Pan American Airways (1998-2004)

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In June 1998, the Pan Am brand was sold by a second incarnation of Pan Am to Guilford Transportation Industries, a railroad company headed by Tim Mellon of the Pittsburgh banking family. Guilford launched Pan American Airways with a fleet of seven Boeing 727s. The third incarnation resumed scheduled operations in October 1999 and flew to nine cities in New England, Florida, the Canadian Maritimes and Puerto Rico. The focus was on secondary airports such as Orlando Sanford International Airport instead of Orlando International Airport, and Pease International Airport and Worcester Regional Airport instead of the crowded Logan International Airport in the Boston area. Pan Am later had cooperative service arrangements with Boston-Maine Airways, a subsidiary incorporated by the airline in March 1999.

Guilford ceased operating Pan Am on November 1, 2004. Operations were transferred to Boston-Maine Airways, which resumed 727 service under the "Pan Am Clipper Connection" brand from February 17, 2005.