After college, life at sea beckoned. Bolster spent years sailing and was licensed by the United States Coast Guard as Master of Motor, Steam & Sail vessels, 200 gross tons, all Oceans. Eventually he came ashore to a history faculty position at the University of New Hampshire.

Bolster is noted for writing Black Jacks: African American Seamen in the Age of Sail, a New York Times Book Review Notable Book of the Year, and he recently published The Mortal Sea: Fishing the Atlantic in the Age of Sail, which won numerous prizes. He also writes regularly for Points East: The Boating Magazine for Coastal New England.