WHEN DOING BUSINESS at Madeira, Christopher Columbus was some six hundred miles southwest of Lisbon, surrounded by an ocean thought to be scattered with more islands like it awaiting discovery and colonization. Even the known landfalls were far over the visible horizon. Santa María, the nearest of the Azores group, was more than five hundred miles northwest and eight hundred miles west of Lisbon. The Canary Islands were three hundred miles to the south of Madeira, off the West Africa coast, and the Cape Verdes were more than eight hundred miles farther southwest. The existence of these volcanic archipelagos had been promised by legend and hearsay and scholars of antiquity, and had yielded up to persistent daring and curiosity. Cartographers imagined many more of them, still farther west, and mariners had every reason to expect to find them, given past successes.

The Portuguese led the discovery (or rediscovery) of the Atlantic islands in the fifteenth century. The Madeiras were found and their settlement begun between 1419 and 1425; the first islands in the Azores archipelago were reached in 1427. The first Portuguese expedition to the Canaries, which had already been the subject of a French colonization effort, followed in 1440. Settlement of the Azores then began, and the Portuguese pressed southward along the West African coast, their vessels sighting the Cape Verde Islands sometime between 1456 and 1462.

More distant finds were promised. In 1448, a captain of one of Venice’s Flanders Galleys, Andrea Bianco, drew a world map while in London that demonstrated considerable knowledge of Portuguese discoveries, including several unlabeled islands that may have been an early recognition of the Cape Verde archipelago. Farther yet to the southwest, Bianco drew an enigmatic “authentic island” (Ixola Otinticha) that some would argue represented a secret Portuguese discovery of northeastern Brazil.

As the ocean yielded its final confirmable landfalls in that great triangle of trade and colonization—nearly one thousand miles west from Lisbon to the farthermost of the Azores, then fifteen hundred miles south to the Cape Verdes, and some eighteen hundred miles east-northeast, through the Canaries and the Madeiras along the West African coast back to Lisbon—the Portuguese combed through legend and anecdote, looking for some actionable evidence or encouragement. In 1452, Portugal’s Diogo de Teive sailed 150 leagues (about 450 miles) to the southwest from Fayal in the Azores and on his return completed the discovery of the Azorean archipelago by finding the westernmost islands, Flores and Corvo. It was also said that Teive then sailed on, far into the North Atlantic, beyond Ireland, and that he suspected land lay to the west when he turned back without sighting it, leaving some to later argue that he may have reached the Grand Banks.

Other Portuguese voyages, real and alleged, productive and otherwise, followed. Goncalo Fernandes de Tavira made a 1462 voyage to the northwest of Madeira on which he was said to have seen land, but there was nothing in that direction other than the known Azores, unless he had carried on all the way to northeastern North America. That same year, João Vogado went looking for two imaginary islands, Capraria and Lovo; he returned without any sightings. Although the Portuguese had not given up on finding the next volcanic peak in a trackless sea when Columbus arrived in Madeira, the profitable discoveries had diminished seriously, and the time had come to consolidate their holdings and defend their enormous maritime territory.

In September 1479, the Treaty of Alcáçovas with Spain granted Portugal the Azores, the Madeiras, the Cape Verdes, West Africa’s Guinea coast, “all other islands which shall be found or acquired by conquest [in the region] from the Canary Islands down toward Guinea,” and the fisheries of the adjacent waters. The Canaries, where a conquest of islands still held by the indigenous Guanches had begun in 1478, were Spain’s sole possession among the known Atlantic islands, and Spanish vessels could not sail south of them without Portugal’s permission. Portugal’s treaty rights were then encoded for all of Christianity in Aeterni Regis, a papal bull, or writ, of 1481.

The year of Alcáçovas was a busy one for Columbus. He returned to Genoa to testify in the suit over the sugar contract. He also married around this time Filipa Moniz Perestrello, the daughter of a Portuguese noble, Bartolomeu Perestrello, who had been dead for some twenty years but had been the first governor of the island of Porto Santos in the Madeiras. The governorship was hereditary, and when Columbus married Filipa, it was held by her brother, Bartolomeu the younger.

