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Couples Sailing School
Island Dreamer
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Here Are a Few of Our Captains

Our supportive approach allows each of you to build your skills and confidence at your own pace and to share in the decision making process, making sailing comfortable for everyone.

Join Us And Step Aboard The Cruising Lifestyle

Captains Margie and Harold Ochstein -  Harold and Margie Ochstein have been sailing and boating in the Florida Keys since 1983 and look forward to sharing their knowledge of this beautiful island chain with you. For the last 7 years they have been chartering and teaching sailing in the area, helping couples learn the joys of sailing together. They also have interesting experiences to share about living aboard a sailboat, sailing with the Boy Scouts and travel to places such as Panama, Greece, Israel. They have cruised the East Coast of the US and the Bahamas extensively and have captained boats as large as an 84' schooner. Both have USCG 100T Master's licenses. They own Island Dreamer Sailing School in Miami. Harold is an American Sailing Association certified sailing instructor and a certified rescue diver.

Captains Ann Brainard and Bob Kruk each have over thirty years of sailing experience on unsalted and salted waters.  Living aboard their 42' Catalina Selah, they offer charters in the Keys, the Great Lakes, and Greece. Bob and Ann have transitioned from mainstream business careers to the sailing lifestyle – allowing them to connect with nature and inspire people in positive ways. It’s about freedom, harmony, and purpose.  Our hope is that people leave inspired.  It’s not just about the sail, it’s about being a force for good. With a “Couple” of Captains on the boat we offer personalized male and female perspectives on sailing. They own Couples Sailing School.

Captain Louise Orion has sailed over 50,000 miles and truly enjoys both offshore sailing and cruising. With a First Mate, she currently teaches beginning and advanced cruising strategies to couples, while cruising the Caribbean full time on her Hylas 47’ Blue Planet.

Captain Orion holds a 200 ton Master of Yachts Ocean ticket from the UK, She also has an 100 ton USCG license . She  is one of the few  ASA Instructors certified to teeach ASA 108 Offshore Passagemaking. She has an an unflappable cheery disposition along with the knowledge to help you acheive your cruising goals.

Captains Derrek Polt and Stephanie  Mansberger -They  live aboard  a 41’ Morgan Out Island and teaching ASA classes  in Miami and the Keys, Derrek has been sailing since the age of twelve on boats ranging from small sunfish to 75’ schooners. He grew up in Minneapolis, MN. He sailed the Schooner Yankee, a 75’ schooner and Calypso Gypsy, an 80’ sailing yacht, and was Captain aboard Pirates Choice, a 45’ gaff rigged ketch. Derrek is a USCG licensed captain and an ASA instructor. Stephanie started learning  sailing, navigation and seamanship at the age of thirteen with the Sea Scouts.  She has experience in the Florida Keys, on Lake Erie, in the Chesapeake Bay, and in the British Virgin Islands. She grew up in Morgantown, WV mostly sailing on small lakes and rivers.  Stephanie has worked at the BSA’s High Adventure Seabase in the Florida Keys as their Sailing Commissioner.  Stephanie is a USCG licensed captain and a ASA certified instructor.

Captains Jean Levine and Jeff Grossman Jeff grew up sailing in the Florida Keys and the Bahamas and learned to visually pick through reefs before learning to drive a car. Jeff has been actively sailing over 45 years and as captain since the age of 15. Jean Levine has been sailing since she was 12 years old first on the Chesapeake Bay and then in the Caribbean on vessels ranging from sunfish to 80’ schooners. Jeff and Jean have extensively cruised the Caribbean and Florida on their current boat a Skye 51. Jeff holds an Electrical Engineering degree and worked with almost all forms of electronic navigation from B-52 Inertial Navigation systems to modern integrated ARPA radars. Jean is an Accredited Marine Surveyor, a member of the Society of Accredited Marine Surveyors (SAMS) and is ABYC Standards Certified. Both Jeff and Jean are 100GT Masters and ASA Certified Sailing Instructors. Jeff and Jean assist couples in realizing their sailing dreams.      

Captain Scott and Gail Penfield - Scott was raised in Cleveland Ohio, learning how to sail on his father’s sailboats and through the yacht club the family belonged to.   He raced his father’s Rhodes 18 in his early teen years and in later teen years crewed on various “big” boats until joining the Air Force in 1969.  He and his wife Gail moved to Florida in 1972, and raised two sons.  Once the boys graduated from college, got married and moved on they purchased their dream boat a CSY 44 walkover “Chanticleer”.  For the last 11 years they have completely rebuilt and restored the boat to its current condition and have sailed over 18,000 miles up and down the East Coast and the Bahamas.  Five years ago Scott obtained his Coast Guard Captains license and started doing charters for the Boy Scout High Adventure Florida Sea Base. He is an ASA certified instructor and along with Gail can show you what cruising and living aboard is really like.