Phone:  410.263.2380

After college (Marketing / Auburn Univ. 1989), I returned to my home town of Annapolis to take in one final summer of teaching sailing while I decided what to do for the rest of my life.  Things moved rapidly as by the fall of ’89 I was suddenly the marketing manager and default maintenance guy for Chesapeake Sailing School. Eventually, I ended up being a partner in ownership of the place.  Burnout quickly set in and by April of ’97, I left the place for greener pastures.  

Around 1995, I met a fellow named Mike Collins who lived at the marina where the sailing school was located and we schemed to form a yacht repair outfit that we could use in our spare time for extra cash.  Low and behold by 1997, we were going full time on this idea. Fiddlehead Boatworks, llc was officially in business on January 1, 1998. I made a valuable decision at this time to also subcontract for Watson Boatbuilding and cut my teeth manufacturing and repairing all variety of small craft under the tutelage of Craig Watson.   Now over 20 years later, Mike and I have dug ourselves into the rapidly shrinking club of yacht maintenance professionals located in the boating mecca of Annapolis.   

We are proud of our personal service to our owners.  In many respects our customers become almost family as we take care of their problems -( mostly boat related).  Some folks have brought 3 or 4 generations of boats to us for service. We pride ourselves on this fact.

Currently, we operate out of our shop at the Bacon Sails’ warehouse off of West St. in the Design District of Annapolis.  Bacons has been very instrumental in our growing customer base and we can be found there at all hours of the day and night fabricating and repairing components necessary for the active and safe operation of all manner of yachts.  Visit us there any time! We are also fully mobile and can come to your boat at a marina or a private dock. See you on the water!

Interested In Our Yacht Repair and Maintenance Services?

First step is to gather your ‘to-do’ and ‘wish’ lists, and call Winston at 410.263.2380.  He’ll help you schedule a site visit, and all flows from there. We provide free written estimates and contracts.

Locations We Serve:

Millersville, Severna Park, Arnold, Pasadena, Crownsville, Annapolis, Severn, Easton, St. Michaels, Kent Island, Baltimore, Columbia, Silver Spring, Rockville, Laurel, Bowie, Frederick

Counties We Serve:

Anne Arundel, Baltimore, Prince George’s, Howard, Montgomery, Frederick, Kent, Queen Anne’s, Talbot, Dorchester

Helpful Links:

Chesapeake Bay Yacht Racing Association –
Bacon Sails and Marine Supply – 
Chesapeake Outdoor Group –
US Sailing –