Hawaii Monohull Sailing at its Best

At Sail BLUE Hawaii you will indeed find Hawaii monohull sailing at its best. Look no further. Capt. Gaelyn really SAILS Kaikiwi, your private 42-ft monohull. While other charter companies may motor-sail, or not raise their sails at all, at Sail BLUE Hawaii you will have your sailing experience customised. Your experience can be a gentle, relaxed (for first time/unsure/easy sunset) sail to a more rigorous day-sail. Or, as often happens due to the trade winds, you’ll have a bit of everything. Smiles all around. NO complaints.

Why a Monohull Sailing Charter vs a Catamaran Cruise?

A monohull can give you that real feel of sailing. Wind in your hair. Sounds of the ocean. Waves lapping against the hull. The heel of the boat. Besides which, on Kaikiwi, your charter is private. Catamarans are mostly known for sharing the ride with unknown others, and party-time maitais. Nothing wrong with that. Your concierge will send you to the latter. But be resourceful and keep looking for that off-the-beaten “track” sail like the one offered on Kaikiwi. Occasionally, I get a call from a concierge but mostly they search no further than the catamaran supported by their hotel. Which may lead you to think that that is all there is.

Kaikiwi really does take advantage of Hawaii’s famous tradewinds . Sails are hoisted at the very beginning of your charter. Generally, the catamaran will motor to Diamond Head and then pop a small sail at the bow (front) for an easy downwind sail. The experience on Kaikiwi is all about the sailing and ocean time with friends/family.. I have newbies through to old salts. Both. All. Smiles all around. NO complaints. The catamaran experience is not about the sailing; it’s more about the party and the gathering. Do be aware too, unfortunately, many of the charter monohulls on Oahu give you the same experience as the catamaran…the sailing is often forgotten; motoring is indeed easier.

Each to their own tho. You may well prefer the 2-hull, level catamaran over the one-hull (hence “mono”) heel.

Give the gift of an Hawaii Private Monohull Sail.

What could be a more perfect way to celebrate Dad? A repeat client asked her six-year-old son “What should we do for Dad for Father’s Day?” Without missing a beat, “sailing!!”. A surprise gift of a sail on Kaikiwi rewarded Dad who had just flown in from a business trip and was about to fly back out…30 hours at home. As they got in the car he had no idea where he was going…until he did. Sails were set to a beautiful north-north-east wind. So perfect. The family of three went forward to, what I call, “the best seat in the house”. Yep, smiles all around. NO complaints. A Father’s Day gift to be remembered, perhaps for a lifetime. Thanks Mom.

I use a variety of apps while sailing. My iPad and iPhone are both my technicians. I tracked part of our sail on “Waterspeed” I love this app. I am showing you this screenshot to highlight our average speed…7.9knots!!!… just another awesome sail.                                     

 

Private Hawaii Boat Tour

Sail Blue Hawaii offers private sailing charters in Honolulu aboard the 42-foot Beneteau yacht named Kaikiwi. These custom tours are tailored to your preferences, allowing you to choose the time of day and duration that suits you best. Whether you’re interested in a sunrise sail, a romantic sunset cruise, or a leisurely/ robust day sail, the consistent trade winds in Hawaii ensure a pleasant sailing experience at any time. Custom sailing includes proposals, weddings, life celebrations and ash scatterings; any occasion is a good one to sail with Sail Blue Hawaii.

Highlights of Sail Blue Hawaii’s Private Tours:

  • Customizable Itineraries: You can select from sunrise, morning, afternoon, or sunset sails, depending on your schedule and preferences.​
  • Comfortable Yacht: The Kaikiwi features both covered (lots of shade) and open-air seating, along with an onboard restroom, ensuring comfort.​
  • Variety of Experiences: Popular options include coastline sightseeing, Friday night fireworks viewing, and special events like birthday celebrations and anniversaries.
  • Experienced Captain: Captain Gaelyn brings extensive knowledge and a passion for sailing, ensuring a safe and enjoyable experience.​ (https://sailbluehawaii.com/about-us/)
  • Affordable Pricing: Private charters are competitively priced, often comparable to shared tours, offering a more personalized and intimate experience.

Booking Information:

  • Contact: Email: capt.gaelyn@sailbluehawaii.com​ is the best way to connect.
  • Phone: (808) 347-0235​….but TEXT is BEST
  • Location: Kewalo Basin Harbor, 1025 Ala Moana Blvd, Honolulu, HI 96814​

If you need assistance with booking or have specific questions about the tours, feel free to ask!. If captain’s hands are on the wheel, a call to personal line (808) 347-0235 will have a slower response time than a text.

