Situated at the craggy tip of Cape Ann on a hazardous coast (hidden coves made it a favorite of rumrunners and smugglers), Gloucester, Massachusetts, was settled as a fishing colony in 1623. Located 40 mi/65 km northeast of Boston, activities in the area still center on the sea, and local maritime bravery inspired Sebastian Junger's The Perfect Storm
. Whale-watching boats leave from the town pier April-October. Do go, but remember that the whales aren't on a schedule, even if you are.
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