​​​(808) 382-4437​

​"My husband and I wanted to learn how to sail and Captain Matt was there to help us every step of the way. We feel so fortunate to have had this experience and we would definitely recommend Waikiki Sailing School to our friends."
--- Tina and Jim Wolcott, Scottsdale Arizona.

"We completed 3 ASA courses with Captain Matt, aboard his 33' Ranger sailboat, while sailing from Waikiki to Maui and back.  We were looking to extend our sailing experience, hence our choice to face the big waves and winds between the Hawaiian islands.
Matt enabled us to gain confidence through teaching us how to plan for, and adjust, sail trim in heavy weather conditions.  His lifelong experience as a sailor in these conditions, and his solid common sense, gave us the confidence to embark on this adventure. 
Aside from Matt's experience, we also enjoyed his calm approach to teaching, and enjoyed hearing about his lifetime of sailing and racing adventures.   Catching fish under sail was an added thrill. 
Matt's Ranger is very seaworthy and capable of some impressive speeds.    
The inter-island sailing course is ideal for gaining experience in planning, navigation, sail trim and avoiding hazards (reefs and big surf!) .  We highly recommend Matt as the person to guide you through this experience."                       --- Kim Courtenay, Canada

"Waikiki Sailing School has, by far the most experienced Captain who is an excellent teacher. The boat that we sailed on was comfortable, and impeccably maintained and clean. Our provisions were well planned. Great Captain + very nice sailboat = awesome experience! Thank you!!!"
--- L. Freed, Honolulu, HI

​"If you’re looking for a fun, laid-back way to spend your vacation look no further than Waikiki Sailing School. We loved their bare boat package! Mahalo Nui Loa, Captain Matt."
--- Melissa, Jim and Keoni, Kihei, Maui.

"Thank you for bringing my dream to a beautiful reality!  Your sailing knowledge and skillfulness is very apparent by the incredible experience you have given me.  You are a kind gentleman with such a passion and respect for the ocean.  I have nothing but great things to say to my family and friends about my experience.  I look forward to sailing with you again."    
--- Many Thanks!   S. Chester     Bremerton, WA

"Waikiki Sailing School was the best time my girlfriend and I have had in a while. The wind and salt spray off Diamond Head were thrilling for both of us and made us want to get out on the water again as soon as possible."
--- Nick and Jane Thompson, Escondido, California

Client Reviews

"I did a 7-day cruise with Waikiki Sailing School with my girlfriend and another close friend to Maui and then back along the north shore of Molokai, completing our ASA 101, 103, and 104 certifications in the process. We sailed on the Nordic 44'. Matt is a great instructor, with 50 years of experience on all kinds of sailboats. If you're serious about learning to sail, Waikiki Sailing School is the place to go."   --- Christian Monaghan, Maui, HI

"During the week. I had 3 extremely positive sailing journeys with Captain Matt. En each occasion I could learn so many topics related to all aspects of sailing. Captain Matt is very professional and he knows very well how to transmit his knowledge. I asked him so many questions and he always explained things to me with great detail and patience. The circumstances of this experience together with the wonderful setting which is to sail along Waikiki shores have made me decide to come back in April to continue learning under his tutelage! And I have a long trip from Argentina to be here!"  Richardo

"I want to thank you for taking my mother and I sailing.  My Mother, who is 84 years old loves the ocean, but was apprehensive about sailing.  You quickly made her feel comfortable and secure with your sailing expertise.  Our sail with you was beyond our expectations!  It was absolutely wonderful and we enjoyed every moment.  We will recommend everyone we know to you for a perfect sail." 
--- Mahalo,  J. Fautt    Aiea, HI

"We had a really great time training with you. I learned a great deal and feel much more confident in my ability to know what to do when. You were really great at putting skills into useful language and very patient, calm, and responsive. I still need lots of practice, but things are coming together. Thanks for your patience, great instruction, and ability to appreciate that Pat and I are at different places with our abilities and comfort levels.  Best wishes to you out there in Aloha land." 
--- Stacy and Pat McLain