Meet the 2019 Sailing School Team

 Chris Beard: Program Director

 (Centerville, MA)

Chris is returning for his 3rd season as Program Director. Over the past two summers he has thoroughly enjoyed working with the outstanding Stage Harbor instructors and getting to know the wonderful parents and children in the sailing program. Chris lives year round on Cape Cod in Centerville and teaches high school history at Sturgis Charter Public School in Hyannis. Chris competes in PHRF ocean racing on Cape and enjoys spending vacation time with his family on Mount Desert Island, Maine in the summer.



Kelsey Shakin:  Assistant Program Director and Head 420 Coach
(Boston, MA)


Kelsey returns to SHYC for her 9th summer on staff. She has just graduated from Roger Williams University, studying Marine Biology and Public Health.  At RWU, Kelsey was a member of one of the top nationally ranked sailing teams in the country, as the A Women's skipper and captain. Kelsey is very excited for the upcoming season at SHYC and everything the summer has to offer!



 Ally Kraus: Marketing, Communications and Operations Coordinator
 (Belmont, MA)

Allison is a student at Fairfield University where she majors in Finance and minors in Mathematics.  She competes on the sailing team during fall and spring semesters. This summer will be her 14th year sailing. Allison loves going to the beach and spending time in Chatham and cannot wait to start her 7th year as a members of SHYC staff.


 Charlie Hibben: 420 Coach


Charlie finished his freshman year at Tufts University. He is both a part of the Olympic Development Program team and the Tufts Sailing Team. He learned to sail at Barnstable Yacht Club. When he graduated to 420s, he started racing out of Wianno Yacht Club. He has many notable achievements in many classes including winning the Club 420 New England Championships at age 15, placing top 3 at High School Nationals three times, qualifying for the one US spot for the 29er class in the 2018 Youth World Championship, and helping that team win USAs first Nations Trophy. Charlie is excited to help every sailor reach their full potential this summer. 



Olivia Gonzalez: Coach
(Islamorada, FL)

Olivia will be a junior at the College of Charleston, she is also a graduate of St. George's School in Newport, RI. Sailing is her strongest sport and her passion. She learned to sail when she was six years old at SHYC and continued year-round back home in Florida. Her favorite memories are spending her summers in Chatham and growing up sailing for SHYC. Olivia is excited to pass on her love of sailing and fun on the water this summer!


 Cailin Gensler: Opti Coach
 (Winchester, MA) 

Cailin is returning for her 7th summer working at SHYC and cannot wait to be back on the water. Cailin’s interest in sailing was sparked at a young age when she joined the SHSS. Returning every summer, Cailin grew into a knowledgeable sailor. She had the opportunity to sail for the St. George’s School sailing team in high school, which is where she really fell in love with the competitive racing aspect of sailing. After graduating in 2017, Cailin now attends Hobart and William Smith Colleges where she is a double major in French and English. The HWS sailing team is one of the top ranked sailing teams in the country. Cailin has had the opportunity to participate on both the coed and women’s team at HWS. Being able to compete on the college level in any sport is an achievement and Cailin would not have had this opportunity if it was not for the instruction and knowledge she received at SHYC. Cailin loves the memories she has from the sailing school when she was a little girl; she hopes that she can help create lasting memories just like her instructors did for her and inspire more students to compete at higher levels of sailing.    


 Zoe Carlson: Opti Coach

 (Boston, MA)

Zoe Carlson grew up in Boston and has spent every summer of her life in Chatham.  She is a rising sophomore at Claremont  McKenna College in southern California.  Zoe is thrilled to be returning in 2019 for 6th summer working at SHYC. She will be an Opti coach with her former 420 crew, Cailian Gensler.  She will also be working at SHYC in the mornings as a Senior Instructor. Zoe U.S. Sailing level 2 certified instructor and is looking forward to spending another summer on Stage Harbor.  In her free time, she enjoys biking, instructing/practicing yoga, volleyball and being on and around the water.



