Waikiki’s BEST Boat Tour

It’s hot. Its summer. How best to escape the heat than to get on your own private yacht and enjoy Waikiki’s BEST boat tour. Private sailing (you are not sharing the boat with another group) on “Kaikiwi”, the 42 ft Beneteau 411 featured here on my website, has lots of shade so time of day does not affect heat/ sun exposure. It also has lots of space for “bow babes” to soak up the sun and get that rich Hawaiian sun tan. “Kaikiwi” is your yacht for however long you want to sail.

Enjoy a cooling Hawaii trade wind sail.

Feel the fresh trade wind cooling you off immediately as we set sail (YES, we actually DO sail) from Kewalo Basin, 2 miles west of Waikiki. 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 balmy year-round trade winds, so, any time is a good time to go sailing…..✨✨enjoy a magical SUNRISE cruise, a full sail morning and afternoon adventure sail, or a romantic/ peaceful SUNSET cruise.✨✨.  It is all good. 

Sail BLUE Hawaii does not have a liquor license, so please do bring your beverage of choice to help keep you hydrated and COOL (water is supplied). There is ice and a cooler on board for your convenience.

Why choose a sailing charter?

Any occasion is a great one to get out sailing on Hawaiian waters, to enjoy some relaxing and refreshing ocean time, privately and with loved ones. You are NOT sailing with “49 of your closest friends”. 30-60 pax boats, sailing masses of strangers together, seem to have taken over our waters. Sail BLUE Hawaii offers an intimate and exciting atmosphere where you can lay back and catch up with friends and family. Or just spend some quiet and reflective time on your own at the bow. Yes, this is custom sailing…your choice of gentle or adventurous…your captain LISTENS to your specific request.

Whether you are a seasoned sailor or have never been on a sail boat before, the “oh yes” you feel ( or murmur or SHOUT!) when the sails are set and that engine is turned off is real. I hear the sighs of peace/ relief every time…sailor and newbie alike. No engine, much peace. So, say goodbye to the noisy, smelly motorised boat tours that speed through the waves giving you whiplash (and others boat wake :-() ) and are so annoyingly noisy..so much so you can’t even sit back and relax and chat.

Sign up for Sail BLUE Hawaii’s custom private charter, Waikiki’s best boat tour, the one with NO engine noise and smells because, yes, we actually SAIL.

custom sailing…your choice of gentle or adventurous…your captain LISTENS to your specific request.

Hawaii’s BEST July 4th Boat Charter

Enjoy Hawaii’s BEST July 4th boat charter…whether you are local (or, ESPecially if you are local !!) or tourist, you will not regret sailing with Sail BLUE Hawaii. The experience may well be the highlight of your HI vacation or the end of your work week.

Where do we go?

“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.

Because this is custom sailing, we can sail any time of day you want and whatever length of time you wish. 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. 

July 4th Fireworks

The Waikiki fireworks show that were especially dynamic, are still not happening after a long break since the pandemic. If you wish to see fireworks from your private yacht, they will appear from far away; after the 8pm Hilton show. Worth staying out late for? Maybe. Either way, choose your time of day and enjoy your day off by laying back on your private sailing charter. Choose Sail BLUE Hawaii, Hawaii’s BEST custom July 4th private boat charter.

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://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

5 best private sailing charter ideas

  1. Celebrate Dad!. On Sunday, I had the delight of taking a family of six out on an eight-hour privater sailing charter. “Eight hours?’ you say “way too long”. Yes for many, but not this family. The day dawned glorious and with flat seas and light wind we throw off the bowlines and sailed south without a care in the world. As the private sailing charter progressed, the winds increased but stayed moderate even outside the notorious Diamond Head windline. What a spectacular day. “This was my best Father’s Day yet. Mahalo for making it so special”. My pleasure!

2. Celebrate LOVE. Last week, at sunset, John brought his girlfriend aboard Kaikiwi for their very own private sailing charter. It was a surprise for her but that wasn’t the only surprise she was getting that evening. There was a ring involved. Just before sunset, he got down on his knee ( a hard thing to do on a moving sail boat) and proposed. She said “YES!!” You too can make your proposal the highlight of your lifetime by choosing a private sunset cruise. Sailing is the most romantic type of boating.

Check out my Tube channel for an idea of how to propose aboard your private sailing charter:

https://www.youtube.com/watch?v=x9LO9YerNDg

A birthday surprise sailing charter will be remembered forever

3. Celebrate a birthday. Carmen called me to book a private sailing charter as a surprise for her husband’s birthday and what a surprise it was. He had tears in his eyes as he boarded Kaikiwi. He had always wanted to sail, had watched videos and talked about it as a dream but never thought he could have it. Carmen made it happen and they will be back for more sailing.

4. Celebrate your Hawaii vacation. Perhaps you have never sailed before and the thought of it is hugely outside your comfort zone. An easy boat tour may be all you want and I can certainly accommodate that. Whether or not we raise sail, we can do an easy boat tour up the coast to check out the island of Oahu from a different angle and her marine life! Just explain your booking needs when you call and you will be completely taken care of.

5. Celebrate life. If you are a serious sailor, a full sail private sailing charter is for you! Yes, this is where we go full out, heel over and let the wind take Kaikiwi to her finest sailing ability. She is a perfect sailing machine for Hawaii waters.

Give Sail Blue Hawaii a call for all your boating needs and you will have your own private sailing charter customized just for you.

Full sail or boat tour? Your choice!