Meet the Team: Greg Bailey

Tags: DiMillo's Freeport | DiMillo's Maryland | DiMillo's New York | DiMillo's on the Chesapeake | DiMillo's Yacht Sales | employee spotlight

One of the newest additions to the DiMillo’s family is Greg Bailey.  Greg joined the service team as a technician in 2023.  Greg’s interest in boats was kindled at age twelve when he began volunteering with his father and older brother aboard a tall ship in the Great Lakes. That early experience led to an almost twenty-year career in sail training ships that transported Greg all around the world. Much of that time was sailing as Captain, which allowed him to obtain a 1600 Ton Ocean Master license. During breaks in his time with traditionally rigged sailing vessels Greg signed aboard tugboats, tour boats, and a break-bulk freighter.


As is any professional sailor’s fantasy, Greg moved ashore. Once ashore, he worked at many different jobs, including line cook and middle school teacher but have finally found the right fit at DiMillo’s. Helping our customers solve boat related issues—after twenty years, Greg has discovered that all boats will have an issue sooner or later—so that they can enjoy the Maine coast and beyond gives him a profound feeling of a job well done.


Welcome to the team Greg!  Click here for more details about Greg and the Portland Team.

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