Professional training and charter captains.

Swain Sailing has a staff of terrific instructors with years of teaching experience and in depth knowledge of our cruising grounds. We're confident that the quality of sailing education we provide is the best out there.

Evan Swain

Evan was raised in the BVI. He spent his formative years sailing, surfing and wind surfing - and wearing shoes as little as possible. He was on the tiller by age three and won his first dinghy regatta at age 10.  Evan relocated to Rhode Island to complete his high school years and attend college. After completing his Associates degree at High Point University, Evan decided to change tacks and pursue his passion for sailing and his gift for teaching.


Evan holds a degree in Marine Systems from the internationally recognized International Yacht Restoration School (IYRS) and is an ABYC certified marine technician.  He is ASA instructor certified through Catamaran Cruising and a US Sailing instructor. Evan runs the Jamestown, RI school in the summer and heads Swain’s BVI base in the winter months.


Burton Robson

As a resident of the British Virgin Islands, Burton has enjoyed thousands of nights in beautiful BVI anchorages and logged thousands of dives on the islands' outstanding reefs and wrecks. His qualifications and certifications include: ASA Sailing Instructor through Offshore Passage Making; PADI advanced dive instructor; a pilot and pilot trainer; marine mechanic; ABYC certified marine surveyor.

Burton voyaged thousands of miles as a singlehander, sailing from Toronto to South America while exploring anchorages and dive sites in over 35 Caribbean island nations. He's worked for BVI dive operators, charter companies and as a delivery skipper between Caribbean Islands. His work with the BVI Tourist Board included leading dives with journalists from International SCUBA magazines. Burton's passion for the BVI extends beyond the sailing and diving but also to the local people, history and culture.

His experience as a sailor and diver, intimate knowledge of BVI anchorages and dive sites, coupled with his love of instruction and progressive skill development, provide a unique opportunity to safely gain your sailing and diving certifications while chartering with Swain Sailing. Burton teaches in both Swain's BVI and Jamestown, Rhode Island locations.  


Meagan Woodman

Meagan was born and raised near Toronto, Canada. She started sailing at the age of ten on her family's Catalina 27, and quickly jumped into dinghies, earning full Sail Canada accreditation and advancing to the Race Team for her local Yacht Club. She spent three years racing Bytes and Laser Radials on the summer regatta circuit. Her keelboat racing in Ontario started on a C&C 29, where she was part of a successful crew, winning club races, regattas and distance races which led to her earning an award for Crew of the Year. A few years later, Meagan was crew on a J24 where she was part of the first ever all female crew on that race circuit.

Meagan spent five seasons as a Sailing Instructor, Race Coach and Head Instructor for youth sailing programs around Lake Ontario while completing her Bachelor's Degree in Medical Laboratory Sciences at the University of Ontario Institute of Technology.

Meagan moved to the Cayman Islands in 2018 where she spent 18 months as an Advanced Instructor for the Cayman Islands National Optimist Team, as well as running programs for adults and children. July 2019, Meagan joined Swain Sailing School's BVI branch as Program Director and Keelboat Instructor. 


Don Doggett

Don grew up sailing inland lakes in northern Wisconsin. Over 20 years ago, he purchased his first sailboat on Lake Michigan – which was a 22 foot Southcoast.  Since then he has owned and operated a variety of boat sizes and models. Don is an active and longtime member of Milwaukee Yacht Club and spends his time cruising the Great Lakes, racing regional sailboat regattas, and teaching adults how to sail.

Don is known for his dedication to teaching adult sailing and liveaboard cruising courses throughout Lake Michigan, Lake Superior, Southern Florida, and the Caribbean. Through years of teaching, Don has developed an acute understanding of why each student wants to learn how to sail and how to patiently work with students at their own pace.

He currently holds a USCG 100-ton Master Captains License and is authorized to teach USCG Merchant Mariner courses, including Operator of Uninspected Passenger Vessel (OUPV or 6-Pack) and Master Captains courses. He is trained as a first responder and maintains first aid and CPR certifications.


Scott Litster


Scott is an avid sailor who has a passion for teaching others how to sail with confidence. He creates a fun and relaxing on-board experience while keeping safety his first priority. Scott is an ASA certified instructor for Basic Keelboat through Advanced Cruising and Catamaran Cruising levels with 30 years of experience on the water inshore, near coastal and offshore with both monohulls and catamarans. He has also achieved his USCG Master Captains license with Sailing and Towing endorsements. From 2003 to 2013 Captain Scott owned and operated “Island Bound Adventures Sailing Academy” in Grapevine Texas where he earned many Outstanding Instructor awards and a few Outstanding School awards. His sailing includes local lakes, The Channel Islands, Eastern US, Tahiti, most of The Bahamas, Dominican Republic, Puerto Rico along with most islands between Puerto Rico and Grenada. His most rewarding sailing experience has been instructing collage students on a 35 day Sailing and Leadership program from St. Maarten to Grenada and back. For several years Scott lived and cruised on his 43’ Jeanneau “Believe in the Sea”.


