Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921

COVID-19 Update:

The leadership team at CYC is working to adjust to our new uncertain world. We will be working within the guidelines of the state of Massachusetts as well as both state and local health agencies. As of now, we do not know exactly what the 2020 season will look like, but we know that we all would like our summer to include some sailing!

For now, we are asking sailing school families to please register for classes for their children if they plan to participate in sailing school this season, but please do not pay for the class yet. All of our classes ask for offline payments (ie, not online credit card payments). Given class registrations, limitations of boat use, social distancing policies... etc, we will be making adjustments to our program, and possible our associated costs as well. For example, if we cannot hold a class 3 days/week and opt for 2 days/week, we would adjust the cost of that class.  

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 2020, classes will run from June 29 - Aug 21. Crew, our beginner class, while normally taught in Beetle Cats, will be taught in Optis this year because of social distancing regulations. Students in the crew class will come to sailing school two days a week, where they will receive closely individualized instruction both on shore and in close proximity to the beach  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 2020


Weekly Overview of Class Schedules (2020)


For 2020 Sailing School begins with a staggered start and finish to minimize exposure and practice social distancing as much as possible.

What time do I pick up my child??

Please see the chart above.  Sailors are unable to remain at the clubhouse when they are not actively participating in sailing school or designated races.

For the 2020 season,  there will be no ability to stay or linger at the clubhouse. 

Sailors are unable to stay for lunch and snacks will not be served.

If Sailors wish to return for the afternoon races according to the skill chart above, they must return home between sailing school and race start times. 

Face masks / face coverings must be worn at all times when on land.

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.   

2020 UPDATE: Volunteers will be needed to help keep CYC safe this season.  Please check with the CYC director or look for our sign up sheets (to come). 

Refreshments & Social Events

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

Staff Bios

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

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!

2020 UPDATE : Because we are unable to use the clubhouse for shelter on inclement weather days; there may be days when sailing school is canceled or cut short.  Please monitor your email for any important updates.

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)
  • 2020 UPDATE : Face masks or protective face coverings are required to be in use at all times when on land.

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) 2020 UPDATE:  Sailors are unable to stay at the clubhouse when not on water and will not have lunch at CYC.  Unfortunately, snacks will also not be available.
  • Refillable water bottle

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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