SCOTT DEMPSTER, Founder, Virgin Island Sailing School
Captain Scott learned to sail as a teenager and spent most of his time cruising and racing up and down the coast of California and Mexico. He made his first trip to the USVIs in 2005, and quickly recognized it as a place where he could combine 3 of his biggest passions: sailing, teaching and tropical islands. Soon after, ascribing to Mark Twain’s philosophy that you will always regret what you don’t do far more than what you do, he began captaining charters and teaching sailing in the islands. Realizing the need for an ASA certified school there, and drawing upon his stateside successes as a business owner and entrepreneur, he founded Virgin Island Sailing School in 2010.
Scott holds a USCG 50-ton captains license with several endorsements, including auxiliary sailing. He is a certified American Sailing Association (ASA) instructor in levels 101, 103, 104, 105 and 114, a passionate and accomplished yacht racer, and a not-half-bad surfer and musician.
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DON and LINDA ALLEBACH
Simply put, I am passionate about sailing. In fact, I love almost anything to do with being on the water. I’ve been sailing ever since I was a kid with my dad on small inland lakes. Once I got married and had kids, my sailing evolved to a new level. Like many other sailors, we became competitive.
My wife and I have become avid C-scow racers. We spend a good part of the summer traveling from regatta to regatta on inland lakes around the Midwest. Racing is addictive and it forces you to keep pushing the edge to try new things that improve your skills. About 10 years ago, I got my OUPV (6 Pack) license and over time I upgraded it to a Masters 50T. Since then, we’ve been taking out private charter tours throughout the Caribbean islands, places like BVI, Grenada, Belize and St Lucia.
Almost all of my experience has included my wife Linda (married 50 years). We’ve even chartered boats further north like the Great Lakes, Nova Scotia, and San Juan Islands in Washington State.
Now that I’ve retired from my engineering job, I can share my love of sailing with anyone who wants to learn. For the last few years, I’ve enjoyed being seasonally employed as a captain of a 44’ ketch at the Biscayne National Park Institute in the Biscayne National Park in Florida. We sail out to the Keys with a boat full of visitors exploring the mangrove lagoons in the national park. We introduce our visitors on paddleboards to discover sharks, stingrays, crabs, pelicans and all kinds of wildlife. In addition, in my spare time I am the Director of the Quad City Sailing School in Davenport, Iowa.
Teaching sailing in the Virgin Islands is a wonderful place to share my passion with others. There are few things more satisfying than watching new sailors gain experience and confidence at the helm. Imagine the end of a great day learning to sail, anchor down in a quiet bay, cold drink in hand, dinner on the grill, watching the sunset. It doesn’t get any better!
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JT QUINN
Captain JT first started sailing while living in New Zealand. He has spent time working on yachts all along the Atlantic Coast, Caribbean, and the Med. He has crossed oceans, sailed to every island in the Caribbean, and transited the Panama Canal. Whether it’s long, open water passages or cruising the islands, JT loves to share his stories and knowledge about sailing.
JT holds a USCG license, RYA Yachtmaster, and is a certified ASA instructor.
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TIM OVERDORF
Whether it is racing sailboats on the Great Lakes, cruising through the Mediterranean and Caribbean or even sailing in open blue water with no land in sight for hundreds of miles – Captain Tim has a passion for sailing! Tim wants to share his passion for sailing with as many people as possible which lead him to become an ASA sailing instructor. His philosophy is that your lessons should feel like a learning vacation – the first order of business is of course learning how to sail, but not too far behind that – you need to have fun while learning. After all, how can you develop a passion for anything if you aren’t having fun while doing it. With his patient teaching style, extensive knowledge of all the anchorages in the Virgin Islands and long list of sailing stories to tell, Captain Tim will make sure you learn to sail, can handle being skipper of your own boat and most importantly have fun while learning!
Captain Tim is certified to teach ASA courses 101, 103, 104, 105, 106 and 114. He holds a USCG Master Captain License 25T with sailing and towing endorsements.
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AMY GALLAGHER
Captain Amy believes that it’s never too late to learn to sail. She learned as an adult and bought her first boat, a Beneteau First 310 Tall Rig, the same summer. From her base on Lake Michigan, she began local and long-distance racing, most notably as crew on, “The Hook”, an annual 189-nautical mile race. Quickly building her sailing skills and confidence, it wasn’t long before she embarked on month-long sailing adventures, roaming across Lake Michigan, Lake Huron, and Lake Superior with complete beginners as crew.
It was during these sails that Amy realized she could combine her previous teaching experience with sailing. Amy loved helping her crew feel more confident on the water, especially during those challenging moments that are always a part of sailing. Her teaching style is fun and safety-focused and she is committed to creating a low-stress learning environment.
Captain Amy has over 400 days of sailing experience in the Atlantic, the Caribbean and on the Great Lakes and holds a US Coast Guard OUPV license and is certified to instruct ASA classes: 101, 103, 104, 114, and 116.
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JIM & BONNIE STOLL
Captains Jim and Bonnie Stoll began their sailing education in 2007 aboard a Beneteau 43 in the BVI with their two daughters. During that charter the whole family not only learned to sail but learned to function as a crew. Jim earned his ASA 101/103/104 at that time while everyone enjoyed the beauty and excitement of the Virgin Islands. Upon returning home, they joined SailTime Chicago and continued to gain sailing experience on Lake Michigan. After moving to Florida, they purchased their first boat, a Jeanneau 379 (SV Anchored in Hope) and sailed her around Florida for seven years.
