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:

5 BEST reasons to choose a Private Hawaii Sunset Cruise

Honolulu sunset sailing: a beautiful time of day to be on the water. What can be more romantic than sunset aboard a sailboat on the Pacific Ocean. You will want to experience a sunset cruise during your vacation in Waikiki. Here are the 5 best Hawaii sunset cruise ideas:

Honolulu’s Best Sunset Cruise

  1. Have you ever seen the green flash? On your private sunset sail, this may well be what captures your joy the most. There are theories about what makes the green flash. Check them out online. I have seen more than my share of this delicious phenomenon on numerous sunset sails.
  2. The other evening, my charterer pulled off an especially perfect surprise sunset cruise for his girlfriend. She had no idea she was about to go sailing until she got to the dock. She had always expressed a desire to be on a private sail boat/ a private boat tour. It was with teary eyes she climbed on board.
  3. Of course, saying “I do” is particularly romantic at sunset: a private yacht, just the two of you and the captain. YES, this is the perfect reason to choose a sunset cruise. Sail on a Friday evening and enjoy a fireworks display just for you! A combined sunset and fireworks cruise is a highlight…how can she say anything but “yes”in this most romantic ambiance.
  4. A life celebration/ ash scattering is particularly special in the easy sunset hours. Your sunset sail with family and friends will stay in your mind forever as you remember and celebrate your loved one.
  5. Of course, you need no reason at all to choose a Hawaii sunset cruise. It is the best time of a day. Sail out there and enjoy all that Hawaii’s beauty has to offer.

Call Sail Blue Hawaii today and sign up for your own private sunset cruise. If you are especially lucky, in the winter months, your private sunset cruise may well turn into whale watching! This Hawaii Sunset Cruise could well be the highlight of ANY vacation.

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.

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.