The Operations Team — Offshore Sailing School 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 ManagerRandon 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.
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 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.
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.
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 was born and raised in the warm tradewinds of Puerto Rico and has spent over 50 years sailing all over the World on everything from windsurfers to maxi yachts. His dad started him as crew on a C&C 41 in the early 70’s. When he was just 12 years old, Jaime did his first delivery from Annapolis to San Juan, PR. Since then, he says he has never stopped sailing in one form or another and has rarely been more than a few minutes from the water. “Sailing is my greatest passion,” says Jaime. “I spend every free second racing RC boats, wingfoiling, or organizing racing in my sweet Melges 24 in the local fleet or around the US.” Jaime gets immense satisfaction from improving people’s recreational and racing experiences in St. Petersburg, Florida. “I love my work as a sailing instructor, delivery, and charter captain, but one of my favorite jobs is serving as the Race Manager for Antigua Sailing Week. It brings me back to the Caribbean every year, where I reconnect with my sailing roots.”
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 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.
Elin has lived and sailed all over the world, and is enjoying a change from the frigid North Atlantic and Irish Sea to the much warmer waters of the British Virgin Islands. She is an RYA Yachtmaster and loves sharing her passion for sailing on boats large and small. Coaching and mentoring female sailors and skippers is particularly important to her, as well as making a vacation, life or career on the water accessible to everyone. When she’s not teaching sailing, Elin can be found offshore racing or on long ocean passages while trying to perfect her celestial navigation.
Daniel is originally from England, but he found his love for sailing when he moved to the Pacific Northwest in 2011. He and his wife Klaudia have owned several cruising sailboats and have explored the expansive waters around Seattle and Puget Sound for the last decade. Daniel is also an avid racer. He sailed for his local club in Olympia, WA during the last 6 years while delivering yachts up and down the west coast in his spare time. Daniel has held a USCG OUPV (6 pack) license for the past 5 years and recently upgraded to a 25-ton Masters License. Daniel relocated to Florida full time where his passion for sailing and teaching continues. He looks forward to exploring the waters and assisting you in reaching your own sailing goals, whether that’s learning how to sail, owning, or chartering a sailboat or just having a great time out on the water.
Mark Walker is a seasoned US Sailing Instructor with over a decade of experience sailing across the Caribbean and Gulf Coast waters. He has done multiple deliveries through Caribbean waters, enhancing both his sailing expertise and appreciation for the region’s unique challenges. An advocate for marine conservation, Mark emphasizes the importance of preserving ocean ecosystems in his teaching, focusing on creating a supportive and empowering learning environment for sailors of all skill levels. Eager to share his passion for sailing, Mark looks forward to embarking on new adventures with students, aiming to create lasting memories while fostering responsible maritime practices. His versatility as an instructor makes him an invaluable asset to Offshore Sailing School and a trusted guide for both novice and seasoned sailors.
Trevor is a 7th generation Floridian who has been on boats since before he could walk. He began sailing with his father when he was five and has put in his fair share of time on the water – from sailing the tropical waters of the Caribbean to the cold, icy waters of the Greenland fjords. Trevor loves sharing his knowledge with everyone he encounters, especially as an instructor for Offshore Sailing School. He believes in putting extra emphasis on self-sufficiency on the water so you can be prepared for anything when you are out in the ocean away from the nearest boatyard. When not working professionally with Offshore Sailing School, Trevor spends his free time fixing up and cruising on his own sailboat in the Tampa Bay area and beyond, and invites those who want to learn sailing and cruising to join him for a relaxing and informative week on Florida’s beautiful coastline.
Dave brings over forty years of knowledge on marine and commercial equipment and systems as our Fleet Maintenance Manager. His background includes service in the USMC and the USCG, retiring with over twenty-three years of service from USCGR as Machinery Technician Chief Petty Officer. He utilizes his diverse background and experience to ensure our vessels are kept in tip top shape. Interesting trivia on Dave, he is our Square-Rigged Sailor, having sailed on the USCG Cutter Barque Eagle (America’s Tall Ship) in 2001 as a crew member and instructor on engineering and damage control to Officer Cadets from the USCG Academy in New London, CT. When not working he is an avid outdoorsman and can be found in the woods or on the water.
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.
More bios and photos to come . . .