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Captains Margie and Harold

Captain Margie and Captain Harold Ochstein have been married for 35 years and and own Island Dreamer Sailing School. They have spent the last 30 years exploring the Florida Keys in canoes, powerboats and sailboats. Both have USCG 100T Master's licenses with sail endorsements and are scuba divers. Harold is an American Sailing Association  certified sailing instructor and a certified rescue diver.  

In 1995, Margie and Harold purchased their first sailboat, a 25’ Venture, which was replaced several years later with a 27’ Catalina. After 6 years of weekend sailing in Biscayne Bay and the Florida Keys, with some month-long trips to the Bahamas, the time came to move aboard and cruise.

After cruising up and down the East Coast of the USA from New York to Florida, crossing to the Bahamas and spending more time in the Keys, they purchased a 37’ Irwin. Since then, the cruising continued throughout the Bahamas, the Southeast USA and the Keys; and eventually, the Irwin was replaced with a 41’ Morgan Out Island.     

During the last seven years, home base has been in Miami in the winter and the Florida Keys in the summer. Harold and Margie each captain there own 41’ Sailboat in the summer with the Boy Scout Eco-Adventure program and team up to teach couples in the winter. They have also worked together as Captain and Crew on the 83’ schooner “The Heritage of Miami II,”.  

Captain Margie

Captain Margie Ochstein was raised in the Panama Canal Zone. Her parents were from Terre Haute, Indiana, and her father was stationed in the Canal Zone during World War II. In high school, Margie was in Sea Exploring, a part of Boy Scouts of America, and earned her Coast Guard Auxiliary Basic Seamanship Certificate. After graduating from high school in the Canal Zone, she continued her education in Indianapolis, Indiana, graduating from Butler University. She and Harold were married and learned to Scuba dive together in Indiana before moving to South Florida.

After the move, Margie and Harold spent 12 years on the water in different sized power boats, diving and snorkeling all over Southeast Florida and the Keys. In 1995, they switched to sail boats and eventually were able to move aboard and to cruise. They travelled along the east coast of the USA and up the Hudson River to Albany, New York. Additional trips took them to Georgia, the Bahamas and the Keys.  

After returning to Miami and working as crew aboard the 83’ schooner “The Heritage of Miami II,” Margie followed Harold’s lead and also got her captain’s license. For the last three summers she has captained her own 41’ Sailboat at the Boy Scouts of America High Adventure Sea Base in the Florida Keys.

Captain Harold

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 getting married, both Harold and Margie learned to dive in Indiana’s limestone quarries. Since the diving is so much better in Florida, they 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 he chartering his own boat with the Boy Scouts, taking scouts for 6 days and 5 nights of snorkeling, fishing and sailing.