Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921

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2024 Sailing School Registration 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. 

CYC also offers Adult Sailing!  

Adult Sailing Registration

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 2024, classes will run from June 24 - Aug 16.

Crew, our beginner class, is taught in Beetle Cats with an instructor and 2-4 students in each boat. 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.  Some 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

Sailing School Progression Chart

Which sailing school class leads to which boat?


Weekly Overview of Class Schedules 



On Wednesdays and Thursdays, the Sailing School race for that day's students begins approximately at 12:30 pm.

The Wednesday Junior Races - which are open to any CYC sailor (all skippers have to be under the age of 16) begin at 2:00 pm with starts for 420s, Sunfish, Optimists, and Beetle Cats. Family members are welcome to come watch the races!

*Tuesday Series Races: This series is not part of Sailing School, however our sailors are welcome to compete. We begin racing at 1 pm and run starts for 420s, Sunfish, Optimists, and Beetle Cats. We run two starts for each class with each start being a different season series. The second Beetle Cat start is our Women's Series. Even if you do not have one of these boats, you are welcome to come watch, or help patrol or help run the races.

Saturday Series: We begin racing at 1 pm and will run a second race immediately following the first. Both races will count for the same Saturday series. Because we are running two races, we will NOT try to make up any races that are canceled due to weather (etc.). On the first and last Saturday of the season we will only run one race because of the opening and closing meetings. On Saturdays, we run starts for C-14s, Lasers, 420s, Sunfish, Optimists, and Beetle Cats. We also plan to have a series for the Adult Beginner class as a C-14 Green Fleet.

CYC Racing Information

CYC Season Awards & Trophies (awarded to all ages!)

For racing questions, please feel free to contact your program director, Schuyler Bartlett or our racing committee : Marshall Bartlett & Ted Dickson


2024 CYC Sailing School Staff:

Program Director:

Schuyler Bartlett


420 Race Coach: 

Ryan McGauley

Helmsman Class Co-Directors:

Chad Bartlett

Tucker Lamoreux


Opti Race Team Co-Coaches &

Opti Advanced Class Co-Directors:

Opti Advanced Instructor:

Cody Lamoreux

Cailyn Murphy

Brooke Bartlett

Opti Intermediate Class Director:

Julia Scipione

Opti Intermediate Instructor:

Max Wesp

Opti Beginner Co-Directors:

Opti Beginner Class Instructor:

Amelia Gassner

Sarah Lenox

Sophie Dart

 Beetle Cat  
Crew Class Director:

Catherine Dickson

Crew Jr. Instructors: Rosie Benson

Henry Bishop

Jaime Eslick

Harrison Kintz

Jessica Scipione

Alex Wesp

Recreational Sailing Class Co-Directors:

Coco FitzMaurice

Julia Szymanski

Recreational Sunfish Instructor:



 Substitute Instructors: Sam Bartlett

Eli Gertsberg

Ada Hubbell



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

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.


Our staff is the foundation of our program. This year, we have a mixture of returning and new staff. The 2024 instructors are racing enthusiasts, sportsmanlike competitors, and passionate teachers. They are a truly inspirational group for younger sailors to learn from.

We are so lucky to have our 420 Race Coach, Ryan McGauley return to CYC. Ryan is a highly accomplished sailor and has just completed his freshman year at BC, sailing on the Boston College Sailing Team. He has sailed for Team USA in Optimists as well. With knowledge of both skippering and crewing, fleet racing, and team racing, we could not ask for a more versatile and impressive teacher.

Tucker Lamoreux will lead our Helmsman 420 class with help from Chad Bartlett. These two instructors worked together last summer and will continue to inspire their students to love racing as much as they do.

Cailyn Murphy and Cody Lamoreux will be the Opti Co-Race Coaches and lead our Advanced Opti Class. These sailors dominated Cape Cod Opti regattas when they were Opti sailors, and they are eager to now be on the teaching side of things. They led these classes last summer to great success and are eager to return with even more knowledge. Joining Cailyn and Cody in the Advanced Opti classes will be CYC instructor Brooke Bartlett.

Julia Scipione will lead our Intermediate Opti Class with help from instructor Max Wesp. Both instructors have taught in Optis for a few summers and have ample knowledge to pass on. Amelia Gassner and Sarah Lenox will lead our Opti Beginner Class with instructor Sophie Dart. Amelia and Sarah have the patience, enthusiasm, and kindness it takes to run this essential curriculum. Our Opti students are lucky to benefit from the expertise of our outstanding coaches!

