Boat Tours and Private Yacht Charters in Gloucester, Massachusetts. Experience the majestic beauty of historic Gloucester Harbor aboard the mighty Wejack, a classic fishing yacht beloved in Gloucester for its rich fishing history. Originally designed and built by master craftsmen for bluefin tuna fishing, the Wejack has sailed off the coast of Gloucester, America's oldest seaport and longest-operating fishing harbor. Aboard the Wejack, you can experience a genuine part of Gloucester's history. Sights include lighthouses, fishing boats, schooners, castles, grand mansions, beaches, and marine wildlife. Gloucester is part of Cape Ann on the North Shore of Massachusetts, just 25 miles north of Boston. Nearby towns include Rockport, Essex, and Manchester-by-the-Sea. Groups size up to 46 people. Full bar, catering, and sound system available. Tour Groups Welcome: (Bus parking available) Private Yacht Charters for corporate team building, weddings, group outings, fishing, and parties.