33 miles NE of Boston, 16 miles NE of Salem
The ocean has been Gloucester's lifeblood since long before the first European settlement in 1623. The French explorer Samuel de Champlain called the harbor "Le Beauport" when he came across it in 1606, some 600 years after the Vikings. The harbor's configuration and proximity to good fishing helped Gloucester earn the reputation it enjoys to this day. If you read or saw The Perfect Storm, you'll have a sense of what to expect here.
Gloucester (which rhymes with "roster") is a working city, not a cutesy tourist town. It's home to one of the last commercial fishing fleets in New England, an internationally celebrated artists' colony, a large Portuguese-American community, and just enough historic attractions. Allow at least half a day, perhaps combined with a visit to the tourist magnet of Rockport; a full day would be better, especially if you plan a cruise or whale watch.