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Jr. Sailing Instructors

Katie O'Keeffe

Program Director

We don’t send our kids to sailing class to win trophies. We do it because doing things that are hard are worth doing. We do it because our children should understand the overwhelming power of wind and water and how to harness them. We teach seamanship to impress on them the value of meticulous care, preparation, and technical skill, things that will lead to success in a world of constant and unexpected challenges. And most importantly, sailing is really fun!

Sophia Peck

Sr. Instructor / Race Coach

Hi, my name is Sophia Peck and I'm so excited to be back for my second summer! I grew up sailing on Cape Cod from when I was 9 at West Dennis Yacht Club and Wianno Yacht Club. I sailed both Optis and Club 420s, as well as FJs/420s at Tabor Academy where I was the captain for the 2021-2022 season. I just finished my first year on the Cornell Sailing Team and am so excited to get back out on the water at Hyannis Port!

Ty Cronin

Sr. Instructor

Hi, my name is Ty Cronin I have 11 years of sailing experience including sailing Optis, 420s, Cotuit Skiffs and Wianno Seniors at the Cotuit Mosquito Yacht Club. I have raced 420s for my high school varsity team for 3 years and am looking forward to continuing to sail at Fairfield University this fall. I am Level 1 Sailing Instructor certified which includes completion of a Safe Boating course, holding a valid SafeSport certificate and current and up to date First Aid and CPR.

Zach Kennedy-Bailey

Jr. Instructor

Hi everybody, my name is Zach Kennedy-Bailey. I've been sailing my whole life here in Hyannis Port. I went to sailing class here for 5 years, which I loved. This is my first year here as an instructor this year. I can't wait to help teach with all of you this summer and have fun doing it.

Luke Millowitz

Sr. Instructor

Hi everyone, I’m Luke Millowitz and I am so excited to get out on the water with you all! This is my 2nd year instructing at HPYC but I have grown up sailing here since I was 7. I have racing experience across many boats such as fevas, 420s, Wianno Seniors and more. I am CPR and Wilderness first aid certified. Next year, I will be playing football at Denison University. Can’t wait for great experiences on the water!

Halle Dempsey

Assistant Instructor

Hi! My name is Halle Dempsey and I am so excited to be back at HPYC this summer as an instructor. I am 17 years old and will be a Senior at Needham High school this upcoming year!! I am currently racing with the Needham sailing team and I enjoyed racing on the ski team this winter. I also enjoy playing tennis and golf during the summer. I joined the HPYC program at 7 and have loved to sail all different kinds of boats such as beetlecats, typhoons, sunfish, 420s, and optis.

Tiernan O'Kane

Sr. Instructor

Hi all, my name is Tiernan O'Kane and I've been sailing since the age of 8. I started out sailing for fun in Sunfish. In 8th grade, I transitioned to sailing 420s and did so for the rest of high school. I am currently sailing in college on the team at UMass Amherst. I love sailing for the moment when the boat is trimmed perfectly, flying on the surface of the water and you feel on top of the world. I am excited to return to HPYC this summer to share my sailing experience!

Maren Finan

Assistant Instructor

Hi everyone! My name is Maren Finan, and I have been sailing at HPYC since I was 7 years old. I have experience sailing Beetlecats, Optis, 420s, and Sunfish. This is my second year teaching, and I am so excited to get back on the water! I am an incoming junior in high school and I am Red Cross certified for Babysitting and Child Care. I look forward to seeing our returning sailors and meeting new ones this summer, for a great season of learning, racing, and having fun!

Nathalie Gregg

Jr. Instructor

My love for sailing began when I was first introduced to an opti when I was 4 years old. I really enjoy sailing and racing in regattas because it has allowed me to gain a sense of independence on the water which has helped me work on my confidence and being calm under pressure. It has developed my leadership skills, but it has also enabled me to widen my love for water sports. I also started kiteboarding, which has added another dimension to my knowledge of the wind and water!

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