As indicated on the letterhead, the Havana Special was a joint Pennsylvania/RF&P/Atlantic Coast Line/Florida East Coast train that went from New York to Key West, where it met a steamship that took a six-hour journey to Havana. The Labor Day Hurricane of 1935 wiped out Florida East Coast’s tracks to Key West, and the railroad did not rebuild them, so after that date the train terminated and met a steamship (and later a plane) in Miami. Despite the slightly truncated route, the train was even more popular in 1936 than 1935 and often ran with extra sections.
Click image to download a 213-KB PDF of this letterhead. Click here to download a 139-KB PDF of a matching envelope. Scans of this letterhead and envelope were contributed to Streamliner Memories by a reader.
Since Key West is mentioned on the above letterhead, it must be from 1935 or before. Below is an envelope from the collection of Florida International University with a picture of the train at dockside next to the steamship in Key West. The postmark dates this to 1933 and the penny stamps commemorate Chicago’s 1933 Century of Progress fair.
The connection to Havana stopped when Castro’s revolution led the United States to sever relations with that country in 1960. The name remained for a couple of years before being changed to East Coast Special in 1962, and then terminated a few months later due to Florida East Coast’s infamous strike. Below is an undated breakfast menu from the train. From the bathing suit styles on the front and the fonts inside, the menu was from the post-war period. The menu is from the Johnson & Wales collection, which says it has menus up through the 1940s, so the menu probably dates from about 1950 or shortly before.