Jim and Bonnie both retired from their previous careers in 2020 and now work together as boat captains. They truly enjoy teaching couples and families to sail together. They also work as delivery captains moving boats for owners as well as providing training to them as they get to know their new boats. In 2023 Jim and Bonnie moved up to a Lagoon 42 catamaran and are now living aboard and cruising the beautiful islands of the Caribbean. Bonnie has always dreamed of owning a Bed & Breakfast – Can you think one with a better view?!
Jim is a retired United Airlines pilot who loves teaching and holds a USCG Merchant Mariner OUPV and 25 Ton Masters credential, as well as ASA instructor certifications for teaching ASA 101 / 102 / 103 / 104 / 105 / 106 and 114. Bonnie had a diverse career starting in airline operations and sales, but eventually retired as an accountant. She holds a USCG Merchant Mariner OUPV and has completed her ASA 101/103/104.
They have learned to sail as a team and look forward to teaching others to do the same.
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ANDY DEEN
Captain Andy Deen is excited to introduce you to the world of sailing! As a former high school teacher, Andy paces lessons to match the goals and expectations of each student. His objective is to add as many tools to your toolbox to help you gain the confidence you need to skipper a yacht singlehanded or with crew. Captain Andy holds the USCG 25-Ton Master License with Auxiliary Sailing Endorsement and teaches ASA 101, 103, 104, 105, 106, 114 and 118. Andy lives with his wife Kathryn in Tampa, FL and is on the water most days of the year.
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JIM REED
Jim was born and raised in California. He learned to sail at the age of 10 on small lakes and harbors in California. Jim has sailed extensively in the Pacific Ocean, Caribbean Sea and Atlantic Ocean. He’s a retired firefighter who is now a professional sailor. Jim holds a USCG 50 ton Master Captain’s License with sailing and towing endorsements. Jim is American Sailing Association (ASA) instructor certified to teach course levels 101, 103, 104, 105, 114, and 118.
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STEFAN GASHUS
Captain Stefan moved to Florida in 2014 however his sailing career began in his youth in Halifax, Nova Scotia, racing sailing dinghies and keel boats until the North West Arm would freeze up. Later Stefan sailed out of the Sidney North Saanich Yacht Club in Victoria, British Columbia and participated in sailing races throughout the Pacific Northwest. Today Stefan offers charters out of St. Petersburg Florida to destinations in and around South Florida, the Bahamas and the Caribbean. In addition to holding a U.S. Coast Guard Master Captain’s License, Capt. Stefan teaches various sailing and power boating courses through approved American Sailing Association (ASA) and Recreational Power Boating Association (RPBA) schools.
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ALEX FAJARDO
For almost thirty years, Capt. Alex has been involved in teaching outdoor sports, from skydiving to kitesurfing. Fifteen years ago after his first week of sailing as a total novice, Capt. Alex knew he had to be a sailing teacher. Born in Barcelona, Spain, Capt. Alex first started sailing in England and Scotland, cold, wet and beautiful, where he gained his RYA Yacht Master Instructor Sail and his Power Boat Instructor qualifications. Since then, he’s been teaching students, from beginners to advance levels, in many places like Seattle, Bahamas, UK, Canary Islands, Gibraltar, Spain, Croatia and Greece. Capt. Alex is certified ASA to teach a wide range of courses from Basic Keelboat to Coastal Cruising, on monohulls and catamarans and holds a USCG Captain’s License.
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MICHAEL SHAWN
Capt. Michael has experience on a very wide variety of yachts. Over the course of 8 years, Capt. Michael has completed over 9,000 nautical miles of offshore deliveries across the US West Coast, Mexico, Canada, Bahamas, Caribbean, across the Atlantic, including the Mediterranean. Capt. Michael is looking to share his understand and experience in the World of Maritime.
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JON D. KINGSLEY, JR.
Capt. Jon has reached an age where ‘giving back’ to a lifestyle that provided him with such incredible adventure, memories and joy is part of Capt. Jon’s next chapter. He’s looking forward to sharing the skills and knowledge he’s acquired over the years. Capt. Jon can’t think of a better way to expose others, than to instruct. Hopefully, it ignites a similar passion in fellow adventurers.
Capt. Jon is a USCG 100T Master, ASA instructor, private pilot, advanced scuba diver (NAUI, SSI & PADI), entrepreneur and most importantly, when not in the air or at sea, a family man. From Jon: “Wherever you go, no matter what the weather, always bring your own sunshine!’
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RYAN FORSYTH
Captain Ryan is thrilled to be sharing the joy of sailing with you! He has been sailing almost literally since birth: he was out the water strapped into his car seat in the cockpit when he was just months old. He grew up in Annapolis, MD, sailing, racing, and teaching on everything from dinghies to 45ft race boats. He’s extensively sailed the Chesapeake Bay, East Coast (from Cape Cod to Norfolk and everywhere in between), the Puget Sound, and completed a few Bermuda trips. He’s a marine engineer by training, and enjoys running and backcountry skiing when not on the boat.