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Gloucester, on Cape Ann, is a summer resort with a rocky coast and safe harbor. The town was settled in 1623 and has remained a fishing center. The harbor also bustles with traffic from sightseeing cruise ships and charter vessels. Charlie's Charters, 415 Main St., offers daily morning and afternoon fishing charters mid-May to mid-October; phone (978) 281-8992. Yankee Fleet Deep Sea Fishing, 121 E. Main St., offers all-day deep-sea fishing charters April through December and half-day fishing trips mid-June through September; phone (978) 283-0313. Other charter services are located along Essex Avenue. Learn More...