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.

The wharfs of Rocky Neck are home to an artists colony and a semiprofessional theater that produces the works-in-progress of playwright Israel Horovitz. Nearby is Beauport: The Sleeper-McCann House, the dreamy house of interior designer Henry Davis Sleeper, who infused the 40 rooms with the decorating and architectural styles of the 18th and 19th centuries. Much odder is Hammond Castle, which was built by eccentric inventor John Hays Hammond Jr. Its hodgepodge of Roman, medieval and Renaissance elements includes a drawbridge, Roman baths and a laboratory Hammond had built for his experiments.

The Cape Ann Historical Museum houses an impressive collection of the paintings and drawings of native son Fitz Hugh Lane, whose 19th-century seascapes hauntingly depict the clipper ships and schooners so prevalent then.

A little farther north on Cape Ann is Rockport, a once-rough seafaring town that's now an artists' hamlet. Don't expect to find any wine bars to go along with the galleries, though. Until recently (and except for a period in the 1930s), the town had been dry since 1856, when a mob of women armed with hatchets raided the town's saloons, smashing bottles, kegs and barrels. The cottage of rampage leader Hannah Jumper stands in the town's main square. In 2005, the town voted to allow restaurants and inns to apply for liquor licenses but there are still no bars or liquor stores. The shopping district Bearskin Neck is filled with galleries, boutiques, cafes and the like. An outdoor deck overlooking Perkins Cove is ideal for boiled lobster dinners. Beachgoers will appreciate the fact that Rockport's 4 mi/6 km of pristine public sands at Halibut Point State Park never seem to be overcrowded.

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