​​​(808) 382-4437​

Sailing and Learning the ALOHA Way!

Best Sailing School of Honolulu Award 2023!
Best Sailing School of Honolulu Award 2022!
Best Sailing School of Honolulu Award 2021!
Best Sailing School of Honolulu Award 2020!
Best Sailing School of Honolulu Award 2019!
American Sailing Association's Outstanding Instructor of 2013!

Welcome to Waikiki Sailing School.  Whether you are joining us for a sailing charter or sailing lessons, Waikiki Sailing School is affordable and fun for the whole family.  Join us for an afternoon sail off Diamond Head or a multi-day, over-night cruise.

Throughout our website you will find an abundance of helpful information.  We offer custom packages for every budget and experience level.  More information about our lessons, charters, and pricing can be found on the Courses and Charters & Ratespages of our website. 


Sailing dates for ASA Courses (lessons) and charters are selected by you, the Student(s) and/or Charterer, tailored to fit your schedule. Sailing dates are confirmed when Waikiki Sailing School receives your deposit and registration form.

​All of our Captains are United States Coast Guard (USCG) certified with decades of sailing experience. Let us help you find your sea legs for the first time or chart your own course across the Hawaiian Islands.

All of our sailing courses are endorsed by the world’s leading authority on sailing instruction — The American Sailing Association (ASA).