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.





St. Petersburg, Florida

Hunter joined the Offshore Sailing School team in late 2017 when he sailed his Catalina 470 to Florida from Long Island, New York. He is a US sailing certified instructor, and has been a USCG licensed captain for over 14 years. For more than 30 years Hunter sailed up and down the east coast from the islands to Maine, made numerous deliveries from the Caribbean, Bermuda and Chesapeake logging over 20,000 miles over the years. He has owned sailboats since 1984 when he bought the 19’ Cape Dory Typhoon and currently lives aboard his Catalina 470. Hunter served in the US Navy as a operating engineer with two tours in the Middle East, South America, Europe and Africa, and first sailed while stationed in Charleston, SC where he raced Hobie Cats. When discharged from the Navy, Hunter returned to New York and  became a Master Plumber, running his family business for over 38 years. As a mechanic by trade he maintains his own boat while helping others. Hunter is now dedicated to living and teaching his true passion, sailing.



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. 



SW Florida

Clint hails from the northern California coast. He started sailing with family and friends on home built boats, Snarks, and Hobie Cats at the tender age of two. As he grew, so did his passion. His father’s move to Florida’s Gulf Coast afforded him the ability to experience larger yachts and open water, during his visits. When he was a junior in High School, he joined the Sea Scouts and over time, rose from crew to junior officer, then officer, while serving on the Compass Rose in San Francisco Bay. As an officer, he mentored and trained younger recruits in all aspects of seamanship. For his high school senior project, Clint built his first sailing pram. After college, he added to his knowledge of boat building, repairs, and mechanics by working for several yacht builders and boatyards. In 2009, Clint became a licensed captain and soon began running commercial sailing craft on Florida’s nature coast. These days, the married father of three lives in Gulfport, Florida and enjoys teaching for Offshore Sailing School. When he isn’t sharing his love of sailing with his students, you might catch him giving salsa lessons!




SW Florida

A Florida native, Brian has been a member of the Offshore Sailing School team since 2005. He started racing dinghies at 11 and has enjoyed sailing and power boating in Southwest Florida ever since. Brian graduated from the University of Florida, is a licensed U.S. Coast Guard Captain and certified US Sailing instructor. He teaches all Offshore Sailing School courses – from Learn to Sail, Performance Sailing and Racing, to cruising and passage making courses on monohulls and catamarans. He was manager of Captiva Island and Ft. Myers Beach, Florida campuses prior to moving to the British Virgin Islands, where he managed our Caribbean locations for four years. Brian is back in Florida as a full-time resident.

JEFF WERNER(12a)_6.31_OurFaculty_JeffWerner_465x700



Key West’s warm weather and sailing lured Jeff from the Midwest where he learned to sail at the University of Michigan. In 1992 he got his U.S. Coast Guard Master’s license, and followed Caribbean breezes to St. Lucia to manage Offshore’s Windward Islands campus. Jeff has done two Atlantic crossings under sail and worked professionally throughout the Western Mediterranean, Caribbean, Bahamas, and Eastern Seaboard, Gulf of Mexico and Great Lakes, operating private and charter motor and sailing yachts. Jeff holds US Sailing instructor certification and is Offshore’s lead celestial navigation instructor.

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