 Jack Evans:  Senior Instructor 

(Charlestown, MA)  

Jack just finished his freshman year of college at Elon.  He is from Charlestown Massachusetts.  This summer will be his fourth year on staff.   






 Hammond Hearle:  Senior Instructor 

Hammond is a rising sophomore at The College of William and Mary planning on majoring in International Relations and Business. She is excited to return for her fourth summer as an instructor and twelfth summer sailing at SHYC. Hammond sailed for William and Mary’s sailing team this year, and played soccer and lacrosse throughout high school. She cannot wait to return to Chatham this summer!




Dorothy Waskow:  Senior Instructor

Dorothy is a rising sophomore at Tufts University. She started sailing Optis at the age of seven and moved to double handed boats such as Snipes, and Lightnings, and 420s. Dorothy is currently a crew on the Tufts University sailing team. She also has a lot of experience working with kids. She has been a camp counselor for the past two summers and worked in a Kindergarden-2nd grade classroom in high school. Dorothy can't wait for summer to start and is excited to be working at SHYC!




Kerry Sullivan:  Senior Instructor

(Houston, TX)

Despite being raised in Houston, Texas, has grown up sailing at SHYC, and began teaching at the age of 15. Kerry will be a rising junior at Muhlenberg College in Allentown, Pennsylvania where she is studying theatre and dance. Unfortunately, there is no water near campus, so sailing proves to be difficult; instead, she spends her time outside the classroom performing and teaching theatre and dance in the greater Allentown and Philadelphia area. She is looking forward to her fall semester as she will be living in New York City, participating in a theatrical study away program. Kerry will be spending the beginning of her summer performing at a summer stock theatre, but will be back on the Cape in August to finish up her summer at SHYC. 

 Emma Leary:  Instructor

 (Bethesda, MD)

Emma will be returning as an Instructor at SHYC and can’t wait to be back in Chatham. She will be attending her first year at Dartmouth College this fall and recently graduated from Georgetown Day School in Washington, DC. She has been sailing at SHYC since she was 8 years old and will continue to sail in college on the Dartmouth Sailing team. Emma looks forward to her last season on the SHYC 420 Race Team, being on the water with the kids, and teaching STEAM lessons in Shore School! 



 Cat Shakin: Instructor
 (Boston, MA)

Cat Shakin is from Boston MA! She recently graduated from Tabor Academy in Marion, Massachusetts where she was a member of the varsity sailing team for three years. With Tabor, she participated in six New England and three National High School Championships. She has also been sailing at SHYC since she was six years old, making this her thirteenth summer in the program! She has also sailed competitively for SHYC since she was 11. Cat looks forward to continuing her sailing career at Boston University in the fall and she is very excited to see everyone back on the water for this summer!

 Hayden Earl: Instructor 

 (Boston, MA)

Hayden is current member of the St. Georges sailing team and loves working with the kids at SHYC.





 Henry Hearle: Instructor       
 (Boston, MA) 

Henry is excited to return for his 4th summer working at SHYC. He will be a senior at Phillips Academy Andover in the fall, where he participates on the squash and crew teams. Henry is looking forward to another amazing summer at Stage Harbor!





 Alex Gonzalez: Instructor

 (Islamorada, FL)

Alex will be a senior this fall at Coral Shores High School in the Florida Keys where he was captain of the varsity sailing team for three years. Alex sails competitively year-round in Florida where he sailed Optis, 420's and now Lasers.  He is excited to be back at SHYC working with the kids for another great summer on the water!




Will Lucy Jr: Instructor 

(Chester, NJ)

Will is in his second year working at SHYC. He is a rising sophomore at St. Mark’s School in Southborough, MA. He originally is from Chester, NJ but has been spending his summers in Chatham for as long as he can remember. Will has sailed for the past six years, competitively sailing both optis and 420s in many regattas and still races 420s. Will looks forward to the coming years at SHYC as well as teaching kids to sail for fun and for sport.


