HOW was it that Christmas Day of 1829, just nine months after his departure from Havana for Key West and home, found William A. Whitehead back again, luxuriating in the pleasures of the Cuban countryside? Three of his published “Letters from Havana” are occupied with reminiscences of this return trip which, as he had “passed some time” the previous summer taking Spanish lessons,1 must have been in the works for some months. But we lack any clear statement of the motivation for an encore appearance.
His journey that autumn might well have been the last: his ship was nearly wrecked on the Bahama banks thirty or so miles from Cuban shores. Once safely arrived in the port of Havana, any hope of travel between the capital and outlying regions was attended with further aggravation: no such trips could be taken without first submitting an accurate, detailed itinerary to the authorities for their approval. That done, and once equipped with special passports bearing the Captain General’s “mark or flourish,” Whitehead and his older brother John set out in the waning hours of daylight on the 23rd of December.2
For the Whiteheads to attempt this journey without an entourage would have been difficult and even dangerous. Two nephews of their host in the countryside went ahead of them, riding abreast and armed with pistols and sabers. Next came a volante hitched to a horse and mule, with the calesero astride one of the beasts, as was customary. Another pair of riders followed the carriage, “a young gentleman of old Spain,” also armed, and William, on a stallion that seemed always on the verge of spiriting him away from the rest. (Whitehead forbears telling us whether he carried a weapon.) Two black servants brought up the rear; in charge of the trunks and other baggage, they were somehow perfectly capable of sleeping in their saddles as they rode.
The leaders kept their horses to a vigorous pace and, despite rutted roads sometimes thick with mud, the entire cavalcade managed to travel eighteen miles before dark. The party stayed the night at a wayside inn, where their sleeping quarters had to be shared with roosters and chickens, ensuring an obstreperous wake-up call early the next morning. There were other brief stops to rest the horses and to reinvigorate them with doses of aguardiente, applied to their hoofs, ears and nostrils.
The Whitehead convoy may have closely resembled other groups taking part in the usual Christmas exodus, when many of Havana’s well-to-do citizens decamped to the countryside, bringing with them all the “gayety [sic] and fashion of the metropolis.” Coffee and sugar estates in the hinterland were the favored destinations, their proprietors looking forward to several days of entertaining “city friends.”
To William’s eyes the terrain south of San Antonio de los Baños offered “an agreeable variety” of orderly plantations interspersed with uncleared thickets. Handsomely laid-out cafetales extended along the road on both sides, bordered with lime hedges. Crisscrossed by broad avenues dotted with fruit trees, their squares were filled with “coffee plants of the richest green, occasionally relieved by an early flower, giving them the aspect of delightful gardens.”
The goal of William and his brother, reached at midday on Christmas Eve, was a plantation belonging to a longtime acquaintance of the latter. Named La Calma, it boasted fruit trees of every description, and majestic royal palms lining the intersecting avenues, “forming colonnades which for symmetry and beauty could not be surpassed by the most superb works of art.”
In William Whitehead’s lavish descriptions the typical coffee estate seems a kind of earthly paradise for the planter: “the beauties of nature are around him, the air is salubrious, and all the comforts and conveniences of life are for the most part within his own control, for he produces upon his own premises almost every thing except clothing, that his family can require.” That such pleasures were the fruits of a slave system don’t seem to have detracted from these assurances of the “beauties and advantages” of life on the cafetal.
A fixture of the Christmas octave in the Cuban countryside were nightly public balls, made profitable by the gambling dens “located favorably in the immediate vicinity of the ball rooms.” A contemporary critic of Cuban society maintained that the Catholic feast days crowding the year contributed to a culture of idleness, which made Cubans of every social stratum susceptible to the “all-devouring cancer” of gambling.3
Whitehead watched in Artemisa, the town closest to La Calma, as monte players lost immense sums night after night to their banker hosts. With daylight came the illusory promise of making up the last evening’s losses with bets on cockfights for which, again, Cubans of all classes seemed to have a weakness.
The appeal of the balls for most “respectable” people, including Whitehead of course, was in the music and dancing. Some young ladies of noble lineage caught his eye, and he admired the Spanish country dances in which they took part for the variety and gracefulness of their steps. He visited also the hall reserved for the lower classes–“the hardy Monteros with their equally hardy daughters”–marveling at their mode of dancing and their music, emanating in part from what was presumably the Cuban güiro.4
Other than pure enjoyment, none of Whitehead’s known writings5 betrays any design to this holiday interlude, which lasted until January when he and his brother departed Cuba for Key West. It’s clear William availed himself of opportunities to study the landscape, economy and customs of the country, but edification seems to have taken a back seat to recreation. Any clue to more serious intentions must be sought in the few traces we have of his brother’s interests on the island.
