Captain Shawn Owen

Founder of Chronic Sailing | ASA Instructor | USCG Master Captain

Captain Shawn Owen is a lifelong sailor, licensed USCG Master Captain, and the founder of Chronic Sailing—a boutique charter and sailing instruction company based in Annapolis, MD.

With more than 30,000 nautical miles of offshore experience, including yacht deliveries throughout the Caribbean and extensive teaching across the Chesapeake Bay, Shawn is passionate about making sailing approachable, safe, and fun for everyone. He has taught hundreds of students—from solo sailors to families—how to confidently handle their boats in a wide variety of conditions.

Shawn’s training background includes ASA certifications, Boat U.S. Safe Boating instruction, and USCG OUPV & 100T Master License prep, making him one of the most well-rounded instructors on the Bay.

An accomplished musician as well, Shawn brings creativity, calm, and a laid-back vibe to every lesson or charter. Through Chronic Sailing, he delivers personalized sailing adventures and educational experiences designed to help clients build real skills—and unforgettable memories.

Michael G Hull                                                                                                           

This email address is being protected from spambots. You need JavaScript enabled to view it.

Mike began sailing as an adult, first on a Barnett 14 dinghy in 1993, owned a small swing keelboat, Tartan 33 (part owner), and since 2003 has owned and sailed a Sabre 34.  He took his first serious sailing course in the late 1990s, and has subsequently obtained numerous US Sailing and ASA certifications.  In Fall 2007 he joined the Command and Seamanship Training Squadron (CSTS) at USNA, and sailed as a CO or XO with Navy Sailing every summer through 2019. 

Mike was associated with J World Annapolis for 24 years, first as a student, and more recently as a big boat instructor from 2013-2024.  He joined Annapolis Sailing School as a captain in 2024.  He routinely teaches Basic Cruising, Bareboat Cruising, and Coastal Navigation, and has recently led several flotillas to the BVIs and the Abacos. Mike holds a USCG 50-ton Master’s License with a sailing endorsement.

Captain Boomies

Captain Boomies (aka Capt. Kate Hollingsworth) runs more than 100 different vessels a year as a delivery captain, boat instructor, and content creator. She earned her first sea miles as a young sailor on Long Island Sound, then worked her way up from deckhand to captain aboard private yachts worldwide. She enjoys the glamor of yachting but isn’t afraid to crawl into a bilge while cracking wise with the saltiest of sailors.

Holding a 200-ton USCG license, Boomies has raced across oceans, crewed for billionaires, and now creates fun, unfiltered videos about whatever floating thing she likes, while also helping marine businesses navigate social media marketing.

Based in her homeport of Baltimore, she specializes in new vessel deliveries, turning logistical headaches into seamless transitions. Her expertise ensures happy clients who keep coming back. (Fun fact: Dozens of Chesapeake Bay boaters have no idea their prized possession was first helmed by her.)

Follow her salty, silly, and occasionally educational adventures at captainboomies on your favorite platform.

Captain Hilary Howes Co-Ordinator

Hilary Howes International Broker, Delivery, Charter Captain, and Sailing Instructor

I’m a 25-ton Inland Master captain,  yacht broker, and ASA sailing instructor. I learned to sail in my native San Francisco Bay in the 70s, have raced and cruised in BVI, Bahamas and the east coast from the Chesapeake to Key West including the ICW. I’m an active member of the Annapolis sailing community, cruising on my Catalina 30 Laughing Spirit, and racing on friends’ boats. I’m a current member of the CAPCA Board of Directors, Herrington Harbour Sailing Association, and of the Chesapeake Catalina Yacht Club. My spiritual commitment to authenticity and service guides my work and in expanding the diversity of the sailing community.