Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921

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Meet your 2020 Sailing School Instructors!


Jeff grew up at the club sailing Beetles, Sunfish, 420s, and Daysailors. Since 1998, he has been an English teacher and coach on Cape Cod at Dennis-Yarmouth Regional High School. Additionally, he has run youth programs in human rights, basketball and tennis while also serving on the board of directors for Homeless not Hopeless, which helps people transition out of homelessness into sustained work and housing. 


Connor Blanchet

Connor is the head 420 coach at CYC. He has been at this club for well over a decade now and its has a special place in his heart. Connor has  been living in the Canadian wilderness for the few months before this sailing season began, planting trees and staying away from Covid. He  can't wait to have a blast this summer at CYC despite the challenges that we will face in this time. But from his experience, Connor is  fairly certain that nothing can kill our Chatham spirit!

Abby Lenox : Helmsman & Race Team Instructor

Wendy Taylor : Recreational & Crew Instructor

Wendy hasn't spent a full summer at CYC since 2013, but she's excited to be back where her love of sailing began! She is a rising Senior at Middlebury College, where she is double majoring in Elementary Education and English. Wendy hopes to share and hone her love of teaching this summer in preparation for a career in the classroom. Outside of sailing, Wendy loves choral singing, doing puzzles, and making art with her friends.

Caitlin Fitzmaurice : Junior Recreational Instructor

Caitlin has sailed at CYC since she was seven years old and in Beetle Cats. Since then, Caitlin has raced Optis and 420s. Also, in the past couple of summers, she has been a crew class instructor at CYC and an instructor at PBCB across the bay. When  not sailing, she likes to ski, row crew, and listen to music. Caitlin loves racing and teaching sailing and is so excited for another summer on the water!

Hank Bailey - Helmsman Instructor

Hank has been sailing on CYC since he was 10. This is his second year teaching and will be assisting Connor as helmsman instructor. When Hank is not sailing he enjoys going to the beach, playing tennis and being with friends. Hank will be a freshman in the fall at Roger Williams University.

Will Bailey - Helmsman Instructor

Will started sailing at Chatham Yacht Club when he was 7 years old. He is currently on the 420 race team, his school team, and plans to sail in college. Will has been a substitute instructor before in addition to crew class instructor. Will also enjoys playing on his high school soccer team.


Ashley Dart

Ashley has been sailing at CYC since she was 6 years old.  She is excited to be running the Crew Class program this summer and thrilled to be coaching the race team with Connor.  Growing up, Ashley sailed competitively in Opti, Laser and Club and i420 fleets.  Ashley hopes to spread her love for sailing and the environment within the CYC community.  Ashley, a rising senior at NYU, is studying documentary film and photography.  Outside of sailing, Ashley enjoys traveling, skiing, the outdoors and being creative. 

Schuyler Bartlett : Crew Instructor

Schuyler started sailing at Chatham Yacht Club when she was 6. She loves sailing, and has loved every minute of every year at CYC. She is a member of the race team along with being a junior instructor. She is a rising junior at The Rivers School in Westin, and when not working or sailing she enjoys playing field hockey, performing in musicals, and laughing with her friends, family, and dog, Lucky.

Karina Lamoreux : Crew Instructor

Karina will be a junior next year at the Bay School of San Francisco. She has been sailing at CYC since 2010 and has enjoyed being able to make strong friendships through the CYC program. Karina likes playing tennis and lacrosse and spending time with friends and family. She is excited to teach crew class this year!

Izzy Maggioni: Opti Race and Opti Advanced Instructor

Izzy has been sailing on Pleasant Bay for 13 years and teaching at CYC & PBCB for 6 years.  She is super excited to be teaching the Advanced Opti Class, as well as, coaching the 420 Race Team.  When she's not sailing, Izzy enjoys running and hanging out with friends.  Izzy is a rising sophomore at Trinity College where she plans to major in biology.

Sophie Maggioni : Opti Advanced Instructor

Sophie is a rising senior at Wellesley High School, and a captain of her high school cross country and nordic skiing teams.  She's been sailing the bay for 11 years, including 4 years working as an instructor. This summer she's excited to be working as an instructor for the Opti Intermediate and Crew B classes, as well as teaching at PBCB across the bay.  She's looking forward to hanging out at the beach, spending time with family and friends, and working on her sailing and boating skills this summer!

Calder Robbins : Opti Race & Intermediate Instructor

Calder learned how to sail at the age of 6 with Cape Cod Sea Camps. He joined the Chatham Yacht Club school seven years ago and has been an active member sailing beetle cats, 420s, and lasers. Calder has taught the last two years as a junior instructor for the Beetles and instructor for Sunfish. This year he is excited to work with both the advanced opti sailors and the laser class. When not sailing, Calder enjoys fishing, photography, and fencing.

