In December 1966 the Civil Aeronautics Board gave Caribair sweeping authority to extend its Foreign Air Mail Route 59 to serve all major Leeward and Windward Islands all the way south to Trinidad, thus bridging the entire Caribbean to the very doorstep of the South American continent. 

However, because of the difficulties Caribair encountered in securing approval from the various island governments along the route, service to only three islands – Martinique [Fort de France], St. Lucia [Castries] and Barbados [Bridgetown] – was inaugurated immediately. 

Because of the short notice of the plan to start these services, the Post Office Department authorized philatelic treatment but no cachet. 

This cover was one of only 21 pieces of mail carried on the inaugural March 2, 1967 Foreign Air Mail Route 59 flight from Charlotte Amalie, Virgin Islands to Fort de France, Martinique (where it was backstamped) and is listed in the Foreign Air Mail (FAM) Section of The American Air Mail Catalogue as F59-14a.

Eastern Air Lines absorbed Caribair through merger and took over the operations of FAM-59 on Jun 17, 1967.

Texas Air Corporation, parent corporation of Continental Airlines, New York Air and People Express, purchased Eastern Airlines. Eastern continued to operate as a separate airline. Operations were not integrated with any of the Texas Air owned companies.

As a result of labor disputes, Eastern filed for Chapter 11 bankruptcy protection and significantly cut back on its operation on March 9, 2989. After the initial reduction, Eastern slowly rebuilt its system with service to a few of the points previously served with a smaller number of flights. Eastern sold its lucrative “Shuttle” operation to Donald Trump and, in addition, sold off a large number of aircraft.

Eastern Air Lines ceased operations on January 18, 1991. This concluded the long history of an airline that could trace its roots back to May 1, 1928, with the first service of Pitcairn Aviation, Inc. In 1990, Eastern had sold its Central and South American routes to American Airlines and had been in receivership since declaring bankruptcy on March 9, 1989.