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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 Philadelphia, 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

Anna Quandt
Service Technician

Canvas Specialist

A career sailmaker, Amalia boasts over 25+ 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.  A native of El Salvador, Amalia now calls Annapolis home having lived here half her life.

Anna was born and raised in Annapolis with a Degree from Maryland Institute College of Art (MICA) in Baltimore. Her Art skills and creative abilities have transferred well to working as an apprentice sailmaker. In the six months she has been with the loft she has become proficient at all facets of hand work on sails and has developed her sewing skills for both Sail repair work and canvas projects. Anna can often be seen building our EZ Main stackpack style sail covers and working with Amalia on new sail construction. We have also put her Art skills to good use on several spinnaker graphics and stackpack graphics. Her attention to detail and cheerful personality has been a great addition to our loft. She is anxious to start sailing this spring.

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