LA SPERANZA

Captain Sean O'Grady
Captain Sean discovered a love for the ocean at an early age while sailing with his father, setting the course for a lifelong connection to the sea. After a brief time away from the water, he returned to sailing in the San Francisco Bay, where he quickly immersed himself in both racing and charter work.

Since 2018, he has worked with USA76, a former America’s Cup IACC yacht, gaining invaluable experience aboard one of the sport’s most iconic vessels. His maritime background also includes commercial fishing in Alaska, sport fish guiding, and time aboard large private yachts. He later served as both Maintenance Director and Captain for a pair of Santa Cruz 70s in Monterey Bay, where he spent two years overseeing operations and delivering unforgettable sailing experiences.

Now based in the Caribbean, Captain Sean brings his expertise, enthusiasm, and easygoing nature to every charter. He holds a 100 Ton Near Coastal Master License with STCW, Sail, and Assistance Towing endorsements, and places the highest priority on safety, service, and guest enjoyment. His philosophy as a captain is simple: create a fun, relaxed atmosphere where everyone can laugh, connect, and fully embrace the beauty and adventure of island life.