In Annapolis, if you cross Spa Creek in the summertime, you’ll see them: small figures in multicolor lifejackets, moving, at various speeds, rigging bathtub-like boats. These summer camp sailors are setting out on what will, for some of them, develop into a year-round and perhaps decades-long pursuit.
The junior sailing experience: fun and life lessons
In the Annapolis area, the Annapolis Yacht Club’s (AYC) junior sailing program is the launch point for many of these youth sailors. The program’s director, Robert Lippincott, wants to maximize the fun and life lessons these junior sailors experience. Lippincott looks to take “what sailing’s done for me, and to make it even better…to provide a Walt-Disney-World-like experience for the next generation of sailors.”
Lippincott’s sailing started on the other side of the Bay, where he grew up in Oxford, MD, spending a large part of many days “sailing on the waters of the Tred Avon River (TAYC).” He comes from the Lippincott boat-building family, originally from Riverton, NJ, who constructed Stars, Comets, Lightnings, Snipes, and many other classes. Lippincott formally started at TAYC at age eight and moved through intro racing to TAYC’s Green Fleet and Red, White, and Blue teams. Thanks to the late sailing director Diana Mautz, he sailed under coaches hired from other countries, including Maiken Kold from Denmark. Lippincott noted that sailing under coaches with non-American accents at different times in his career forced him to pay better attention to details and work harder on the water, and that he now seeks out foreign coaches for his sailors.
As an Opti sailor, he qualified for the Chesapeake Bay Optimist Team (CBOT). At that time CBOT was one of a few teams that “would travel all over the country,” Lippincott said, and “were very strong in the early ages before yacht club race teams existed.” His time on CBOT helped him learn independence, as he would travel between Norfolk, Hampton, the Eastern Shore, Gibson Island, and Annapolis to practice. He mentioned coaches Juan Carlos Romero and Molly and John Vandemoer as important influences.
Lippincott sailed youth 420s at both AYC and Severn Sailing Association (SSA), while attending Christchurch School on the Rappahannock, and later Salve Regina University in Newport, RI. He started sailing the Star boat at age 18—a class that holds much history for his family, and in which he still competes. Lippincott began coaching at Fishing Bay Yacht Club in 2008. He coached Optis there and at TAYC, as well as high school sailing at SSA and Christchurch. In 2017, he accepted the “opportunity of a lifetime” spot as the Optimist Program Manager and head RWB coach at AYC. This happened to be the same year that my younger sister started sailing Optis under “Coach Bobby” at AYC, and she will start college sailing in the fall, along with several peers who started in Optis under his tutelage.
Cultivating his sailors’ love for the sport and Corinthian spirit.
In 2021, Lippincott rose to director of Junior Sailing, taking on the task of managing one of the largest junior programs in the country. “I consider myself to be coaching coaches now,” he said. Participation continues to grow; there are currently 482 sailors in the summer program and approximately 716 junior sailors in the calendar year.
Lippincott said his goal as a coach and manager is to help people “find what their passion is and to love it and really devote themselves to it.” He emphasized the importance of “a fighting spirit” and refusal to quit for success in racing. “There’s going to be really tough days… but they have to understand they have their whole life to do it.”
As director, Lippincott often has to manage parents’ expectations, and he emphasizes that with dedication and love for sailing, success will eventually follow. The coach’s dedication to cultivating his sailors’ love for the sport and Corinthian spirit showed when he was nominated for and named as the Sail One Design Coach of the Year in 2021.
I asked Lippincott about his goals for AYC’s junior program. In upcoming years he wants to host “red-carpet, world-class” events and high-caliber junior regattas. These include fun clinics allowing for “learning opportunities for people that might not be able to do a full season.” He’s focused on providing the little things, like cool regatta swag and more affordable events, that will improve kids’ experience.
In 2025, AYC added a junior Snipe class thanks to two boats given by an anonymous donor. AYC sailors competed in their first Snipe regatta this June. The club also hosted a WASZP clinic this spring, and Lippincott says he hopes to introduce more classes, like keelboat sailing or wing foiling, that will keep young sailors on the water even as they move on to college. He said he’d be willing to consider restarting the Laser program someday if there was more area demand than SSA could meet.
With all the logistics that come with providing these opportunities, Lippincott’s childhood at the marina serves him well. He’s been moving travel lifts and trailers from a young age and has experience navigating yacht clubs AYC travels to up and down the coast.
Lippincott says he always tries “to put the kids first” before his own sailing, but he does get out “in the off-seasons when time allows it,” usually the winter months. His favorite thing to do is to sail a Star boat out of Miami, and he does Star regattas over the summer, including Star Worlds when it’s in the US.
By Storrie Kulynych-Irvin