Grace Gunsalus : Opti Beginner Instructor

Grace started sailing at CYC when she was 9 years old and worked her way through sailing school. She will be a rising freshman at Fairfield University and will join their club sailing team. When she is not on the water, Grace enjoys hanging out with her friends and spending time with her family. She’s so excited to be back coaching on the bay this summer!

Substitute Junior Instructors:

Chad Bartlett

Chad started sailing at Chatham yacht club when he was seven years old. He loves to sail and race and will be on the 420 race team this summer. When not sailing Chad enjoys playing lacrosse and spending time with family and friends.

Colin Boland

Coco Fitzmaurice

Coco has sailed with CYC since she was 6 years old, racing in Beetlecats, Optis, Sunfish, and 420s. She is excited to be a substitute instructor out on Pleasant Bay in addition to being in Racing Skippers. Outside of sailing, she rows for her school, plays music, and spends time with her friends.

Amelia Gassner

Amelia started sailing at a very young age in beetle cats when she was 6. She is very excited to race 420s in pleasant bay and around the cape. Amelia enjoys rowing and cooking when not sailing.

Sarah Lenox

Sarah Lenox started sailing in Beetle Cats at CYC when she was 7.  She enjoys sailing on Pleasant Bay with her family and friends.  In her free time, she enjoys playing soccer and hanging out with friends.  Sarah is excited to be joining he 420 race team this year.

Zoe Maggioni

Zoe has been sailing at CYC for 8 years.  This year she is working as a substitute instructor and she is also sailing as a part of the 420 race team.  When she's not sailing, she enjoys running cross country and hanging out with her friends and family.  This year she will be a sophomore at Wellesley High School.

Jack Szymanski 

Jack began in Beetle Cats at CYC when he turned 7. He now loves to race 420s around the Cape and teach Beetle Cat classes during the summer, and this is his third year as part of the CYC staff. Jack also enjoys playing classical piano and tennis.

Julia Szymanski

Julia started sailing in beetlcats at 7 years old. She loves sailing in Cape Cod with family and friends. She is excited to be joining the 420 race team this summer. Next year, she will be a high school freshman at Oak Knoll School in Summit, New Jersey.

2020 CYC Sailing School Staff:

Program Director:
Assistant Program Director:
Jeff Howell
Connor Blanchet
Ashley Dart
420 Race Coaches: 

Connor Blanchet

Ashley Dart

Opti Race Coaches: 

Izzy Maggioni

Calder Robbins

Crew Director: Ashley Dart
Recreational Instructor:

Wendy Taylor

Opti Advanced:

Izzy Maggioni

Sophie Maggioni

Opti Intermediate:  

Opti Beginner:

Calder Robbins

Grace Gunsalus

Helmsman: Abby Lenox



Schuyler Bartlett

Wendy Taylor

Karina Lamoreux

Race Team: 

Abby Lenox


Hank Bailey

Will Bailey


Junior Instructors - Crew:

Junior Instructors - Opti:

Cody Lamoreux

Tucker Lamoreux

Cailyn Murphy

Junior Instructor - Recreational:

Caitlyn Fitzmaurice

Junior Instructors:

Chad Bartlett

Colin Boland

Coco Fitzmaurice

Amelia Gassner

Sarah Lenox

Zoe Maggioni

Jack Szymanski

Julia Szymanski

Junior Opti Instructors

Cody Lamoreux - Junior Opti Instructor

Cody lives in San Francisco but has spent his summers sailing at CYC since he was very young. He loves to race and is a part of the 420 race team. During the school year, Cody races on his high school’s varsity sailing team in FJ’s. When he is not sailing, Cody enjoys playing sports and spending time with his friends.

Tucker Lamoreux - Junior Opti Instructor

Tucker has been sailing at the Chatham Yacht Club for as long as he can remember. He lives in San Francisco, CA, and will be a sophomore at the Urban School of San Francisco in the fall. This summer, Tucker is a Junior Opti Instructor and will be on the 420 race team. When Tucker isn't sailing, he enjoys playing soccer and spending time with his friends

Cailyn Murphy - Junior Opti Instructor

Cailyn started sailing on Pleasant Bay at a very young age. She joined the Chatham Yacht Club program at age 7. She is excited to be joining the 420 Race Team this summer. When she is not sailing, you will find her in the hockey rink or hanging with her friends.

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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