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 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



Randon Finkelstein – US Regional Manager

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. He is a member of the prestigious US Sailing National Faculty and a certified US Sailing Keelboat and Cruising instructor in all levels from Basic Keelboat through Passage Making. He also holds several other licenses and certifications including: a USCG 6 pack , RYA Yachtmaster Offshore, marine diesel engineering, and advanced open water diving. 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.


Dutch Jongkind – Caribbean Regional Manager

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.


Cheyenne Warner – Instructor Trainer

Instructor Trainer

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.


George Samalot – Instructor


While working at Ulmer Sails on City island, NY in 1976, George taught part-time at Offshore Sailing School on City Island. That Fall he joined Offshore full time at South Seas Plantation on Captiva Island, Florida, a year later went back to Offshore on City Island NY and then to the British Virgin Islands to open an Offshore Sailing School branch there. After a long career delivering yachts, sailmaking, and running his own company Samalot Marine for 35 years, George and his wife, Barbara, moved to SW Florida where he joined Offshore Sailing School to teach sailing, again. An avid racer, he has sailed multiple times in the Newport-Bermuda Race, the Southern Ocean Racing Circuit, many distance races on Long Island Sound, was on the US Admirals Cup Team in the 1987 Fastnet Race and did the Miami-Montego Bay Race in ‘89. A racing association leader and volunteer, George received the Ned Anderson Trophy from YRALIS for “Outstanding Service to Yacht Racing” on Long Island Sound in 2012. He holds a US Coast Guard 200-ton Masters License with sailing endorsement and US Sailing instructor certifications.


Andrew Deen – Instructor

Andy Deen – Instructor


Andy’s love of naval history ultimately led him to try sailing lessons, and he was hooked! He and his wife Kathryn joined a sailing club and have cruised up and down the west coast of Florida, as well as throughout the Virgin Islands. Andy loves sailing so much that he decided to change careers and teach sailing full-time. He holds the USCG 25-Ton Masters license with sailing endorsement. Andy is excited to share his passion with you and hopes that you depart from the course with a newfound confidence to charter a sailboat, anywhere in the world! Welcome Aboard!


Jaime Torres – Instructor

Jaime Torres – Instructor


Jaime was born and raised in the warm tradewinds of Puerto Rico and have spent well over 50 years sailing all over the World on everything from windsurfers to maxi yachts. Sailing is my greatest passion, and improving people’s recreational and racing experiences is what I live for. I currently reside in St. Petersburg, Florida, and work as a sailing instructor, delivery and charter captain, and Race Manager of Antigua Sailing Week.


Rebecca Brannigan – Instructor


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.


Kelly Davis – Instructor


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.


Patrick Najou – Instructor

Patrick Najou – Instructor


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. 


Andy Ryner – Florida Fleet Maintenance Technician

Andy Ryner – Fleet Maintenance Technician

Florida Fleet Maintenance Technician

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.


Andrew Sumpton – Instructor

Andrew Sumpton – Instructor


Mark Walker – Instructor



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