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Staff and Fleet

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Meet Our Passionate Team and Explore Our Impressive Fleet

At Diamond Lake Sailing School, we pride ourselves on our team of dedicated staff and our versatile fleet of sailboats. Each member of our team brings unique skills and experiences, contributing to a rich learning environment for our students.

All of our instructors are First Aide, AED, and CPR Certified through:


Our Sailing Instruction Team

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Timothy Hesse
Sailing Director

Background: With the Chicago Yacht Club as his home club, Timothy is an accomplished sailor. He's in his fifth year as an instructor and is also a graduate of the DLYC sailing program.


CHICAGO YACHT CLUB: Jr. Member (March 2020 - Present)

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UNIVERSITY OF NOTRE DAME: Club Sailing Team (August 2023-Present)

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LATIN SCHOOL OF CHICAGO: Sailing Team (Fall 2019 - Spring 2023)

  • Captain, Senior Year

  • Coaches Award, Senior Year

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US SAILING : Level One Certified since May 2022 


DLYC: Sailing Instructor since 2019 

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Mason Coles
Sailing Instructor

Since 2020

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Kiera Hogarth 
Sailing Instructor

Since 2023

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Lindsay Gowler
Sailing Instructor

Since 2022

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Kirsten Usher 
Sailing Instructor

Since 2023

Our Fleet

​The Diamond Lake Sailing School fleet is tailored to accommodate sailors of various skill levels. Our fleet includes:

  • Optimist Sailboats (Opti's): The cornerstone of our beginner training, perfect for young sailors learning the ropes.

  • Sunfish Sailboats: Ideal for single-handed sailing, offering a step up for those progressing from Opti's.

  • 420 Sailboats: These double-crewed boats provide advanced sailors with the opportunity to refine their skills and teamwork.

  • Butterfly Sailboat: A unique addition to our fleet, offering a different sailing experience.

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