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Chatham Yacht Club

TEACHING LOVE OF SAILING ON PLEASANT BAY SINCE 1921

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Meet your Sailing School Instructors

This page will be updated as staff information and bios become available.

2026 CYC SAILING SCHOOL STAFF

Program Director: Beth Herbst

420s  
 420 Race Coach: Sophie Dart
 Helmsman Class Director:

Alex Wesp

 Helmsman Class Instructors:

Jamie Eslick - Sr Instructor

Sam Bartlett

 Optimist  

 Opti Race Team Coach &

 Opti Advanced Class Director:


Julia Scipione

 Opti Advanced Instructor: Eli Gertsberg
 Opti Intermediate Class Director:


 Opti Intermediate Instructors:

Jack Kurtowicz

Leah Parker

 Opti Beginner Class Director:
 Opti Beginner Class Instructors:

Jessica Scipione - Sr Instructor

Jack Kurtowicz

Leah Parker

 Beetle Cat  
 Crew Class Co-Directors Brooke Bartlett
  Rosie Benson
 Crew Class Instructors


 Crew Class Jr. Instructors

Chase Berner

Maret Downs

Annamarie Hubbell

Lucy Lipson

Jake Parker

Lucy Richmond

 Sunfish  
 Recreational Sailing Class Director:
 Recreational Sailing Class Instructor:

Ada Elizabeth Hubbell

Brooke Bishop

 Recreational Sailing Class Jr. Instructor:

Chase Berner

Maret Downs

Annamarie Hubbell

Lucy Lipson

Jake Parker

Lucy Richmond

 Substitute Instructors  
 Substitute Instructors:

Emery Benson

Sean Cahaly

Roque Coelho

Millie DiRocco

Ellie Downs

Jude Luciano

Lucas Proia

Lillian Stoddard

Ainsley Reydel


 Waterfront Operations Assistant Jamie Eslick


PROGRAM DIRECTOR

Beth Herbst


Our staff is the foundation of our program. This year, we have a mixture of returning and new staff. The 2026 instructors are racing enthusiasts, sportsmanlike competitors, and passionate teachers. They are a truly inspirational group for younger sailors to learn from.

Our Summer 2026 staff will build on CYC’s reputation as a yacht club valuing sportsmanship, competition, and learning. Every student has a place in our program. We hope that they will leave sailing school each day having learned something.


CREW CLASS (Beetle Cats)

Crew Class Co Lead Instructors:


BROOKE BARTLETT  Brooke Bartlett is from Wayland, Massachusetts, and spends her summers in Chatham. She has been sailing at CYC since the age of six and is a member of the 420 race team. Over the years, Brooke has achieved success at numerous regattas across Cape Cod, earning multiple podium finishes.  Brooke’s favorite part of coaching sailing is building connections with her students, spending time outdoors, and helping young sailors grow and improve their skills on the water. She loves watching her students gain confidence and develop a passion for the sport.

This summer, Brooke is especially excited to spend time with friends and enjoy everything CYC has to offer. When she’s not out on the water, you can usually find her at the hockey rink. She also holds a Level 1 Teaching Certification.

ROSIE BENSON Rosie is 16 years old and going into her junior year of high school. She goes to school at Broadneck high in Annapolis Maryland. For summer 25’ she is working as the class lead for crew class! She has sailed at CYC for 10 years and is her 3rd year teaching. She enjoys hanging out with friends and family, loves to paint, go for walks, and read when not on the water. She is super excited to be at CYC!ummer and make new memories with our sailors!

Crew Class Junior Instructors:


 OPTI CLASS (Optimist)


Opti Race Coach & Opti Advanced Instructor: 

JULIA SCIPIONE

Opti Intermediate Lead Instructor:

Opti Intermediate Instructor:


LEAH PARKER Leah is an instructor for the Opti Beginner/Intermediate classes for her fourth summer instructing. She lives in Princeton, NJ in the winter and is a rising senior at Hopewell Valley Central High School. She grew up sailing at Stage Harbor, moving to CYC last summer. This is her 5th and final year racing 420s but plans to continue racing in college. When not at CYC, you can find her playing/teaching tennis and making art. She can’t wait for another amazing summer filled with helping students fall in love with sailing and making memories!

Opti Beginner Class Director:

Opti Beginner Instructors:


LEAH PARKER Leah is an instructor for the Opti Beginner/Intermediate classes for her fourth summer instructing. She lives in Princeton, NJ in the winter and is a rising senior at Hopewell Valley Central High School. She grew up sailing at Stage Harbor, moving to CYC last summer. This is her 5th and final year racing 420s but plans to continue racing in college. When not at CYC, you can find her playing/teaching tennis and making art. She can’t wait for another amazing summer filled with helping students fall in love with sailing and making memories!


Helmsman & Race Team (420s)

420 Race Coach

SOPHIE DART

Helmsman Lead Instructors:

ALEX WESP

Helmsman Instuctor:



Recreational (Sunfish)


Recreational Sunfish Lead Instructor: 


Recreational Sunfish Instructors



Substitute Instructors

Chase Berner

Chase Berner is 14 years old and will be going to nauset high school next year. He has been sailing for 8 years but it is his first year on staff. He enjoys anything to do with the ocean and playing sports in his free time.

Maret Downs

Maret Downs is a rising freshman at the Potomac School in Virginia. This will be Maret’s sixth year sailing at CYC and her first year as part of the CYC staff. In her free time, Maret likes to spend time with friends and family. She also enjoys playing softball and tennis.


Annamarie Hubbell

Annamarie is 14 years old and is a freshman and Acton-Boxborough Regional High School. She a substitute instructor and is also in her second year of Helmsmen. When not on the water, you can find her on the lacrosse field, playing field hockey, and playing basketball.


Lucy Lipson

Lucy Lipson is going into 9th grade at The Potomac School. She is excited to be a Substitute Instructor this summer. When not sailing, she likes to play lacrosse.

Jake Parker

Jake Parker is a sub instructor at CYC this summer. This is his first year on the CYC staff and he has been sailing since he was 7. His going to be a Freshman in high school at Hopewell Valley Central High School. When he isn’t on the water, he likes to play soccer, golf in the summer, and ski in the winter.


Lucy Richmond

Lucy Richmond is 14 and going into her Freshman year at Acton-Boxborough High School in Acton, Massachusetts. This year she is working at CYC as a substitute instructor. Lucy loves the beach and spending time with friends and family. When she is not sailing she spends lots of time training and dancing ballet!

Zach Wesp

Zach is 14, this summer will be his 8th summer sailing and his first year working. Zach goes to the Cape Cod Lighthouse Charter School and in the fall he will be going into 8th grade. When off the water, Zach enjoys playing lacrosse and spending time with family.


Chatham Yacht Club | P.O. Box 531 | North Chatham, MA 02650

CYC is a 501(c)(3) Non-Profit Organization. Your donations are tax deductible!

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