Executive Director


Amy Tripp is a physical education teacher at Gilford High School, as well as a certified lifeguard instructor, personal trainer and volleyball coach. Her teaching, coaching, administrative and extensive work with young people allow her the expertise to oversee the sailing program in the position of executive director. She enjoys hiking, traveling and spending time with her family.

Head Instructor

Seth Wilkinson, from Sanbornton, New Hampshire, was a camper, junior instructor, instructor, and now is the head instructor at LWSA. He is currently studying chemical engineering at Clarkson University. In his free time he enjoys racing J80s on lake Winnipesaukee as well as skiing and playing lacrosse.


Samih Shafique is a Gilford local who has been with the LWSA since his days as an 8 year old camper. Since then, he’s been a junior instructor and instructor for the youth camp before moving on to handle our adult sailing programs. He is a graduate of Gilford High School and Boston University and an incoming graduate student at the Boston University School of Medicine.

Parker Caswell has been an avid sailor starting classes at age 6,  in Maine. He has experience teaching children and adults first on Peaks island in Maine and most recently at the Squam lakes Association. This is his third year as an instructor. In his spare time he enjoys working on his boats, racing sail boats and spending time with friends.

Clare Shanahan has been at the LWSA since she was ten years old and is in her third season as an instructor. In addition to sailing, she plays field hockey and ski races in the off season. She now attends New York University where she is studying journalism and environmental science.

Gavin Divelbiss has been with LWSA since 2011 as a camper, Junior Instructor , and instructor.  He grew up sailing on Newfound Lake and Massabesic Lake and is a passionate racer.  He attends Massachusetts Maritime Academy where he studies Marine Transportation and competes on the sailing team. In his free time he enjoys being on the water, mountain biking, and traveling the world. 


Ian McCabe has been with the sailing camp since age seven and over the years has been a Junior Instructor and Instructor. Ian spent his childhood summers on Lake Winnipesaukee with his family and recently moved here full time. He is passionate about law and government studies and has interned with the New Hampshire State Senate and looks to pursue this passion further in college. Some of his favorite hobbies include baseball, soccer, skiing, and jet skiing around the lake. 

Junior instructors

Oren Avrahami


Luke Cassidy

Jessie Trimper

Anna LaDue


Toby Wilkinson, from Sanbornton, New Hampshire, has been at LWSA as a camper, Junior Instructor, and Instructor since 2013. He currently attends high school at Proctor Academy in Andover, New Hampshire, where he is a member of the alpine skiing, road biking, and mountain biking teams. When not sailing or in school he enjoys hiking and reading.


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