TRAVEL is risk. No matter how close or convenient the destination, no matter how safe the conditions may be, or may be thought, travel unmoors the self from the familiar, the dependable; it causes one to see the comforts of home as things that can be left, and even lost. These effects might be slow to emerge or quick to vanish, but a person can be said never to have left home, indeed never to have lived, in whom that vulnerability doesn’t in some way make itself felt.
For William Whitehead the discomforts of travel in the 1820s were well enough known, and the risks of sea travel never far from thought. To Key West, where he would live for much of the next decade, shipwreck remained not just a clear and present danger but its life’s blood: as the uncharted reefs, treacherous currents, fickle winds and weather of the Florida Straits continued to jeopardize commerce, they also fed the wrecking economy of the Keys. It was from the wreck of his brother John’s own vessel in 1819 that Whitehead’s family could trace its initial acquaintance with Key West.1
When William and John boarded a schooner for Cuba in March 1829–William’s maiden voyage to the island–still greater terrors threatened. Pirates haunted the bays and cays of Cuba’s north coast ready, though less frequently than in the past, to wreak mayhem on the shipping of other lands. News of the massacre of an American captain and crew off Matanzas was still fresh when the Whiteheads set sail, making the prospect of violence at the hands of such marauders shockingly real.2
Even the approach to Havana did not put travelers instantly at ease. The entrance to its harbor, so narrow as to be nearly imperceptible, was bracketed by the ancient strongholds of La Punta and Morro Castle. Just inside glowered the Cabaña, a sprawling line of stone ramparts bristling with cannons (Whitehead counted more than 800) that commanded a view of every vessel in port.3
Cuba was and for the rest of the century would remain a possession of Spain. In the preceding twenty years, as most of her dominions were swept away by revolutions, Spain’s hold on Cuba, still its most valuable colony in the Americas, grew tighter. An atmosphere of surveillance and suspicion pervaded the island: “I was even warned,” Whitehead recalled, “not to indulge my harmless sketching propensities however trifling the object, or sound the notes of ‘Hail Columbia’ or ‘Yankee Doodle’ too loudly on my flute, or I might have a visit from the officials.”4 He would grapple, as did many of his countrymen, with the bureaucratic controls that applied to foreigners. Americans “accustomed to wander far and wide within our own extensive limits without ‘let or hindrance’” soon learned that this was not the land of freedom they had left.5
The capital retained a reputation for rampant lawlessness, but Whitehead was “soon agreeably disappointed in finding Havana during the day as orderly as any large city I had seen.” It was still advisable to keep to the more frequented areas at night. Robbers and murderers, if detected, were punished without mercy: among the first sights to greet the foreign visitor were the bodies of malefactors suspended from the gallows at La Punta “in full view from the harbor.”6
Yet here, in this metropolis of an autocratic régime where the threat of force was never far from view, lived the unmistakable charms of an Old World city on the very threshold of the New. At the sight of Havana–“the terrace roofs, the towers and steeples of the churches, the extensive fortifications”–Whitehead was transported. This city, its history reaching back 300 years when he first laid eyes on it, was like nothing he had known except in books: the journey suddenly brought to life those “descriptions and narrations which he had found it difficult to picture to his ‘mind’s eye.’” And after the brief sail from Key West, so dramatic a change seemed the work of “some little magic.”7 A decade later, as he concluded his sojourn in the tropics, Whitehead would combine the accumulated impressions and insights of several visits, publishing them in a Newark paper as fifteen “Letters from Havana.”
By the end of this first visit, Whitehead had no doubt seen more than he had words for. Probably among his sensations on the way out of Havana harbor was a growing unease. From Cuba he brought back the “varioloid,” a form of smallpox that would prostrate him for some days.8 But I suspect a slower, subtler disturbance may have been at work. The importation of Africans as slaves, illegal under U.S. law in 1808, declared tantamount to piracy and punishable by death since 1820, continued to flourish in Cuba. It did so with the complicity of American officials and the active participation of American merchants, who helped extend the trade illicitly to the United States. Together with the slave society that it sustained, this most insidious form of piracy, this most intractable of tyrannies would cast an ever darkening shadow over the life of William Whitehead and his homeland.
Copyright © 2018-2023 Gregory J. Guderian
 “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; pages 20-21 of the transcription contain the reference.
 For the 22 February 1829 attack on the brig Attentive, see Key West register, and commercial advertiser 5 March 1829 2:5-3:1, and a letter to the ship’s owner, dated 25 February 1829, in the Mauran Family Papers (MSS 560) at the Rhode Island Historical Society.
 “Letters from Havana I,” Newark Daily Advertiser 31 July 1838 2:1.
 “Letters from Havana I,” 2:2.
 “Many and deep are the anathemas which I have heard uttered by our countrymen in consequence of these restrictions.” “Letters from Havana II,” Newark Daily Advertiser 3 August 1838 2:1.
 “Letters from Havana VI,” Newark Daily Advertiser 17 August 1838 2:1.
 “Letters from Havana I,” 2:1
 “Childhood and youth,” 26.