2021 Sailing Program


Our 2021 Kids Group Sailing Program sails Monday-Friday. Private lessons are also available for all ages & ability.

This year we have invested heavily in our sailing program. Our goal is to prepare our children for a safe, knowledgeable future in racing and/or casual sailing.

New for 2021: 

  • new, completely refurbished float (moored dock)
  • operating out of a new location (Quammox Landbank property on Katama Bay)
  • refurbished 420s
  • new chase boat

⇒ Our group sailing lessons for children are offered Monday through Friday from 9 am to noon from July 5 to August 20.

⇒ Classes are $50 per day.

Private lessons are available at noon on Tuesdays, Thursdays & Fridays for all ages and ability @ $100 per hour, for up to two people

⇒Ready to get started? Follow these three steps …

  1. Please email chappyccenter@gmail.com with your desired dates
  2. Once your preferred dates are confirmed, we ask that you visit the online store and pay within 24 hours of your confirmed dates. Our program is in high demand!
  3. Email the medical & liability forms to chappyccenter@gmail.com


Things to know: 

  • A CCC Membership is required before registering for our sailing program CLICK HERE
  • Participants will be met at the Quammox location (Landbank property on Katama Bay)
  • We currently have a maximum capacity of 6 children per day in our group lessons
  • Masks are required for those not vaccinated
  • Your child must bring their own life jacket & water shoes. Long hair must be tied back.
  • Unless otherwise approved by the CCC program manager, the minimum participant age is 8
  • Liability & Medical Forms and Payment must be received by the CCC office before first lesson.

    Medical Form
    Liability Form



As you all know the island delivers its fair share of weather conditions in the form of fog, too much wind, too little wind, high seas and more. The program office and instructors check conditions daily and make decisions to keep our participants safe.

  1. In the event we have to cancel a private lesson due to inclement weather, we will make every effort to reschedule at a mutually convenient time. 
  2. If we deem the morning unsafe to carry on with our kids sailing program, we will have a “dry deck” lesson as an alternative. In these sessions children will learn boating safety skills, knot tying, weather patterns, rigging, and more. Dry deck sessions may be conducted on the beach, on the float, or at the center. 


Unfortunately we are unable to offer refunds, but we are happy to apply your payment to another program or consider it a donation to the CCC.


2021 Sailing Instructor

The CCC is very fortunate to have met both Anna and Maeve. We look forward to another successful, new & improved, 2021 sailing program.

Maeve Fiske has been on the water since she was five years old. She started white water rafting and kayaking with her Mom on the Deerfield River. By age ten she was introduced to opti sailing at Vineyard Haven Yacht Club (VHYC). Since then she progressed to competing in c420 regattas on a national level. During her tenure at VHYC, she taught sailing for opti’s, c420s, and windsurfing. Maeve also sailed sonars, c420’s, 470’s, 29er’s, and J100’s. When not sailing, she is a competitive ski racer with Stratton Mountain School as well as a Crossfit Athlete.

In addition, Maeve has gone to a multitude of regattas ranging from SMSA to Triple Crown. At these smaller SMSA regattas, she placed in the top 10 many times throughout the years and in the last summer consistently in the top 5. Last summer she placed 14th at the North American championships! Maeve has also received a multitude of awards showing her character. These include: most improved sailor, maintenance, seamanship, perseverance, crew award, and the most improved female at the yacht club.

Maeve is currently attending Babson College. One last highlight… she’s the sister of Anna Flaherty who taught for us last year! (there is a rumor Anna may pop in and join Maeve later in the season)

Anna Flaherty, a recent graduate of Hobart and William Smith Colleges where she was a four year varsity member of the HWS sailing team. She was honored by the international Collegiate Sailing Association as an All-American crew and a four time Academic All-American. She grew up sailing at the Vineyard Haven Yacht Club and worked at Edgartown Yacht Club for three summers teaching intermediate Opti, recreational sailing, and the Opti race team. Anna has competed in club 420’s and Fj’s all over the United States, from Buzzards Bay to Corpus Christi, TX. This fall she will be moving to Burlington, VT to attend the Post-Baccalaureate Pre-Medical Program at University of Vermont in pursuit of a medical degree.


Main sheet - Alex Dunbrack