Honolulu TRADEWIND sailing, where any time is a good time to be on the water. Highlight your Hawaii vacation aboard a sailboat on our beautiful cobalt blue Pacific Ocean. Here is our recommendation on SOME OF the MANY 5 best Honolulu private sailing charter ideas.
Private Sailing ideas; Waikiki, Hawaii
- A tradewind day-sail. 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 tradewinds so any time of day is a good time to go sailing…sunrise, morning, afternoon, or sunset. IT’S ALL GOOD!
- A sail to take in the beautiful views of Oahu and beyond. Outstanding 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.
- A private day-sail to capture sightings of marine life. “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. (I believe we did see a mermaid one time; sh sh sh……………)
- Birthday celebrations at sea. What better way to celebrate that special day for that special someone than aboard a private yacht charter in Honolulu?
- Corporate Events. Celebrate with the team onboard a sailing yacht off the Honolulu coast. How better to raise morale and reward them for a job well done?
Many many ideas for your custom cruise are accepted and sailed
https://youtube.com/shorts/PBDlY4_DZnA
This was one beautiful day to sail around Diamond Head into Maunalua Bay. My guests got the last good sailing in before Oahu was rocked by a decent winter storm. Not all Sou’Westers are bad 😎. We were lucky. What a peaceful time.
View other movies on Sail Blue Hawaii’s youtube channel
When should we book?
NOW!! Booking ahead of time is a good idea just to secure your sail. Today is also a perfect day for a HONOLULU PRIVATE SAILING CHARTER; last-minute requests can sometimes be accommodated but don’t count on it; and, ANY occasion is a good one to get out on the water with Sail BLUE Hawaii.

a rare view while on a HI day-sail:
Koko Crater
Email with your idea for your Honolulu Private Sailing Charter sail. Your experience aboard may well be the highlight of your HI vacation
Locals too! Take a day off and let’s go sailing capt.gaelyn@sailbluehawaii.com
The Horizon is NO Limit
