Hudson River Community Sailing develops leadership and academic success in underserved New York City youth through sailing education and provides maritime education and recreation to the community at large. Hudson River Community Sailing (HRCS) was founded in 2008 to teach math, science, and leadership to NYC public school students through sailing. When it was founded, the program served 30 students from one high school and was a semester long. We now serve 225 students from thirteen schools over the course of an academic year through Sail Academy. On an average day, a student in Sail Academy might learn to calculate the speed of the river current, study the ecology of the Hudson, or practice the fundamentals of sailboat racing. After their first year, students may apply for internships, where they work intensively in a particular department at HRCS. We operate Sail Academy in the context of a vibrant Community Sailing center that gives New York City affordable access to the water. The Community Sailing program also provides meaningful internships. This relationship ties together the two sides of our work. As Sail Academy in Chelsea reached capacity, we decided to build a program based on the same principals, to serve younger students in a new, higher-needs neighborhood. In the fall of 2018, we launched a second Sail Academy for middle school students in Inwood. In the summer of 2021, HRCS launched an Adaptive Sailing program to serve youth and adults with a range of physical and developmental disabilities. We partnered with five groups in our first year, and plan to use the findings from the pilot program to make necessary adjustments.