In addition to Scott’s passion for sailing and training sailors, he is also an Aircraft Maintenance Technician and a licensed pilot. He has raced motorcycles off road, crewed for the worlds fastest piston engine/propeller driven aircraft, rebuilt a 1968 Beechcraft single engine airplane.

Michael Merritt

Mike is a career mariner with extensive sailing experience and over 30 years in the offshore industry. He’s worked in over 40 countries in all corners of the globe. Mike holds degrees from Massachusetts Maritime Academy and Cornell University with extensive training, managerial experience and certifications in all aspects of marine operations including navigation, offshore survival, radio operations, mooring analysis, anchor handling, stability and trim, bridge resource management, maritime security and QHSE (Quality, Health, Safety and Environment).

Mike is a USCG Master Mariner and an ASA Instructor through Offshore Passage Making.


Norman Martin

Norm is a lifelong sailor. When he was 10, his parents bought a cruising boat, sold the house and voyaged the US East Coast and Bahamas for two years. A few years later, his first job was as a sailing counselor on Cape Cod. Norm has been teaching sailing almost ever since. He has worked in NY, Annapolis, Boston, and all through the Caribbean as a cruising instructor. He understands living aboard. More importantly, he loves the work. Norm is very familiar with the US Atlantic Coast and Caribbean. In the early 1970s, Norm started crewing on the big yachts of the day. He was first mate on many New England and Caribbean passages qualifying him to skipper on ocean deliveries; and has served as delivery skipper on numerous North-South and return deliveries over the past decade.

Norm has worked for Swain since 2007.  He is an ASA instructor through Offshore Passage Making as well an ASA instructor evaluator. Norm is also a US Sailing certified Cruising Instructor and a NauticEd instructor/evaluator.  He holds a USCG OUPV license including authorization to teach OUPV courses.

Rob Swain

Rob has taught sailing in the BVI for over 25 years. He directed the Tortola branch of Offshore Sailing School for 8 years before starting Swain Sailing School, now in its 18th year training sailors in the BVI.

Rob holds a US Coast Guard Master One Hundred Ton license; US Sailing instructor certified through Passage Making; American Sailing Association instructor certified through Advanced Coastal Cruising and Catamaran Cruising. Rob has delivered up to 54' sailing yachts East Coast to BVI and BVI to St. Martin and Antigua. He has taught Coastal Passage Making from the BVI to St. Martin and St. Barths for 18 years. He has also lead our Passage Making/delivery course BVI- Bermuda- Newport in the Spring and Newport- Bermuda- BVI in the Fall for the past five years. Rob raced professionally 89-91.

Rob is a  recipient of the ASA Instructor of the Year award 2017.


Jimmy Slater

Jimmy is an ASA Instructor who started his teaching career in the Grenadines and is the recipient of the ASA Instructor of the Year award in both 2017 and 2018.

Jimmy was born in Guyana and started out working in the gold and diamond mining industry there. He migrated to St. Vincent and the Grenadines 20 years ago. He was able to sail those beautiful cruising grounds for quite some time living out his passion for sailing.


In 2008, he began working as a freelance skipper for several different charter companies doing weekly charters and deliveries along the windward, leeward island chain. Jimmy became an ASA instructor in 2014. Other than sailing and meeting people, Jimmy also enjoy listening to all types of music and art.

Alex Rocca


While Alex Rocca learned to sail in 1980 as a teenager, he also enjoyed a diverse career before dedicating his time to teaching sailing. Alex owned two pizzerias for over 25 years and also enjoyed a long career as a Real Estate executive for a railroad.


In his 20s, Alex also had a boxing career during which time he attempted to qualify for the 1988 Seoul Olympics. Over the past three decades he has also coached Men’s and Women’s Rugby teams and Referees.

Alex has sailed over 15,000 NM with destinations from Martha’s Vineyard to Bermuda, to the Bahamas and to the Virgin Islands. He has made long deliveries to and from the Virgin Islands. His love for the sailing and teaching is apparent to all his students. He currently holds ASA instructor certifications through Catamaran Cruising and a USCG OUPV Captains license. He lives aboard his own sailboat and make trips south in the winter and north in the summer.