Nathaniel Osborn



2025-26 Sailing Head Coach

2024-25 Sailing Head Coach


Nat Osborn – Sailing Coach & Program Coordinator

Since 2013, Nathaniel “Nat” Osborn has been a cornerstone of The Pine School’s sailing program, serving as both coach and coordinator. A native of Santa Barbara, California, Nat brings a lifetime of experience on the water, with an impressive background in both dinghy and offshore racing.

Nat’s passion for developing sailors is matched by his dedication to teaching. He began coaching in 2002 at the US Sailing Center Martin County and continues to instruct youth and adults there today. His patient, knowledgeable approach inspires confidence in beginners and challenges experienced sailors to push their limits, creating a team culture built on skill, sportsmanship, and love for the sport.

Whether coaching in regattas or instructing at the dock, Nat’s commitment to his athletes and the sport of sailing has helped The Pine School’s program thrive for over a decade.