Ocean City Sailing Foundation
520 Bay Avenue - Bayside Center - Ocean City NJ 08226 ~ 609.418.3356
Robert DiMedio – Assistant Director - Robert lives in Haddonfield NJ and summers in Ocean City. He is a junior at The College of Charleston where he is studying finance. He started sailing at the Ocean City Yacht Club, starting with Optis, and eventually racing Lasers and 420s. This is going to be his third summer teaching sailing at the Ocean City Sailing Foundation. Rob is now a certified US Sailing Level One instructor.
Caleb Servis – Instructor - Instructor - Caleb is a senior at OCHS. I grew up near Ocean City, enjoy snowboarding and surfing whenever possible. I also have been rowing crew for 3 years at Ocean City HS. This is going to be his third summer teaching sailing at the Ocean City Sailing Foundation. Caleb is now a certified US Sailing Level One instructor.
Olivia Dunn - Instructor - Olivia grew up in Arlington, VA and spends her summers in Ocean City. For years as a camper and now an instructor, she enjoys sharing the fun of sailing with both kids and adults through the OC Sailing Foundation. Olivia
ran her own neighborhood summer camp during the two pandemic summers and volunteers with Special Olympics. Olivia is a rising high school junior and varsity member of both the girls rowing and track & field teams. She is a nationally ranked, 4x All-American javelin thrower and member of the State Champion girls rowing team at Wakefield High School.
Gavin Dunn – Instructor - Instructor - Gavin grew up coming to Ocean City every summer, and I fell in love with the OCSF through attending the morning classes. Now, I am an instructor teaching other youth the joys of sailing. As a Senior in Haddon Township HS, my extracurriculars include varsity rowing, wrestling, and swimming as well as cycling and weight training. I aspire to become a Naval Aviator after high school and attend college through a ROTC program.
Elena Buckwalter – Instructor - Elena Buckwalter is a Junior in high school. She summers in Ocean City and lives in Pennsylvania during the rest of the year. Elena started sailing on her family's 16 Hobie Catamaran. She then started attending OCSF summer sailing camps for six years.
Connor McGovern – Instructor - Connor is a senior at Haddon Township HS. He enjoys competitive rowing, rock climbing and sailing. After attending OCSF camps for several years, he is excited to now be an OCSF instructor teaching youth and adults the fun sport of sailing.
Tiffany Prettyman, Director
Tiffany Prettyman brings a lifelong passion for sailing, teaching, and coastal living
to her role as Sailing Director. Spending every summer and becoming a
permanent resident of Ocean City in 1995, she grew up exploring the back bays,
where her love for the water first took hold. Her boating journey began with a
Boston Whaler, and she learned how to sail on a GP-14, building a strong
foundation that would shape her future both on and off the water.
Tiffany’s connection to the Ocean City waterfront runs deep—she even met her
husband while working on the dock at 9th Street. Together, they raised their
daughters along the bay, instilling in them the same appreciation for sailing and
marine life that has defined Tiffany’s life. In fact, she taught her daughters to sail
before they could ride a bike, and they became active sailors at the Ocean City
Yacht Club, spending many summers competing in MAYRA races.
An experienced sailor and supportive mentor, Tiffany also spent time
assisting young sailors in coach boats and sailing a Lightning with her father at
the Ocean City Yacht Club—experiences that further enriched her understanding
of teamwork, racing strategy, and instruction.
Beyond the water, Tiffany is a dedicated high school world history teacher with 29
years of experience in education. Her dual passions for teaching and sailing
come together seamlessly, as she is committed to building confidence, skills, and
a love for learning in every sailor she works with.
Grace Mazzeo - Assistant Director - Grace grew up in Villanova PA and is a senior at The Episcopal Academy. Spending her summers at the Ocean City Yacht Club, Grace has sailed and raced Optis, 420s, and Lasers. She continues to travel with her Laser 4.7 to compete in MAYRA events as well as in the annual Junior Olympic Sailing Festival. Grace looks forward to her second year as an OCSF instructor and now Assistant Director.