The Best Sailing Tour in Hawaii

Hawaii is one of the best places in the world to go sailing—warm trade winds, clear water, dolphins, turtles, and dramatic coastlines on every island. Whether you’ve never sailed before or you are an “old salt”, the best Oahu sailing tour is, without doubt, the one Sail Blue Hawaii offers: an authentic sailing experience. Whether you choose a full-sail day-sail, sunset romance, sunrise cruising, sailing “just because”, “no-reason” sailing, this is REAL sailing; custom PRIVATE sailing. You get to choose; it’s entirely up to you, whatever your vibe is. (Do understand the use of “you” throughout this post refers to “you and yours”.)

What is an authentic sailing experience?

Do we really sail? YES! with Sail Blue HI, unlike other “sailing charter” companies who boast “sailing”, sails are hoisted once clear of the channel and are doused (“struck”) around the same salty place at the end of your sailing charter. Same is true even on a romantic sunset cruise when the sail plan is lighter to align with the relaxing sunset-hour vibe.

Why your sailing tour in Hawaii is so special

Let me count the ways LOL:

  • It’s super easy to get to Kewalo Basin (Honolulu) where your 42-ft Beneteau “KAIKIWI”, the best-kept charter boat in the islands, awaits YOU.
  • This is a PRIVATE sail…that on its own is so very very special. Leave the Waikiki crowds behind or on that catamaran following you out the channel. Those folks on the crowded cat are jealous of your beautiful space.
  • Whether a full-sail day-sail, a sunrise sail, a special event sail, or an evening sunset sail, it is a perfect, low-effort sailing experience for you. What a vacation!

But that is not all:

  • NO engine; NO exhaust fumes. Just the beautiful, peaceful sounds of waves lapping against the hull and the wind in the sails. What we all need today is this kind of peace. You and yours deserve this pleasure. Yes you do!

Skip the lines. Choose the best sailing tour in Hawaii. Dive into your sailing adventure NOW. Or book for next week, next month. It may well be the highlight of your HI vacation.

Sail Hawaii’s Best

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having doused the sails at the finish of another fabulous sailing adventure… nobody wants it to end

Sail Hawaii’s Best…….. with Sail Blue Hawaii’s private sailing charters in Honolulu aboard the 42-foot Beneteau yacht named Kaikiwi. These custom tours and adventures 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 day sail, the consistent trade winds in Hawaii ensure a pleasant sailing experience at any time.​

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 and open-air seating, along with an onboard restroom, ensuring a comfortable journey .
  • Variety of Experiences: Popular options include coastline sightseeing, Friday night fireworks viewing, and special events like proposals, weddings, birthdays and life memorials.​
  • Experienced Captain: Captain Gaelyn brings extensive knowledge and a passion for sailing, ensuring a safe and enjoyable experience. Read about her:​ https://www.sailbluehawaii.com/about-us/
  • Affordable Pricing: Private charters are competitively priced, often comparable to shared tours. But a choice of PRIVATE offers a more personalized and quality experience that could well be the highlight of your HI vacation.!!

Booking Information:

Weekends and holidays fill quickly so plan ahead and book today.

  • Contact: Email: capt.gaelyn@sailbluehawaii.com
  • Phone: (808) 347-0235 ​
  • Location: Kewalo Basin Harbor, Slip C30, 1025 Ala Moana Blvd, Honolulu, HI 96814​

For more details and to view available tours and sailing adventures, visit our ocean activities page:  https://www.sailbluehawaii.com/hawaii-ocean-activities/

If you need assistance with booking or have specific questions, do ask!

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easy sunset cruising

Start Keiki Young on Hawaii Private Sailing Charters

A potential client the other day asked about the child age limit for a Hawaii private sailing charter. When I said “there is no limit” he signed up immediately for a day-sail, 6 family members on board. The keiki had a blast and, with life jackets on, with an adult, the little ones gleefully sat on Kaikiwi’s forward deck. “The best seat in the house”, I call it. Sometimes you get wet, which often pumps the kids to laugh even more.

The Foredeck is not just for Keiki

Hawaii private sailing charters cover every type of request: proposal, saying “I Do”, sunrise cruise, adventure day-sail, (romantic) sunset cruise, sailing lessons, life celebrations and ash scattering. 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. Create your own adventure, any day, any time of day.

Keiki having a thumbs up moment…one of many

Hawaii Sailing at it’s Best: with the Whole Family

The easiest way to proceed is to email Sail Blue Hawaii (captain probably has hands on the wheel and can’t chat right now). We are priced right to get you out there!    Pricing depends on number in your group, duration desired, etc, so email for your personalised quote.  Indicate the number in your party, age of young ones, what kind of charter you want and when you are traveling. 

Dreams Come True in BLUE Hawaii:

This private sailing family experience may well be the highlight of your Hawaii vacation. You’ll love watching your kids respond to the sailing and the ocean; especially if they see wild life. A highlight for sure! Book now for your Hawaii private sailing charter.

On a more personal note:

Brian G, if you are reading this , please reach out. In 2016, your lovely little one became my first mate. Gosh, she is a young lady already.

capt.gaelyn@sailbluehawaii.com

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://www.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

Let’s Go Hawaii Sailing

When you get to your hotel room, even before!, and settle in, the first thing you do, I guarantee, is look out at our azure blue pacific ocean. It just pulls you in.  Then the idea occurs: let’s go for a private sailing charter; let’s go Hawaii sailing. Wave the Waikiki tour bus goodbye. Book Sail Blue Hawaii for your day-sail adventure. You will not be disappointed.

Highlight of our Hawaii vacation

I’ve heard that a lot. I heard it again this week:

Thank you, Capt. Gaelyn.  It was indeed a great experience for all of us.   Certainly, the highlight of our trip to Oahu…..- guests from LA and Germany

Such a simple statement but it means the world to me. All the hard work to keep the boat sparkling clean: the wax waxed, the stainless stainless, the rig safe, the sails solid, the hull clean; on it goes. Few people know what to takes to make a boat the “best-kept charter boat in the islands.” All that hard work and all it takes is that simple statement to know it is all worth it. Your joy becomes my joy.

Kaikiwi is upper right..sailing south (to Tahiti, we wish LOL)

The Best Day-Sail !

The photo’s story: My LA client was going to hike Diamond Head after his charter. I said “look for me”. He did… and… he found me. From the top of Diamond Head with his best lens: there is Kaikiwi, full sail. In the original photo, the zoom-in capacity is brilliant. The hazey grey in the photo is the vog coming from the Big Island’s volcanic activity.

Don’t Dream Your Life, Live Your Dream

Email Sail Blue Hawaii today for your custom quote. The choice is all yours:

a sunrise cruise, an adventure day-sail, a sunset cruise, a whale sail (whale watch, if lucky), an any-type-of sailing charter!. Let’s go Hawaii sailing.