WILLIAM Whitehead considered few aspects of his first sea voyage worth transmitting to posterity. An unpublished memoir composed in later years but replete with details of his childhood and upbringing preserves scant information about this October 1828 journey. The vessel’s cabin was too crowded for its “three or four passengers”; the anonymous captain and crew of this nameless, “miserably-provided Brig” made Key West without serious incident; but nothing could arrest or temper the seasickness to which Whitehead early fell prey. The wretched provisions of the ship’s larder only seemed to aggravate it.1
His first impressions of the Florida Keys and of Key West, a place he would soon know inside and out, are likewise left to the imagination. We may conjure the dreary vessel rounding Key West’s southernmost point, where a 65-foot-tall lighthouse stood sentinel, then bearing north and nosing uneasily into port. The harbor approach would have disclosed a jumble of wharves, warehouses and skimpy frame buildings, some dating to a brief but turbulent period of military occupation. Commodore David Porter’s recently departed West Indies Squadron had effectively rid the Keys of the scourge of piracy, but Key West’s owners were still recovering from the Navy’s stranglehold on private development, and the growth of the island lagged behind its investors’ wishes.
Once on shore, when he ventured from the settled district Whitehead would have met a terrain thick with trees, shrubs and vines. Hardwoods, fragrant gums, wild fig, pigeon plum and mangrove trees flourished. Nowhere had he seen “a more pleasing variety of verdure.” Pleasing, but exceedingly difficult to control even in the streets of the town: new greenery would spring up “the moment the forest trees are cut away.”2
Almost more stubborn than the island’s luxuriant plant life was its persistent reputation as a breeding ground for disease and vice. Non-residents continually maligned the place for “the unhealthfulness of the climate and the character of its population,” charges that Whitehead would come to see and as a civic leader criticize as largely without foundation.3
As an eighteen-year-old newcomer, however, Whitehead could not help but be influenced by the opinions of two companions of his southbound passage: his older half-brother John, a proprietor and sometime magistrate on Key West who introduced him to the island and championed its commercial possibilities, and Stephen Russell Mallory, a youth close to William in age, raised in the Keys and now headed home from school in the North. Mallory’s parents, it turned out, were Key West pioneers: his late father Charles Mallory superintended some of the island’s earliest construction, while his mother Ellen Russell Mallory was held in high regard for her Irish humor, Catholic piety and ministrations to the island’s sick and dying. The widow Mallory now operated the town’s only “respectable” boarding house; William, once he became a public servant in his own right, would take meals under her roof.4
If the young Whitehead found Key West deficient in anything, it was the limited options for self-improvement. The usual pastimes of “billiards, bowling and card-playing” held no appeal for him. His new friend Stephen Mallory, despite the advantage of greater learning, now spent his leisure hours “in idleness” or on hunting and fishing expeditions. In time Whitehead would prevail: ever conscious of his own “deficiencies” he was to embark on “a course of solid reading,” and Mallory too would be swept up in this civilizing campaign. It would serve both men and the island well.5
Copyright © 2017 Gregory J. Guderian
 New York shipping lists show the brig Enterprise, captain Hitchcock, set to leave an East River wharf for Key West and Pensacola on 12 (originally 10) October 1828; this may have been Whitehead’s vessel. This Enterprise (not to be confused with a more famous brig of war of the same name, lost in 1823) continued to serve Key West into the 1830s. More details of Whitehead’s trip were likely contained in letters to family and friends in Perth Amboy, especially Catherine S. Brinley, “as she was made for many years the depository of every important circumstance affecting me.” This and other remarks about the voyage are from “Childhood and Youth of W. A. Whitehead 1810-1830.” A transcription of this memoir is held by the Florida History Department, Monroe County Public Library, Key West, Florida, and by the P. K. Yonge Library of Florida History, George A. Smathers Libraries, University of Florida; page 23 of the transcription contains the reference.
 William A. Whitehead, Notices of Key West for John Rodman Esq. St. Augustine, written December 1835, fol. 4v. Florida Miscellaneous Manuscripts Collection, P. K. Yonge Library of Florida History, Special Collections, George A. Smathers Libraries, University of Florida. The text was printed in Rember W. Patrick, ed. “William Adee Whitehead’s description of Key West,” Tequesta: The journal of the Historical Association of Southern Florida 1:12 (1952) (61-73) 66.
 Notices of Key West fol. 8v-9r; Patrick 70. A decade after Whitehead’s arrival such negative views remained: according to a letter of 1838, “The general opinion entertained of Key West is, that it is a sickly & very immoral place, the former abode of pirates & the present residence of wreckers, who are but little better.” Kenneth Scott, ‘The city of wreckers.’ Two Key West letters of 1838.” Florida historical quarterly 25:2 (October 1946) (191-201) 196.
 “Childhood and Youth” 30-32; see Rodman L. Underwood, Stephen Russell Mallory. A biography of the Confederate Navy Secretary and United States Senator (Jefferson, N.C., and London 2005) 10.
 Whitehead would claim credit for his friend’s devotion to learning at Key West, writing that “these literary pursuits of mine were not lost upon him.” Having assumed command of the Key West custom house in 1831, Whitehead named Mallory an inspector of customs the following year, “neither he nor I having the least idea to what prominence he would attain in consequence. … The appointment I gave him was his salvation.” Mallory became collector of customs in 1845 and was a U. S. Senator from 1851 until 1861, when he resigned from the Senate and accepted the position of Navy Secretary of the Confederacy. “Childhood and Youth” 30-32.