 Drew Donahue: Instructor-in-Training

Drew is returning for his 9th summer at SHYC, and his first summer as an official member of the staff. He attends Wellesley High School in Massachusetts, and will be a sophomore after the summer is over. Aside from sailing, Drew enjoys running for the cross country and track teams at the Wellesley High School. He is looking forward to another exciting year on the 420 race team!





 Ashley Quinn: Instructor in Training
 (Tampa, FL)

Ashley will be a sophomore at Plant High School in Tampa, Florida next year. Ashley has been sailing at SHYC since she was 7 years old and always loves to spend her summer sailing. In the past, she has won the Junior Seamanship award, Siewart cup, and various awards for Tuesday and Thursday Opti race series at SHYC. She has also raced in many regattas such as Stage Harbor, Chatham Yacht Club, and West Dennis regattas. Ashley cannot wait to be apart of the SHYC 420 race team and an instructor this summer!



 Maggie Forger: Instructor in Training

 (Norwell, MA)

Maggie will be a junior at Norwell High School, in Norwell, Massachusetts. Maggie has been sailing at Stage Harbor since she was 5 years old, and loves spending her time sailing in Chatham. In the past, she has won the Siewart Cup, and has raced in the Chatham, West Dennis, and SHYC Harbor regattas. This year, she has sailed on the Advanced 420 race team, took part in many regattas, and received all of the certifications necessary for being an instructor at the yacht club, and cannot wait for this upcoming summer!



 Ned Scudamore : Instructor in Training


Ned is 15 years old, is from England and goes to Cheltenham College in the south-west. Ned has summered in Cape Cod, Chatham, since he was two years old and has sailed at the club since Hermits. His club highlight was in 2017 when he won the Junior Hovey Cup and both August Tuesday and Thursday series in Optis. 




 Ryan Smith: Instructor in Training

 (Mendham, NJ)

Ryan is currently a sophomore at the Delbarton School in Morristown, New Jersey. In the past year, he volunteered for the club and participated in the Advanced 420 Race Team. In Ryan's years at the club, he has participated in regattas like the SHYC Opti Regatta and the Chatham Regatta, and was awarded the sailing school award back in 2014 and the sportsmanship award at the Chatham Regatta in 2015. This year, Ryan is finishing his required credentials to become an employee at the club over the summer, and he looks forward to it.


 Shep Hearle: Instructor-in-Training

 (Boston, MA)

Shep is excited to start working at SHYC after spending a year as a volunteer. He will be attending Phillips Academy Andover next year as a returning sophomore. Along with sailing, Shep likes to play football, squash, golf, and he also rows at Andover. Shep has won the Junior Hovey Cup, as well as getting third two years in a row for opti’s august Tuesday series. He cannot wait to get this summer started and meet the new kids that he will be teaching.





 Max Gryska: Head Steward

 (Marion, MA) 

Max is from Marion Massachusetts but has spent his summers in Chatham his whole life. Max graduated from his high school Tabor Academy this Spring (2019) and it will be his first year working at SHYC. He is very excited to be living in Chatham once again and to finally be working at the SHYC.



 Robby Driscoll: Head Steward

 (Lexington, MA) 

Recent graduate of Middlesex School in Concord.  He will be attending the University of Richmond in the fall.  He has  been sailing since he was five and has been involved with SHYC for his entire life.  He worked as a volunteer and an Instructor in training for SHYC before.  He became an Eagle Scout in the spring after the completion of his Eagle Project: the construction of a stage for the creche set of his local church.  Robby is incredibly excited to be on the staff  again, this time as a Steward, this summer!



 Website Services


Dawson Ritchie: Website Administration

 (Southborough, MA)

After serving as an Instructor and Steward over the past 4 years, I’m excited to remain a part of the staff and transition into Web Services. I’ll be working remote from Washington, D.C. where I’m at student at The George Washington University.






Marguax Angelino

Caroline Friendly

Catherine Walker

Sarah Leary