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)

Hawaii Tradewind Sailing at its Best

Welcome aboard Sail Blue Hawaii to experience Hawaii tradewind sailing at its best. Leave the tour bus behind and experience something different and unique…it may well be the highlight of your Hawaii vacation.

Where do we sail to?

“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. This is not “destination” sailing.  “Destination” is sailing.

What if I have never been on a sail boat before?

The beauty of a private sailing charter is that the experience your little group has is customised (Kaikiwi is USCG certified for 1-6 passengers). You don’t need to have ever sailed before: I can tone it down or ramp it up to meet your group’s needs and expectations. Sailing outside Diamond Head is not for everyone. So, if your group decides so, we don’t go. It’s easy enough; just tell me who you all are… newby or a seasoned sailor, or part and part.

Email capt.gaelyn@sailbluehawaii.com today to book your Hawaii tradewind sail. The beauty and quiet of your private sailing charter may well amaze you.

View other movies on Sail Blue Hawaii’s YouTube channel !

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’s BEST Tradewind Sailing

Sai! Blue Hawaii offers a full range of sailing options; from casual sightseeing boat tours to special occasions (weddings, proposals at sea) to Hawaii’s BEST tradewind sailing. Whether you have never stepped foot on a sailboat before (exciting first time !!) or you are an old salt, your private sailing charter is catered to you. (Visit the “Let’s go Sailing” page for ideas.)

Where do we sail to?

“Kaikiwi” sails from Oahu’s (protected) south shore, near 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. We do look for mermaids too. The first to see one gets a free boat ride. 🙂
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.

Whoever needs to arrive to be happy?

Where in the world are you going to get this kind of tradewind sailing? Only here in Hawaii ! Sai! Blue Hawaii offers Hawaii’s BEST tradewind sailing daily on your vey own private sailing charter. Other companies may pop a little sail out but mostly motor-sail. Sai! Blue Hawaii offers REAL sailing. Who needs a theme park when you can do this for real? Remember, gentle sailing is offered too! The range is limitless. Just voice your pick.

DON’T DREAM YOUR LIFE: LIVE YOUR DREAM

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.