OUR FACULTY

The Operations Team — Offshore Sailing School Managers and Instructors

Offshore Sailing School instructors are US Sailing certified to teach beginner through advanced passage making sailing courses. Those who teach power cruise courses hold US Sailing and US Powerboat instructor certifications too. From the day Steve Colgate opened his first school in Manhattan in 1964, he has insisted on sailing instructors with excellent teaching skills, keen sailing knowledge and extensive sailing experience in small and large cruising and racing boats. Offshore Sailing School instructors are men and women chosen for all of the above, plus humility, patience, dedication to you (our clients) and loyalty to Offshore Sailing School (the company). Here are some of the special people that deliver “exceeded my expectations” comments on almost every evaluation we receive back from our clients. If you would like to join our faculty, please see Employment Opportunities.

“Instructors I have encountered in the sailing world have been very good, but those with the Offshore Sailing School have been the best. The curriculum development with Offshore advances their instructors to the highest level. The Offshore instructors are following a well thought-out script.”

John Klebba
Lakewood, CO

INSTRUCTORS

Captain Andy Deen

Instructor

Captain Andy Deen is a Tampa native and will use his knowledge of the local waters to make your charter a relaxing and memorable experience. Andy holds the USCG 100-Ton Masters license with sailing endorsement and is also an American Sailing Association (ASA) Instructor of the year for 2022 and 2023. If your party includes children, Andy will use his experience as a former high school teacher to help accommodate groups with mixed ages. If you are itching to cruise beyond the Bay, he is familiar with the Florida Gulf Coast and will suggest an exciting multi-day itinerary. Welcome aboard!

Vanessa Goodrum

Instructor

Captain Vanessa brings recognized instructional certification plus 11 years of live-aboard experience, including a 9-month voyage from St. Petersburg to Boston. Living aboard her sailboat, she mastered boat systems and self-reliance skills. Her instruction spans luxury Bahamas catamarans to diverse coastal waters, covering both monohull and multihull dynamics. Vanessa teaches practical skills through real-world scenarios, specializing in coastal passage planning, anchoring, boat systems maintenance, and weather routing. Students gain technical competence plus the sailor's mindset from her extensive cruising experience, developing judgment, confidence, and sea sense for safe adventures. She keeps instruction engaging and fun while building real skills.

Wayne Cook

Instructor

Captain Wayne grew up in south Louisiana and started sailing at the young age of 10. He was introduced to sailing by his uncle who raced on Lake Pontchartrain in New Orleans. After many years of sailing, he and his wife Carrie took formal sailing lessons. It wasn’t until he retired from the corporate life in Dallas that he started his next passion, teaching sailing. With no hesitation, he and Carrie moved to Saint Petersburg, Fl to continue his love of instructing and their love of sailing. They have taken numerous charters to the British Virgin Islands, not only to teach and captain, but for pleasure also. Captain Wayne believes in the hands on teaching method. In other words, he will show you how to do it, then let you do it until you can master it. Being instructed by Captain Wayne is always fun and relaxing, that is why he has so many returning students.