DON’T DREAM YOUR LIFE: LIVE YOUR DREAM

Hawaii Private Sailboat Tour for the Whole Family

It’s the summer holidays already! Sail Blue Hawaii offers private sailboat tours for the whole family. It doesn’t matter how young or how old. This may well be the best family “tour” of your HI vacation.

private sailing fun for the whole family

FAQ: “Do you REALLY sail or do you just motor around?”

At Sail Blue Hawaii we SAIL. Due to harbour rules, we cannot hoist sail within the marina but, once we are clear of the # 1 buoy at the top of the channel, the sails go up. With Sail Blue Hawaii, unlike other companies, we HOIST SAIL at the BEGINNING of your charter; the engine is turned off until we need it again at the end of your charter!!

YES, WE SAIL THE ENTIRE CHARTER!!

Even if this is your first time sailing, Capt. Gaelyn customises your sail to your wants and needs. In other words, you can be given a gentle sail or, for those with more experience, an exciting full-sail “heel on” adventure; this is monohull sailing at its best!. All choices take advantage of the consistent and refreshing trade winds that sweep across the Hawaiian Islands.

FAQ: When can we sail?

Delight in pure trade wind sailing any time of day for as many hours as you want. Our islands are almost consistently graced with trade winds so any time is a good time to go sailing…✨✨✨magical SUNRISE cruise, full-sail morning and afternoon, romantic/ peaceful SUNSET cruise.✨✨✨ It is all good. 


these keiki and mom know how to hang loose!

Whether your family members are seasoned (monohull) sailors or those who want to experience the thrill of sailing for the first time, a Hawaii day-sail is an excellent way to connect with our ocean, embrace the trade winds, and create lasting memories of your time in paradise.

Kiss the tour bus goodbye. This is the ride and experience of your lives. Two + hours of pure exhilaration with the wind and waves off Waikiki as your engine. 

Choose Sail Blue Hawaii for your Hawaii private sailboat tour for the whole family TODAY!

Private Sailing Charter Hawaii

Because this is a custom PRIVATE sailing charter, 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. 

Dreams Come True in Blue Hawaii

Sail Blue Hawaii offers private sailing charters for all ages. There is no limit to children’s ages, nor elderly, as long as the latter is mobile and agile.

I can’t say enough good things about the people who find my website and sign up to sail with me. It’s a delight for me to spend Kaikiwi time with you. Whether you have never sailed before, or even perhaps never been on a boat, OR you are a seasoned sailor, I taper the sail to your comfort and/ or (:-)) your excitement. Because we are gifted with tradewinds, I can “wind it up” or “wind it down”, customised just for you and your expectations. For a more adventurous sail do choose a day-sail when we sail full sail. Sunset cruising is all about kicking back and relaxing, perhaps enjoying a cocktail. I sail with a lighter sail plan than during the day unless otherwise requested. Because our sunsets don’t tend to linger, we are back at the dock very soon after sunset. If you decide while we are out there that you would like extend your cruise to see city lights, by one half hour or more, can do. This is common, especially on spectacular evenings. No need to decide until then.

sunrise cruise

“Years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bow lines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”
-Mark Twain

Email with your charter request today. Any type of request is encouraged: proposal, wedding, ash scattering, life celebration, sailing lesson OR: you need no reason at all other than to enjoy ocean time with close ones, with the wind as your engine, and the sounds of sailing. It’s magic.

We are priced right to get you out there. I look forward to spending Kaikiwi time with you.

With warm aloha, Capt. Gaelyn (808) 347-0235 

Visit https://sailbluehawaii.com for your HI sailing vacation

capt.gaelyn@sailbluehawaii.com

“There is nothing, absolutely nothing, half so much worth doing as simply messing around in boats”.  – –Kenneth Grahame

Private Sailing Charter Hawaii

Sail Blue Hawaii wishes you and yours a HAPPY 2025. If you vacation to Hawaii, make sure to book a private sailing charter with us. You will NOT be disappointed. It may well be the highlight of your HI vacation.

More next year!. Tune in then.

I look forward to spending Kaikiwi time with you.

With warm aloha,

Capt. Gaelyn

(808) 347-0235 

Visit https://sailbluehawaii.com for your HI sailing vacation

“There is nothing, absolutely nothing, half so much worth doing as simply messing around in boats”. 

Kenneth Grahame