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Chatham Yacht Club

TEACHING LOVE OF SAILING ON PLEASANT BAY SINCE 1921

sailing school

CHATHAM YACHT CLUB SAILING SCHOOL

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!  

SAILING SCHOOL 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 2025, classes will run from June 23 - Aug 15.

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  membership@chathamyachtclub.org.


SAILING SCHOOL PROGRESSION CHART

Which sailing school class leads to which boat?



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WEEKLY OVERVIEW OF CLASS SCHEDULES

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A note about SAILING SCHOOL RACES:

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

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SAILING SCHOOL BEHAVIOR EXPECTATIONS

It is our expectation that all sailors will be positive community members, treating their peers, instructors, and equipment with respect. Because of real safety issues, sailors need to listen and follow instructions. If sailors are unable to participate constructively and safely, they may need to remain on shore, and the families will be notified to help resolve the issue. If you know of strategies that have helped your sailors in the past, please let us know so that we all have a productive and fun summer.


2025 CYC SAILING SCHOOL STAFF

Program Director: Schuyler Bartlett

420s  
 420 Race Coach: Ryan McGauley
 Helmsman Class Co-Directors:

Chad Bartlett

Tucker Lamoreux

 Helmsman Class Instructors:

Sophie Dart

Alex Wesp

Max Wesp

 Optimist  

 Opti Race Team Co-Coaches &

 Opti Advanced Class Co-Directors:

Cody Lamoreux

Cailyn Murphy

 Opti Advanced Instructor:  
 Opti Intermediate Class Co-Directors:

Amelia Gassner

Sarah Lenox

 Opti Intermediate Instructors: Jessica Scipione
 Opti Beginner Class Director: Julia Scipione
 Opti Beginner Class Instructors: Jaime Eslick
  Harrison Kintz
 Beetle Cat  
 Crew Class Co-Directors Brooke Bartlett
  Rosie Benson
 Crew Class Instructors


 Crew Class Jr. Instructors

Sam Bartlett

Eli Gertsberg

 Sunfish  
 Recreational Sailing Class Director: Julia Szymanski
 Recreational Sailing Class Instructor:  
 Recreational Sailing Class Jr. Instructor:

Brooke Bishop

Ada Hubbell

 Substitute Instructors  
 Substitute Instructors:

Chase Berner

Maret Downs

Annamarie Hubbell

Lucy Lipson

Jake Parker

Leah Parker

Lucy Richmond

Zach Wesp



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VOLUNTEER

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.

https://www.ussailing.org/education/youth/youth-development/

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Our Summer 2025 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 EVERYDAY:

  • 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 EVERYDAY:

  • 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).
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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!

ACCESS TO CYC

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.

Mid-day

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 & 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 & 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.

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Sailing School & Racing Calendar

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


Upcoming events

    • 23 Jun 2025
    • 11 Aug 2025
    • 8 sessions

    This is  a calendar placeholder.  For more detailed information please see the Sailing School page. 

    Sailors in the Advanced Opti class are automatically part of this class, with no additional cost.

    The Opti Race Team class joins the Advanced Opti class once each week on Monday mornings. 



    • 23 Jun 2025
    • 14 Aug 2025
    • 24 sessions

    Sunfish Recreational Sailing Class - 3 x per week

    This is  a calendar placeholder.  For more detailed information please see the Sailing School page. 


    • 23 Jun 2025
    • 14 Aug 2025
    • 24 sessions

    Advanced Opti / Opti Race Team Sailing School Class 

    This is  a calendar placeholder.  For more detailed information please see the Sailing School page. 


    • 23 Jun 2025
    • 14 Aug 2025
    • 24 sessions

    Beginner Opti is also known as "Opti B".

    This is  a calendar placeholder.  For more detailed information about this class please see the Sailing School page. 

    • 23 Jun 2025
    • 15 Aug 2025
    • 24 sessions

    Intermediate Opti, also known as "Opti I"

    This is a calendar place holder.  Please see the Sailing School page for more detailed information. 

    • 23 Jun 2025
    • 15 Aug 2025
    • 24 sessions

    Crew Class 

    This is a calendar place holder.  For more detailed information please see the Sailing School page. 


