The Sapling program is Oakcliff Sailing’s offering for sailors who are considering sailing as a career. In the summer long program, Oakcliff Sailing trains the sailors in all of the skills they need to succeed in professional sailboat racing.


2019 Saplings


2018 Acorn, 2019 Sapling
Brian started sailing at the age of three but never enjoyed it. It was only when he competed in the 2017 Around Long Island Race that he caught the offshore bug. His sole focus is on offshore racing and his Read More
Shorthanded Offshore Sapling
Hometown: Hyannis, MA, USA. My name is Matt Hersey, I grew up racing Optis, C420s and Lasers on Cape Cod, occasionally racing PHRF and extensively team racing with Barnstable High School. I plan to continue coaching at Hyannis Yacht Club Read More
Purchasing Manager, 2019 Sapling
Hometown: Reno, NV, USA. Hello! I’m Calicima I go by Cali. I grew up sailing on Lake Tahoe in my family boat until I was about thirteen years old. I started sailing again around seventeen in San Francisco bay on Read More
2019 Sapling
Hometown: Oyster Bay, NY, USA. I started sailing in Oyster Bay on classic yachts and went on to captain my high school dinghy team, manage a local sailing school, and compete at the collegiate level. I'm currently studying aerospace engineering Read More
2019 Sapling
Cedric Keneipp, otherwise known as Wes grew up in Bellingham WA, just north of Seattle. He started sailing on the high school team five years ago and never missed another opportunity to be on the water since then. Starting with Read More
2019 Sapling
As a multi-sport athlete, I have had the opportunity to face a number of challenges and find that my process for reaching success is transferable. As a sailor, I live for the moments when I am challenged, yet triumph through Read More
2019 Sapling
Makalynne grew up sailing scows at summer camp in Minnesota. After falling in love with sailing and wanting to develop her skills, she started sailing in her home state of Colorado. With sailing being a scarce sport In Colorado she Read More
2019 Sapling
My name is Dylan Saxman. I started sailing at 8 where I found my passion for the sport. Throughout my short sailing career I have tried to spread myself out and try sailing in as many classes as I can. Read More
2019 Sapling
Connor grew up sailing in Lake Forest, Illinois, starting in Optimists, and sailing Lasers and Club 420s. He is currently a student at Tufts University, and a member of the sailing team. Currently, he is focused on match racing, inshore Read More
2019 Sapling
Kirby grew up in North Carolina on his family's farm. He is a rising sophomore at The University of Virginia. Although he did not grow up sailing regularly, he acquired a love of the sport during vacations to the Bahamas. Read More
2019 Sapling
My name is Sam Rifkind-Brown. I am 16 years old and a rising junior at Georgetown Day School in Washington, DC. I grew up sailing over the summer and started racing for my high school a couple of years ago. Read More
Fran is an officer of the Germany Navy from Hamburg. She is currently working on her master’s degree in educational sciences at the Helmut-Schmidt-Universität, university of the armed forces in Germany. Her prior sailing experiences include basic sailing within the Read More