Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921

Registration for 2021 Sailing School NOW OPEN!

NOTE: You must have a fully paid, active (not lapsed) Family with Children membership to register for sailing school classes. If you need to renew your membership, you will see a message in the bottom right corner of your screen. 

We are hopeful that this season will be more typical than the summer of 2020. We recognize that COVID conditions and restrictions can change quickly. We will be making adjustments as necessary to keep us both safe and in compliance with regulations. 

Sailing School Overview                             

The Chatham Yacht Club runs a sailing school program with approximately 100 students each year.  We run classes 5 mornings / week for 8 weeks during the summer. For 2021, classes will run from June 28 - Aug 20. We are extremely hopeful that Crew, our beginner class will once again be taught in Beetle Cats this summer.  Because many of our 2020 Crew class sailors are able to sail in optis, we are including a section of Advanced Crew which will generally be taught in Optis. (Due to weather and other conditions, these sailors may sometimes sail in Beetle Cats.) Typical students spend 1 to 2 summers in the crew class. Seaman, our intermediate level classes are taught in Optis. We offer two or three levels of opti classes depending on student ability. In these seaman level classes, students begin by learning how to single hand a sailboat (sailing it alone) and progress to learning racing tactics in the optimist. In addition to our Seaman level Optimist classes, we have a Seaman level Sunfish class which allows students to sail in pairs. This is our Seaman Recreational class, which has a focus on sailing rather than racing. Our Helmsman level classes are taught in 420s.  Most summers we offer both Helmsman Racing and Helmsman Recreational classes. 

The Chatham Yacht Club Sailing School is available to members only. If you are interested in becoming a member, please contact Karen Taylor at

Sailing School Progression Chart


Weekly Overview of Class Schedules for 2021



We are planning to start all morning classes together, at 9:00 am. On Monday, Tuesday and Friday, class will end at 12:00. On  Wednesdays and Thursdays sailors should bring a lunch and plan to eat outside before a sailing school race. The approximate end time on these days is 1:30. 


Due to Covid, we do not plan to spend time inside the clubhouse during the 2021 season. If the weather looks bad for sailing (excessive wind or rain/thunderstorms), we may need to cancel. Check you email for the latest. The goal is to send something by 8:00am if cancellation or postponement is necessary.

Click here for CYC Parking and Access details

See below for information on "What to Bring" to class each day.

See above for Sailing School Progression, what class leads to which boat?


All members of the Chatham Yacht Club are encouraged to take part in their club by volunteering during the summer sailing season, mid-June to late August. The friendly camaraderie that results is vital to the continued success of CYC, which has been dedicated to the development of sailors since its founding in 1921.   

Volunteer opportunities

2021 CYC Sailing School Staff:

Program Director:
Assistant Program Director:

420 Race Team Head Coach,

Crew Class Leadership Advisor

Jeff Howell
Ashley Dart

420 Race Coaches: 

Hank & Will Bailey

Opti Race Coach: 

Katelyn McGauley

Crew Class Director: Schuyler Bartlett
Crew Class Assistant Director: Karina Lamoreux
Recreational Sailing Director:

Caitlin Fitzmaurice

Opti Advanced:

Katelyn McGauley

Opti Intermediate:  

Opti Beginner Director:

Calder Robbins

Grace Gunsalus

Helmsman Director: Hank & Will Bailey



Amelia Gassner

Sara Lennox

Zoe Maggioni

Julia Szymanski

Race Team: 

Ashley Dart

Hank Bailey

Will Bailey


Tucker Lamoreux

Fleet Captain:

Calder Robbins

Staff Bios

Junior Instructors - Crew:

Catherine Dickson

Julia Scipione

Sally Wray

Instructors - Opti:

Chad Bartlett (beginner)

Cody Lamoreux (advanced)

Sophie Maggioni (intermediate)

Cailyn Murphy (beginner)

Instructor - Recreational:

Coco Fitzmaurice

CYC is excited to be working with US Sailing this summer with their new application for sailing skill development called Skill Up. Everyone in Crew, Opti Beginner, Opti Intermediate, Opti Advanced, Sunfish and Helmsman were given a youth US Sailing Membership as part of your CYC class registration.

The parents should have received an email from US Sailing with your child's US Sailing number as well as requesting additional information. Please take the time to update your membership information. Your child will most likely receive stickers from US Sailing if they have your mailing address.

Skill Up is an App that you can download onto your phone. You can access what your child is learning by entering in their US Sailing Number. Please look at the following link with additional information.

What to bring?

Sailing school is held every day, RAIN or SHINE! 

It is important that each child comes prepared. Remember to mark items with your name!

Please have your child WEAR to Sailing School every day :

  • Swimsuit
  • T-shirt and Shorts (clothing to cover up during walk through Eastward Ho! Golf course)
  • Closed-toe shoes (crocks, old sneakers, or water shoes)

Please have your child BRING to Sailing School every day :

  • Life Jacket (to be worn at ALL times on dock, on float, in launch and in sailboats)
  • Towel
  • Sunscreen
  • Hat / Visor / Sunglasses Extra t-shirt and shorts
  • Sweatshirt / rain jacket
  • Lunch on Sailing School Race Day (Wednesday or Thursday) 
  • Personal water bottle (please use a refillable bottle to cut down on global waste).

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!

Powered by Wild Apricot Membership Software