    • 23 Jun 2025
    • 14 Aug 2025
    • 24 sessions

    Sunfish Recreational Sailing Class - 2 x per week M/T T/TH

    This is  a calendar placeholder.  For more detailed information please see the Sailing School page. 

    Students who would like to sail in the Sunfish class in addition to another class can use this 2 day / week option. For example, If your child will also enroll in Helmsman they would join the Sunfish class on Mondays and Thursdays. 


    • 23 Jun 2025
    • 15 Aug 2025
    • 24 sessions

    This is a calendar place holder.  For detailed information, please see the Sailing School page.

    The 420 Race Team meets on Monday, Thursday and Friday afternoons. Team Members hone racing techniques and learn advanced tactics in 420s. Sailors also learn and master team racing in 420's. The environment of the 420 Racing Team, while not without a focus of fun and entertainment, is more geared towards competitive racing and drills during each practice. 420 Racing Team sailors compete in team racing events against other Cape Cod yacht clubs, other SMSA 420 Race Teams, and are sometimes selected to represent CYC in various other Southern Massachusetts Sailing Association (SMSA) and United States Sailing Association (USSA) events.



    • 23 Jun 2025
    • 11 Aug 2025
    • 8 sessions

    Adult Sailing -Mondays from 2-4:30PM

    This is a calendar place holder.  For more detailed information please see the Sailing School page. 


    • 24 Jun 2025
    • 15 Aug 2025
    • 24 sessions

    Helmsman Class.
    This is a calendar placeholder.  Please see the Sailing School page for detailed information. 

    • 24 Jun 2025
    • 12 Aug 2025
    • 8 sessions

    On Tuesdays, 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.

    • 25 Jun 2025
    • 13 Aug 2025
    • 8 sessions

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

    • 25 Jun 2025
    • 13 Aug 2025
    • 8 sessions

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

    • 26 Jun 2025
    • 14 Aug 2025
    • 8 sessions

    On Thursdays, the Sailing School race for that day's students begins approximately at 12:30 pm.  Family members are welcome to come watch the races!

    • 28 Jun 2025
    • 16 Aug 2025
    • 8 sessions

    This is a calendar placeholder.  Please see the website for more detailed information.

    In addition to our Monday afternoon Adult Sailing class, we will offer a Saturday morning beginner class taught by our paid sailing school instructors (generally teenagers). The Saturday class will offer the same curriculum as the Monday class. 


    • 28 Jun 2025
    • 16 Aug 2025
    • 8 sessions

    The Saturday schedule has been modified for this year - reflecting the members desire to have two races but to not be at CYC too long. Just like Tuesdays, 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.

    • 30 Jul 2025
    • 08:00
    • 31 Jul 2025
    • 16:00
    • CYC

    CYC is hosting the 2025 and 2026 GILL Trophy for SMSA.  This is the SM Sailing Junior Women's Championship.   Volunteers welcome to assist hosting this event!


    • 02 Aug 2025
    • 03 Aug 2025
    • Chatham Yacht Club

    The oldest free regatta on Pleasant Bay since 1921!

    • 16 Aug 2025
    • 15:00 - 17:00

    CYC Closing Meeting and Awards; All are welcome and encouraged to attend.

    • 17 Aug 2025
    • CYC

    Join us and help put CYC to bed for the off season.  CYC runs on volunteers and we can not do this without your help.  See you then!

