Historical content courtesy of Jerry Wilkinson, Florida Keys historian

Up until the advent of the railroad, families usually lived on the ocean side as there was a better breeze, access to ocean transportation and fewer mosquitoes. In 1908, the first Islamorada post office was opened. The railroad depot was a full service depot complete with telegraph, railway express and waiting room.

The Islamorada Railway Station.


Engineering acquaintances of F.E.C. engineer William J. Krome began to build homes and the community of Islamorada was born. With time all of Upper Matecumbe became known as “Islamorada,” thought to be derived from the Spanish words for “island” and “home.”


By Jeane and Irving R. Eyster

Islamorada and More gives us accurate information on Islamorada and other parts of the Keys from the formation of the islands to recent events along with more than 100 photos.  This book is packed with information including the formation of the Keys, The Early Inhabitants, The Spanish Fleet, Early Florida, Pirates, Indian Key, The First Settlers, The Railway, Hurricanes, The Highway, Smuggling, Fishing, State Parks and much more. Authors Irving and Jeane Eyster have lived in the Florida Keys more than 60 years and as local historians have collected significant artifacts from all periods of Florida Keys history.  They have gathered information from the founding families who helped settle the Keys, and have lived much of this history. Islamorada and More is available at the Islamorada Chamber of Commerce, call Barbara Edgar at 305-393-0940 or email:


Excerpts from Islamorada and More:

Construction through the Upper Keys was quite rapid, as most of the water gaps were filled or crossed with short bridges. It took much longer to build the spans to the southwest, the Long Key, Seven-Mile and Bahia Honda bridges.

The railway had been completed to Islamorada … with a station, packing houses and railway sidings, allowing the shipping of limes, melons and pineapples. The train brought more people to the Keys: people traveled more. It was a short ride to either Key West or Miami from the Matecumbes.

The train brought more people to the Matecumbes (Lower and Upper) to fish and enjoy the tropical breeze and moonlit nights … The railway brought the tourists who needed places to stay and eat. Many cottages were built to accommodate them, with the restaurants following. Marinas were installed to oblige the boaters and fishermen. The Matecumbe Club was for the very wealthy visitors and had its own railway siding for their private cars.

In the early 1920s, the Keys were experiencing a boom.

One of the developers was George E. Merrick, son of a minister. Merrick developed the city of Coral Gables. His wife Eunice, granddaughter of Charles and Isabelle Peacock, pioneers of Coconut Grove, inherited her family’s property on the western end of Upper Matecumbe where they developed Caribee Colony (locally known as the “Colony”), a resort of more than 12 buildings.  Trains ran the South Seas Special to the resort, that left the F.E.C. Miami Royal Palm Park Station daily at 9 a.m. and returned at 7 p.m. The cars were put on a siding until time to return to Miami.

A Caribbean menu included a four-course dinner of steak or lobster with Key lime pie or coconut cake for $1.

Mr. and Mrs. J.W. Dumas ran the resort until 1935. They and the resort were both lost in the Labor Day hurricane.

Sign reads: "These wheels came from a miniature railroad located on the lower end of Long Key. The train was used to carry guests from the docks on the bayside through a small tunnel to the exclusive Long Key Fishing Camp on the oceanside."

Visitors to Islamorada can see this train caboose, located alongside US1.