Island Caretaker
Osprey
East Hampton, New York
Embark on your next adventure. Join our team as an Island Caretaker!
Currently recruiting for the season from November 2nd, 2026 to March 1st, 2027.
We are a family dedicated to preserving and stewarding a ~3,000-acre island off the coast of Long Island, New York. The island is rich in historical significance and has been in the family for hundreds of years. Most importantly, it is an extraordinary wildlife sanctuary. Our goal is to continue to preserve and maintain the island for many future generations.
The property features diverse landscapes including forests, fields, shoreline, and protected wildlife habitat. Rich in history and natural beauty, the island offers a rare opportunity to experience a remote coastal environment that can only be accessed by private boat. Its secluded setting provides unmatched scenery, tranquility, and direct access to nature.
East Hampton, New York
Embark on your next adventure. Join our team as an Island Caretaker!
Since 1995, CoolWorks has connected adventure-seekers with job opportunities in amazing places—from national parks to ski resorts, summer camps to dude ranches. We help people trade screen time for real time—meaningful experiences that spark connection and growth. Your next great adventure is waiting. More About CoolWorks