Bert Bossar
Bert Bossar
As an avid sailor and explorer, Bert thrives in helping others connect with the water. Both sellers and buyers enjoy not only his knowledge and expertise with boats, but also his personality and hands-on experience. Having lived and cruised the region for over a decade, Bert is very familiar with the Chesapeake Bay, where he skippers his J/42 Allegiant in mid-distance regattas. He also leads his crew in annual long-distance events such as the Annapolis to Bermuda, Annapolis to Newport, Newport to Bermuda and Marblehead to Halifax offshore races.
Bert is an active member of the Herrington Harbor Sailing Association and Eastport Yacht Club where he also chairs the 2026 Annapolis to Bermuda Ocean Race. He lives on the water in South Anne Arundel with his wife and their two stubborn Shepherds.
