The first post office was established in February, 1829, and the first contract for mail service was awarded to owners of a small sailing vessel called the 'Post Boy' of about ten tons, which was to make monthly trips between Charleston and this city. Captain David Cole, with all the advantages of good seamanship, knowledge of coast, and superior education, was in command of this vessel, but for some very good reason, the monthly trips generally consumed nearer fifty days than thirty. Cape Canaveral was to be doubled in the route, and never did the mariner scan the clouds in the effort to double Cape Horn with more solicitude than did this worthy skipper to effect the same result at Cape Canaveral, but from different motives-the one being proverbial for its storms, and the other for its calms. Fretting did not bring the vessel any sooner than the winds and the current would permit. The mails were brought with regular irregularity. When they did arrive everybody knew it. He who was not certain that his expected letter would be prepaid by his correspondent put a 'quarter' (25 cents) in his pocket to satisfy old Uncle Sam for the cost of transportation (for that was the rate per letter at the time I speak of), and if perchance you subscribed to a newspaper, five cents more would put you all right with the postmaster, for this then enviable means of information that other Nations existed besides Key West." (Maloney).

This service proved so unsatisfactory that it was discontinued, and a route established between St. Marks and Key West. In August, 1832, a contract was awarded for the regular transportation of a mail between this place and Charleston, once a month. About 1835 Messrs. Lord and Stocker of Charleston obtained the contract for a semimonthly mail, and first class sailing vessels were put on the run.

About 1848 Messrs. Mordecai & Co., of Charleston, obtained the mail contract, and the Isabel, a remarkably fast and comfortable steamer of about eleven hundred tons, was put on between Charleston and Key West, which service continued until the commencement of the Civil War. The arrival of the Isabel in port was an important event. When she was sighted the fact was made known by the ringing of a bell on a tower at the agent's wharf. She frequently arrived at night and when that occurred nearly everybody sat up to await her arrival and hear from distant relatives and friends, from whom they had been cut off for two weeks. No family waited alone; those who did not have friends to eat midnight supper with them, went out to the homes of others, and the occasions were ones of jollification and social gathering. Happy, happy days, when all lived together in unity! When the Isabel neared the wharf the entire adult population would congregate there to get the first news of the outside world, and greet returning relatives and friends.

For some time prior to the Civil War occasional mails were brought to Key West from New Orleans and St. Marks, by a line of steamers owned in New York by Messrs. Morgan & Co. It was from such a modest beginning that the well known Morgan Line developed, which has since passed into the hands of the Southern Pacific Steamship Company, with the largest and fastest coastwise steamships in the United States. Shortly after the Civil War two fine, fast modern steamships - Cuba and liberty-were put on between Baltimore and Havana, touching at Key West both ways, until 1873, when the line was discontinued.

In 1873 Messrs. Mallory & Company inaugurated their service between New York, Key West and Galveston. They began with a few small steamers, which they replaced from time to time with larger ones, and they now have a fleet of twelve fast, commodious, finely equipped and admirably officered ships. In 1907 they established a line between New York and Mobile, touching at Key West both ways. Four, and frequently six, ships of this line touch at Key West weekly. The Mallory line is now part of that excellent transportation company, the Atlantic, Gulf & West Indies Steamship Lines. Under the management of Mr. H. H. Raymond, vice-president, the line has been brought to a high state of efficiency, and is the leading coastwise steamship organization operating in the Atlantic and gulf.

At the close of the Civil War the regular mail to Key West came via Cedar Keys, the terminus of the Florida, Atlantic & Gulf Central Railroad. For a number of years Miller & Henderson of Tampa, had the contract, and combined bringing the mails, with supplying this and the Havana market with beef cattle. If a drove of cattle was late in reaching Cedar Keys, or an obstreperous steer obstructed the lading, the mails were delayed from twelve to twenty-four hours.

Key West suffered from such irregular and imperfect service until in 1887, when Mr. Henry B. Plant, the pioneer developer of Florida, ran a line of steamers from Port Tampa to Key West and Havana. In the construction of the Mascotte and the Olivette he spared no expense, and the ship builders were instructed to turn out the very best steamships that could be built. After eighteen years constant service, the Olivette retains her supremacy as the fastest coastwise steamship in the United States, and she and the Mascotte can be depended upon, with the certainty of a railroad train, to make their runs within schedule time.

In 1895 Mr. Archer Harmon interested the people of Key West in a project to put a steamer on between Key West and Miami, the then southern terminus of the Florida East Coast Railway. He chartered the fast and commodious river steamer, Shelter Island, but before reaching Key West for her initial trip, she struck on shoals in Hawks Channel, and was a total loss. He next chartered the City of Richmond, a large side-wheel steamer, and changed her name to the City of Key West. She made a few trips under the original management, but the venture proving a failure financially, the stock in the company was taken over by Mr. Henry M. Flagler, who continued to operate the line between Key West and Miami until 1900, when the Peninsular and Occidental Steamship Company was organized, and the Mascotte, Olivette, Miami and City of Key West taken over by it. The principal stockholders in the company are Mr. Morton F. Plant and Mr. Henry M. Flagler. The Mascotte and the Olivette ply between Port Tampa, Key West and Havana, and make three round trips weekly, during the months of January, February and March, and two during the other months of the year.

In 1902 the City of Key West was sold, and the Shinnecock put on the run between Miami and Key West during the winter and the Miami the rest of the year. On the completion of the Florida East Coast Railway to Knights Key, in 1908, the line between Miami and Key West was discontinued, and the Montauk chartered for the run between Miami and Key West, during the winter season. The Miami plys between Miami and Nassau during three months in the winter, and in the summer takes the Knights Key-Key West run.

The Florida East Coast Railway will be completed to Key West January twenty-second, 1912, when mail service by water will be a thing of the past.

The first post-office -if a room where the few letters that were received in Key West at that time, could be called a "post-office" was in a building that stood on the corner of Caroline and Front streets, and occupied by the family of the postmaster. It was afterwards the home of Mr. Charles Tift, and subsequently occupied by Judge Angel de Lono. Its last tenants were the Misses Higgs, sisters of the Rev. Gilbert Higgs.

When Mr. Hicks was postmaster the office was on the northwest side of Front street, between Duval and Simonton, in the store of Hicks & Dusenbury. Later it was in one end of the stone warehouse on the Tift property on Front street, at the end of Fitzpatrick. When Mr. George Philips was postmaster it was in a room in the Russell House, on Duval street.

Under the administrations of Mr. Eldridge L. Ware, Mr. Joseph B. Browne, and part of that of Nelson F. English, it was in a small building on the southeast side of Front street, about a hundred feet from the corner of Duval. When this building was destroyed by fire in 1886, the post-office was moved to a small shed-like building on the southwest side of Whitehead street, on the government lot, at the corner of Whitehead and Caroline streets, formerly used as a storeroom by the lampist of the light-house service.

When Mr. Jefferson B. Browne was appointed postmaster in 1886, He erected on the corner of this lot a one-story building with a main office sixteen by thirty-five feet, and a smaller room sixteen feet square. He equipped it at his own expense with two hundred and fifty Yale & Towne lock boxes, the first that were ever used in Key West. This building was used as the post-office during Mr. Browne's term, and part of that of Mr. George Hudson, Mr. Browne's successor. In 1891 it was transferred to the new government building at the foot of Greene street.

-from "Key West: The Old and the New" by J. Browne. Published 1912.

"Key West: The Old and the New" by Jefferson B. Browne. Written in 1912, this is the most extensive historical text from that era. Fascinating...and not all pretty. You'll know more than most modern-day storytellers. Click on the titles below to read that chapter.
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