John Whitehead could claim at least a decade of business experience in the Caribbean, which in 1829 he endeavored to parlay into an appointment as U.S. consul to Havana.6 Andrew Jackson’s administration dashed that hope, naming a seasoned diplomat to the position instead, but John was not discouraged from seeking other opportunities.
Ever since the U.S. took possession of the Floridas from Spain in 1821, it had fought a running battle with Spanish authorities for the return of archives relevant to their former domains. The most sought-after documents pertained to vast, valuable tracts in northern Florida whose ownership was fiercely contested. The government in Washington spent years trying to recover those papers, an effort actively opposed by private concerns in and out of Cuba, and with the connivance of Spanish officials.7
In February 1830, John Whitehead was named the clerk of a three-person commission set up to investigate the largest disputed land claim. The appointment necessitated a return to Havana, allowing him to maintain his ties there.8 One can only guess at what share in this work, if any, might have devolved to his younger brother, who marked his twentieth birthday in the same month and didn’t return north until April.9
Surely John’s original pretext for bringing William to the south–an “initiation under his instruction into mercantile life”10–continued to operate. But we ought not to exclude the possibility that Cuba in early 1830 planted the seed of an interest in foreign archives that was to be a preoccupation of William’s in later life. And the totality of his Christmastime experiences on Cuba can only have sharpened his skills, already well advanced, as an observer and chronicler of the world before him.
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, George A. Smathers Libraries, University of Florida; page 26 of the transcription contains the reference.
 Unless otherwise cited, quotations and other details in this article are taken from Whitehead’s “Letters from Havana X,” published in the Newark (N.J.) Daily Advertiser 3 September 1838 2:1-2; “Letters from Havana XI,” 6 September 1838 2:3-4; and “Letters from Havana XII,” 11 September 1838 2:1-2. Whitehead explained at some length the bureaucratic difficulties of traveling in “Letters from Havana II,” Newark (N.J.) Daily Advertiser 3 August 1838 2:1-2, writing that in the capital “you cannot obtain a general passport to go where you please, but every place must be particularly mentioned which you intend to visit, and the Captain General will grant you a passport accordingly; but if you are found wandering out of the expressed track, you are immediately stopped, and, very probably, confined until the matter can be referred to head quarters.”
 “No hay ciudad, pueblo, ni rincon de la isla de Cuba hasta donde no se haya difundido este cancer devorador. … Las casas de juego son la guarida de nuestros hombres ociosos, la escuela de corrupcion para la juventud, el sepulcro de la fortuna de las familias, y el origen funesto de la mayor parte de los delitos que infestan la sociedad en que vivimos.” José Antonio Saco, “Memoria sobre la vagancia en la isla de Cuba,” Revista bimestre cubana 2:6 (April 1832) 19-20.
 “Their music came from a curious instrument manufactured out of a gourd (played upon by scraping the surface), a sort of harp, and a violin.” “Letters from Havana XII” 2:2.
 Along with the “Letters from Havana” Whitehead left an account of his visit to La Calma in the first volume of the unpublished Memorandums of peregrinations by land & water (cf. “Childhood and youth” 26-27). Volume 2 of this memoir is held by the Key West Art and Historical Society, but the first has not been found.
 John Whitehead, Washington 25 May 1829, to President Andrew Jackson. ALS. Letters of application and recommendation during the Administration of Andrew Jackson, 1829-37. Record Group 59. National Archives and Records Administration. (National Archives film publication M639-26).
 A. J. Hanna, “Diplomatic missions of the United States to Cuba to secure the Spanish archives of Florida.” In: A. Curtis Wilgus, ed. Hispanic American essays. A memorial to James Alexander Robertson (Chapel Hill, N.C. 1942) 208-233, esp. 213-216.
 John Whitehead was appointed clerk of the commission on 15 February; see Record in the case of Colin Mitchell and others, versus the United States. Supreme Court of the United States. January term, 1831 (Washington 1831) 551-2; cf. 534. Presumably it was in that capacity that he appeared in Havana before U.S. consul William Shaler, whose job he had sought, to authenticate the handwriting of a witness. Deposition of John Whitehead, 6 March 1830, Correspondence of Richard Keith Call, Folder 5, Florida State Archives. This initiative overlapped with the Havana mission of future Florida governor Richard K. Call, who seems to allude to it in his report to Secretary of State Martin Van Buren. Richard K. Call to the Secretary of State, Tallahassee 28 March 1830, in Clarence Edwin Carter, ed. The territorial papers of the United States. Volume XXIV. The Territory of Florida 1828-1834 (Washington 1959) 384-388, esp. 387.
 “I again reached Amboy in April 1830….” “Childhood and youth” 27.
 Childhood and youth” 23.