Our Faculty

Offshore Sailing School Faculty Managers and Instructors

From the day Steve Colgate opened his first school in Manhattan in 1964, he has insisted on sailing instructors with true 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 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


RANDON FINKELSTEINRandon-Finkelstein_465x700

U.S. Regional Manager

Florida and Other U.S. Regions

Randon is from Houston, Texas where he learned to sail at age 12 in the local lakes and the Gulf of Mexico. Being an avid sailor at age 16 he became certified in Keelboats and Cruising and holds US Sailing instructor certification through passage making. He currently holds his USCG 6 pack, RYA Yachtmaster Offshore, marine diesel engineering, and advanced open water diving licenses. He has sailed across the Atlantic from  Portugal to the Canary Islands and then to Antigua; and in Tahiti, Nova Scotia, The Florida Keys, Belize, Turks and Caicos, and The British Virgin Islands.

FOLKERT “DUTCH” JONGKIND(9a)_6.31_OurFaculty_FolkertJongkind_465x700

Caribbean Regional Manager

Caribbean & British Virgin Islands

Born and raised in the Netherlands, sailing was an obvious but casual hobby for Folkert. In 2006 he turned his hobby into a fulltime profession. He began teaching sailing on the Solent on England’s south coast, and seasonal work took him all over Europe and the Caribbean. He spent a year in the British Virgin Islands, then went back to the Solent to teach there for two more years; and in between did a lot of deliveries in the Bay of Biscay, English Channel and Atlantic Ocean. The BVI beckoned with sunshine, good wind, great people, and a great opportunity to work with Offshore Sailing School! Folkert holds Royal Yachting Association and US Sailing instructor certifications. Dutch began working for Offshore Sailing School as an instructor in 2014 and was promoted to Senior Instructor and Caribbean Regional Manager in the British Virgin Islands in May 2018.


Instructor Trainer and Manager

Captiva Island, Florida

Cheyenne Warner grew up on the island of Antigua where he started sailing when he was 3 years old. He learned on small boats at the local yacht club, and in his teens became a sailing instructor there. At 17 he was introduced to ocean racing, took Royal Yachting Association classes, and became a charter and delivery captain which led him to sailing all over the Caribbean, Europe and the United States. Cheyenne is a U.S. citizen and holds all levels of US Sailing Instructor Certification; as well as a variety of Royal Yachting Association and Maritime Training Certificates.


Fleet Maintenance TechnicianAndy-Ryner_199x300


Andy sailed for more than forty years on the great lakes, and has sailed in Florida since moving there in 2012. He has raced on various sailboats in a variety of races including several Port Huron to Mackinac Races and Chicago to Mackinac Races, as well as weekly sail club races. Andy has a degree in Mechanical Engineering and holds Marine Mechanic Certification.




British Virgin Islands

Originally a registered nurse Amanda  changed direction in life, combining her passion for sailing with a sailing career. She taught the RYA syllabus for over 10 years, and co-ran a sailing school out of Barcelona, then Gibraltar where she taught with a sea school there. Deciding a more dramatic change of location was in order Amanda left Gibraltar to join the Offshore Sailing School team in the British Virgin Islands in 2014 where she worked for Offshore for three years. She now lives in Great Britain and returns to the British Virgin Islands to teach on a seasonal basis.  Amanda has sailed across the Atlantic, around the Mediterranean, South East Asia, Australia, the UK and  the BVI’s. As an RYA Yachtmaster and US Sailing Cruising Instructor she is well practiced in both the RYA and US Sailing curricula. Amanda’s passion for sailing is well matched with her zest for life and travel. Amanda live in England and teaches part-time for Offshore on a seasonal basis in the British Virgin Islands.



British Virgin Islands

Rebecca was born and raised in Dublin, Ireland, where from a very early age she was adventurous and loved all sports, excelling in water sports. Late to the sailing scene, she stepped foot on a sailboat for the first time at twenty when she began to study Outdoor Adventure Management. Although holding a number of instructor-ships and leadership roles in varying water sports, she found that sailing and power boating were a clear favorite. After three years of study Rebecca graduated with an Irish Sailing Association certification as a Senior Dinghy and a Senior Powerboat instructor. She also achieved RYA Day Skipper Certification during her studies, and her goal was to keep improving and learning. She did this by sailing yachts around Ireland on both the Atlantic ocean and the Irish Sea, in all seasons with varying conditions, some worse then others. That experience was more than enough to achieve RYA Yachtmaster Offshore Certification in Ireland during the winter months, before joining Offshore Sailing School’s BVI team for some much deserved sun.



SW Florida

Kelly grew up in Texas and studied computer science in Colorado. He has taught live aboard courses extensively, sailed all over the Caribbean, Belize, Cozumel to San Pedro and the British Virgin Islands. For many years, Kelly raced Hobie Cats and ran a dive shop in the Florida Keys. He has a U.S. Coast Guard 50 ton license, US Sailing Basic Keelboat and Cruising instructor certifications, and is a PADI open water scuba instructor.



SW Florida

Originally from California, Richard has been sailing the waters of San Francisco Bay and the Pacific West Coast for over 25 years. He holds a U.S. Coast Guard 100 Ton Master’s Credential with sail and towing endorsements; and taught at the US Sailing school in San Francisco for over 10 years.  As an avid single handed sailor he has logged thousands of ocean miles from Mexico to British Columbia. In addition, he raced across the Pacific in the Pacific Cup race from SF to Hawaii and the Newport-Ensenada race in Southern California. He has done a number of delivery trips of sailing yachts from 42 to 65 feet – Mexico to California, Tahiti to Easter Island, and Fiji to Sydney Australia among others. In addition, he gained unique experience as volunteer crew on a 125′ top sail schooner travelling from the Great Lakes, into the St. Lawrence seaway to the North Atlantic and finally into the Chesapeake Bay. A photo of Richard is coming soon.



SW Florida

Steve joined Offshore Sailing School as an instructor in November 2014 after moving from California where he worked as a sailing instructor, charter boat captain, and manager of a Sailing School and charter company. He holds a USCG Master Captain 100 ton license and is a US Sailing certified instructor. Steve also worked as a Harbor Patrolman on Catalina Island and sailed Southern California waters for 40 years, living aboard his Beneteau 473 before moving to Florida.



British Virgin Islands

Patrick holds all levels of US Sailing instructor Certification: Basic Keelboat, Basic, Cruising, Bareboat Cruising, Coastal Passage Making, Performance Sailing Catamarans, Power Boats and Coastal Navigation and has a US Coast Guard Master 50 Ton license. Born in France, Patrick spent several years teaching sailing in Brittany, then in Los Angeles and Seattle. He has over 30 years of sailing experience, from small crafts to offshore cruising. teaches for Offshore Sailing School in the British Virgin Islands. 

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