Past events

04 Jul 2025 4th of July Race
28 Jun 2025 Opening Meeting
28 Jun 2025 Saturday Races Begin
28 Jun 2025 Coast Guard Auxiliary Class
23 Jun 2025 Sailing School Begins!
16 Jun 2025 CYC Staff "Work Week"
14 Jun 2025 Clubhouse Opening
25 May 2025 Clubhouse mini-opening
18 Aug 2024 Clubhouse Closing
17 Aug 2024 Closing Meeting and Awards
03 Aug 2024 Chatham Regatta
22 Jul 2024 DSNAC
04 Jul 2024 4th of July Race
29 Jun 2024 Opening Meeting
26 Jun 2024 Crew "B" (W,F)
15 Jun 2024 Clubhouse Opening
05 Aug 2023 Chatham Regatta
04 Jul 2023 4th of July Race
06 Aug 2022 Chatham Regatta
04 Jul 2022 4th of July Race
07 Aug 2021 Chatham Regatta
06 Aug 2021 Centennial Gala 2021
06 Aug 2021 Baybird Open House
31 Jul 2021 Leo J. Telesmanick Championship Regatta
31 Jul 2021 NEBCBA Centennial Celebration Dinner and Meeting
31 Jul 2021 Telesmanick Event Registration
04 Jul 2021 4th of July Race
22 Jun 2021 NEBCBA Membership
20 Jun 2021 Telesmanick Gear Pre-Order
01 Aug 2020 Chatham Regatta
04 Jul 2020 4th of July Race
15 Aug 2019 Barnstable Green Fleet Opti
13 Aug 2019 Beverly Jr
07 Aug 2019 Hyannis Youth Invitational
03 Aug 2019 Chatham Regatta
02 Aug 2019 Commodore's Buffet 2019
31 Jul 2019 SMSA Team Racing Championship
29 Jul 2019 CJ Buckley
26 Jul 2019 Hyannis
24 Jul 2019 Wianno Opti Regatta
22 Jul 2019 SMSA Gill Trophy
20 Jul 2019 Falmouth Regatta
18 Jul 2019 Orleans Outer Cape
15 Jul 2019 Stone Horse Opti
15 Jul 2019 Vineyard Haven Jr
09 Jul 2019 Bass River
08 Jul 2019 West Dennis
06 Jul 2019 New Bedford Jr
04 Jul 2019 4th of July Race
01 Jul 2019 Stage Harbor Opti Regatta
13 Aug 2018 Barnstable Green Fleet Opti
09 Aug 2018 SMSA Team Racing Championship
08 Aug 2018 Hyannis Youth Invitational
04 Aug 2018 Chatham Regatta
02 Aug 2018 C420 NAs/BB C420 Championship
30 Jul 2018 CJ Buckley
27 Jul 2018 Hyannis
25 Jul 2018 Wianno Opti Regatta
23 Jul 2018 SMSA Gill Trophy
21 Jul 2018 Falmouth Regatta
19 Jul 2018 Orleans Outer Cape
16 Jul 2018 Stone Horse Opti
10 Jul 2018 Bass River
09 Jul 2018 West Dennis
06 Jul 2018 Stage Harbor Opti Regatta
04 Jul 2018 4th of July Race
14 Aug 2017 Barnstable Green Fleet Regatta
09 Aug 2017 Hyannis Youth Invitational
08 Aug 2017 420 Nationals
05 Aug 2017 Chatham Regatta
04 Aug 2017 Commodore's Buffet
31 Jul 2017 CJ Buckley Team Race Regatta
28 Jul 2017 Hyannis Regatta
26 Jul 2017 Wianno Opti Regatta
24 Jul 2017 SMSA Gill Trophy
17 Jul 2017 Stone Horse Opti Regatta
17 Jul 2017 Vineyard Haven Jr. Regatta
17 Jul 2017 Area A Qualifier (Bemis & Symthe)
11 Jul 2017 Bass River Invitational
10 Jul 2017 West Dennis Invitational
06 Jul 2017 Stage Harbor Opti Regatta
04 Jul 2017 4th of July Race
30 Jun 2017 Cummings Cup
09 Aug 2016 Hyannis Youth Invitational
09 Aug 2016 USODA New England Championships
06 Aug 2016 CYC Regatta
01 Aug 2016 Barnstable Green Fleet Regatta
30 Jul 2016 Hyannis Regatta
27 Jul 2016 Wianno Opti Regatta
18 Jul 2016 Stone Horse Opti X-Treme Regatta
12 Jul 2016 Bass River Invitational
11 Jul 2016 West Dennis Invitational
07 Jul 2016 Stage Harbor Opti Regatta
04 Jul 2016 July 4th Race
01 Jul 2016 Cumming Cup
24 Jun 2016 420 New Englands (Area A Bemis Qualifier) Pleon YC

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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