui this week, I already have people asking if they should cancel their travel plans. Please don’t. While we reel with the devastation that engulfed Maui, do understand that Oahu is a separate island, 100 miles away. Oahu is physically unaffected by the fires. First the pandemic. Now this. Hawaii needs continued support from those of you who love her, and those who are planning a visit for the first time.

Where do we sail to?

Kaikiwi sails from Oahu’s south (protected) shore, not far from Waikiki. She sails 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. Please understand this is not “destination” sailing.  “Destination” is sailing.

How can we help Maui?

While my platform is to encourage you to sign up for a private sailing charter, today I want to use it for something way more important.

Fire destroyed Lahaina and ravaged other areas of Maui, and thousands of displaced people there are desperate for your kindness. Please do what you can.
Aloha United Way
Aloha United Way has set up the Maui Fire Relief Fund, where donations will go directly to Maui United Way to support Maui victims. 
American Red Cross of Hawaii
The American Red Cross opened five emergency shelters to provide those affected by the Maui wildfires with information, a hot meal, opportunities to charge their phone, pick up relief supplies, and get health services. More information here
Council for Native Hawaiian Advancement
CNHA is matching up to $250,000 in community donations providing critical assistance to families and businesses in Lahaina. 
The Hawaiʻi Community Foundation
The Hawai’i Community Foundation’s Maui Strong Fund was created to provide community resilience with resources for disaster preparedness, response, and recovery. The fund is currently supporting communities affected by the wildfires on Maui. 
The Lahui Foundation
The Lāhui Foundation strives to become a dependable resource for underrepresented and underserved communities here in Hawai’i. They are asking for monetary donations that will go directly to fire recovery efforts for residents of Maui. 
Maui Food Bank
The Maui Food Bank collaborates with various relief organizations to distribute supplies throughout Maui County. 
Maui Mutual Aid Fund
The Maui Mutual Aid is a local effort run by volunteers. They are asking for donations to support vulnerable residents, such as the elderly, those with physical disabilities, renters, and individuals without insurance. More information here
Maui United Way
Maui United Way is accepting donations to its Maui Fire and Disaster Relief fund – all donations will provide direct relief to families and nonprofits directly affected by the Maui Fire Disaster. 

Let’s Go Hawaii Sailing

Kaikiwi sails from Oahu’s south shore. You will embark at Kewalo Basin boat harbor, not far from Waikiki beach hotels. We sail past beautiful coastline in the cobalt blue blue waters of our Pacific. The south shore is the protected side of Oahu: calm and crystal clear, making it the perfect sailing destination.

Why Go Sailing off Oahu?

Common marine wildlife sightings on Oahu are, for example, Hawaiian green sea turtles, “honu”, dolphins, “nai’a”, and humpback whales, “kohola” (in winter season only). In addition, flying fish, “malolo” are some of the critters we may see as we sail about the island.

Incredible Sights While Sailing

Beautiful breathtaking views of Diamond Head are just one of the highlights while sailing Oahu. On clear days, although far in the distance, Molokai and Lanai can sometimes be seen. This is not destination sailing, destination is sailing!

When should we go sailing?

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. 

Kaikiwi happy at anchor.

Call Sail Blue Hawaii TODAY for your private Hawaii sailing charter.