​​​(808) 382-4437​

Aloha and E Komo Mai (welcome!)   Since childhood, I have loved the sea with a passion for sharing it with others.  With decades of sailing adventures throughout the Pacific, my goal is to provide you with the best sailing experience of your life.

Our Hawaiian waters and climate are ideal for sailing in comfort all year. The unsurpassed beauty and incredible marine life is truly paradise. 

Mahalo for visiting my website.  Captain Matt

About Us

Waikiki Sailing School is a certified American Sailing Association (ASA) School located in Honolulu, Hawaii. At WSS we pride ourselves on going the extra mile for our clients, whether you are taking the helm for the first time or have earned the title of “Old Salt” amongst your friends, we are here to indulge your craving for the wind and sea. 

At WSS, we welcome all sailing experience levels as well as those that just want to get out on the water for a little R&R. Unlike other sailing schools, all of our courses are taught in the big blue ocean. We also offer a variety of Cruise & Learn packages that will not only give you a solid footing on the sailboat of your choice, but we also give you THE experience of a lifetime.

WSS will show you hidden anchorages, gorgeous seascapes and provide unparalleled customer service. We won’t waste your time with a non-descript boat or tour packed full of people. At WSS we give you an intimate, one-on-one approach to sailing.

So if you’re looking for a Captain with decades of sailing experience in Hawaii and the South Pacific, small class sizes, fun, and affordability in the waters off Hawaii, consider getting your feet wet with Waikiki Sailing School today.