The Chesapeake Sailmakers Team

Chuck O'Malley
Founder and Loft Manager

Chuck is a lifelong cruiser and racer who was fortunate enough to turn his passion into a career. A former business major and CPA from LaSalle University in Phildelphia, Chuck started his sailmaking business in 2002, after working for a local sailmaker for a several years learning the trade.  He has 25 years of experience building and repairing sails, but his best skill is listening to clients needs and working with them to create solutions that make their sailing safer and more enjoyable.

Chuck has been on the water since the age of 4 and actively cruised and raced with his family growing up and continued a successful racing career with his wife and their crew on his boats over the years. Chuck along with his brother Bill designed and built their first 25 foot race boat and gained valuable experience in all aspects of rigging, fiberglass work, and boat equipment. His extensive background in boat repair, modification, deck layouts and yacht design provide him with insights that are uncommon in the industry. He has successfully collaborated with numerous racing teams and has guided countless numbers of extended cruisers on how to plan and prepare their sail inventories for offshore sailing. ​Chuck frequently offers seminars for yacht clubs and cruising groups and enjoys helping his clients enjoy their time on the water.

Amalia Regelado
Service Manager

Production Manager

Rob Kushner
Service Technician

Canvas Specialist

Amalia boasts over 20 years of experience with several large Sailmaking organizations working in all areas of new sail construction, sail repair and canvas work. She is very detail oriented and passionate about the quality of work leaving our shop. Amalia is charged with making sure all sails go through our 10 point check over process and  any work required gets detailed on work orders and communicated to clients.  

Rob grew up in the Annapolis area spending much of his youth sailing out of SSA. He has worked for Chesapeake Sailmakers for almost 4 years. Rob spends time working on sail repairs and installs but he has really carved out a niche as a canvas fabricator. Rob is responsible for all the design and fabrication of our EZ Main, stackpack style, sail covers. He has been instrumental in several design changes and has elevated our EZ Main product to a point that it is the highest quality and best functioning stackpack style cover on the market today. He is always busy building nearly 50 EZ Main covers a year. Rob is also an expert when it comes to canvas check over and repairs, whether its simple restitching or zipper replacement to replacing glass and new canvas fabrication.

Bill O'Malley

Special Projects

Jay Goldsberry

Front Office

Dealer Liason