Catherine Dickson is the enthusiastic leader of our Crew Class. This beginner class sails in borrowed Beetle Cats, generously donated by CYC members. Catherine has been teaching Crew for many summers, and the students adore her. Her creativity and ability to connect with all students make her perfect for this role. The students will also receive individual attention and feedback from our fantastic junior instructors: Rosie Benson, Henry Bishop, Jamie Eslick, Harrison Kintz, Jessica Scipione, Alex Wesp.

Our growing Recreational Program, which sails in Sunfish, will be run by Julia Szymanski and Coco FitzMaurice. These instructors have worked with Sunfish for many summers and are extremely skilled in creating exciting lesson plans fit for all levels of sailors. They will no doubt excel in encouraging the learning of sailing in a non-racing environment.

Finally, our classes would not be complete without the help of our Substitute Instructors: Sam Bartlett, Eli Gertsberg and Ada Hubbell.

Our Summer 2024 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.

As program director, my goal is to foster a safe, fun, and inclusive environment for every sailor. I hope to encourage learning, growth, sportsmanship, and friendship. Let’s go sailing!

-Schuyler Bartlett

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).

Getting your boat to CYC:

No boats or sailboards may be carried over the hill to be launched at CYC.

Launching may take place at Jack Knife Harbor, the Town Landing on Crow's Pond, Ryder's Cove or in Round Cove. Please pay attention to any permitting needs for launching any boat.

Transportation of 420s and Optis over the hill for the purpose of attending regattas during the summer may occur ONLY before sunrise and after sunset per our lease with Eastward Ho! (If you have purchased an Opti for your sailor and are depositing or removing your Opti for the season, these same Eastward Ho! requirements apply.

Thank you in advance for your cooperation!


CYC Parking

The parking lot configuration allows for multi-directional Fox Hill Road access from three points as illustrated in the diagram below. It is essential that all CYC traffic use the third entrance on Fox Hill road to minimize the access traffic and pedestrian hazards in the other parts of the parking area.

The added parking has improved parking but we, EHCC and CYC, need to continue to optimize on the available parking with the following actions;

Sailing School morning classes

CYC instructors will be available to help students to and from the CYC club house so parents can enjoy the convenience of “drop and go” noted by the yellow cross-hash area. Before 11:30 am, parking may be available on a first-come, first-serve basis in the designated area, highlighted in green box, for parents to bring their children to classes, meet the instructors and fellow parents. Please be aware this area is not exclusive to CYC but shared with EHCC. If there is a shortage of parking spaces in the designated area, please park on the shoulder of Fox Hill Rd. “Pickup and go” will also be available for your convenience at the conclusion of morning classes at the Pick-up spot shown in the diagram. This is a safer and shaded location where our students can be ready for pick-up.


Parking begins to get busy around 11:30 when Eastward Ho! Lunch service begins. After 11:30, We ask that CYC members park on the Fox Hill road shoulder during lunch if the north lot is busy.

Afternoon classes and races

Due to the limited amount of parking spaces, Parents are encouraged to enjoy the convenience of “drop and go” where appropriate for the children. Parents who would like to see your kids in action during the afternoon races can check for available parking spots in the designated (green) area after 2 PM. If there is a shortage of parking spaces at any time, please park on the shoulder of Fox Hill Rd.

Eastward Ho! will have parking lot attendants available to assist with traffic flow and direct CYC members to the designated (green) area. Please don’t hesitate to speak with them if you have any questions or need assistance.

As always, safety is paramount as we balance convenience and consideration for a shared parking resource with our friends at Eastward Ho!

Thank you in advance for your cooperation!

Courtesy and Safety on the Golf Course

An average golf ball leaves the tee traveling 115 mph or more, and our path to CYC takes us right in front of the first tee. Adults and children need to take care as they cross in front.  Eastward Ho! has provided a fence to protect us.  CYC members should stop at the edge of the fence, look and assess the situation.  Always wait while golfers are teeing off, but if the golfers are waiting, they may signal it is safe to cross. Be aware as you approach the ninth green as well, since it is just beyond our path.

Eastward Ho! and CYC have a great working relationship, but it depends on CYC members being courteous to and respectful of the golfers.  Please wear shirts and shoes when crossing the hill, and do not use your cell phone.  It is best to be quiet when golfers are on the 9th green.  You may stop and wait, or move quietly by, but try not to distract those focusing on their putts.


Sailing School & Racing Calendar

To see additional CYC events, please use the calendar tab on the menu.

Month: July 2024

Jul 1
Aug 1

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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