Captain Harold Ochstein grew up in the Midwest, where he began sailing on the local lakes when he was 10 years old. He graduated from Butler University in Indianapolis, Indiana with a Bachelor of Science in Business Administration. After learning to dive in Indiana’s limestone quarries, he and his wife moved south.
After settling in Florida, Harold began purchasing and working on a large variety of power boats and sailboats that he rebuilt, upgraded and then sold. He gained extensive experience on his power boats taking friends and family on sport drift-diving trips, snorkeling trips, and fishing and camping trips throughout Florida and the Keys. After purchasing his first sailboat in 1995, Harold began working and living on sailboats; and eventually, he earned his Captain’s license.
In his career as a Captain, Harold made many deliveries of new Catalina, Beneteau and Island Packet sailboats to the Miami Boat Show. He also captained a 36’ power cat operating as a commercial snorkel boat in the Keys. He ran the 83’ schooner “The Heritage of Miami II,” offering day trips from Downtown Miami into Biscayne Bay. He also captained “The Heritage” and “Yankee,” an 80’ schooner, both in the Boy Scouts of America High Adventure Sea Base program in the Keys for two years. He has spent the last four summers here chartering his own boat with the Boy Scouts, taking scouts for 6 days and 5 nights of snorkeling, fishing and sailing.