A Genoese wool worker of limited education in 1472 had rapidly transformed himself into an experienced seafarer, then a representative for sophisticated merchants and bankers, then a husband of a woman from a Portuguese family so noble that Filipa’s cousin Isabel secured the Castilian crown of Spain through the Treaty of Alcáçovas just as Columbus was marrying. In short order, he would be a promoter of a voyage scheme who was said by an ardent supporter to have mastered classical knowledge of geography and astronomy. The shape-shifting was breathtaking in its diversity of mobility: social, geographical, intellectual. John Cabot would provide a convergent example of how during the Renaissance someone from northern Italy could remake himself so ambitiously. Men were redefining themselves according to the opportunities they were creating.

Still, it was one thing to improve oneself through industry and ambition; it was another level of achievement altogether to make a dizzying ascent through the social strata by a spectacularly improbable marriage. If Columbus was a Madeiran factor of a merchant as prominent as Antonio Spinola, his status could have made him somewhat attractive as a spouse. But Filipa Moniz Perestrello’s family on both her mother’s (Moniz) and father’s (Perestrello) sides were of such nobility and courtly power that Columbus’s acceptance almost defied logic. The fact that Filipa’s father was of Genoese descent (or failing that, had been dead twenty years) might have allowed a low-born foreign commoner like Columbus to breach the family’s ranks.

But the main reason Columbus was accepted could well have been timelessly prosaic: The couple’s only child, Diego, apparently arrived in 1479, the same year the wedding is thought to have taken place. If Filipa was pregnant, legitimizing Diego would have required a marriage. On such a union of necessity the history of the world turned.

WHILE CHRISTOPHER COLUMBUS was making his way as a Genoese merchant’s representative in the Portuguese Atlantic realm, John Cabot was residing in one of Europe’s great cities of trade and culture. The republic that Venice ruled included the Italian cities of Padua and Verona, holdings on the Dalmatia coast and at Crete and Cyprus, and an Aegean portfolio that included the fortress town of Lepanto on the historically strategic strait of the same name. The diarist Marin Sanudo would boast in 1493 that his city “takes pride of place before all others, if I may say so, in prudence, fortitude, magnificence, benignity and clemency; everyone throughout the world testifies to this. To conclude, this city was built more by divine than human will.”

Cabot was probably born before 1450, which made him slightly older than Christopher Columbus, because on March 20, 1470, he was accepted into San Giovanni Evangelista, one of Venice’s four Scuole Grandi, or great religious confraternities. Founded in 1261, it was a prestigious lay group located in the sestier, or district, of San Palo on the island of Rialto, and would have had perhaps five to seven hundred members.

The scuole were charitable organizations that looked after their own members, many of whom were as poor as others were rich. They delighted in civic processions, particularly on Corpus Christi Day, when all the scuole, grand and minor, turned out to parade with candles and in costumed extravagance. The largest of them, the Scuole Grandi, were known—and criticized—for spending lavishly on their headquarters, and San Giovanni Evangelista featured art by Tinteretto and Carpaccio and housed a piece of the true cross acquired in 1361. During Cabot’s time in Venice, his scuola added an unusual outdoor atrium and gateway designed by Pietro Lombardo that was completed in 1485. But if Cabot was able to avert his attention from the conspicuous and indulgent splendor of the art, architecture, and processions, he would have found himself within a stone’s throw of considerable intellectual enrichment, even inspiration.

Near the adjoining church of San Giovanni Evangelista was a bell tower, where the hours were struck by two male figures bearing hammers controlled by a system of counterweights. At the foot of the remarkable tower, as Sanudo explained in 1493, “lectures are given in philosophy and theology, both in the mornings and afternoons, to whoever wants to go and listen; they are paid for from the funds of St. Mark’s.” If these lectures were being delivered during Cabot’s time in the Signoria, a free education would have been available to him rivaling that of the university in nearby Padua, which was also underwritten by the republic.

Cabot’s membership in a scuola as prestigious as San Giovanni Evangelista suggests he was well ensconced in Venetian society a half-dozen years before he secured citizenship. He had managed to join the confraternity when there was a waiting list for new members from established Venetian families. He must have had strong connections in order to enter its ranks since he was not a native-born citizen. That said, he was not wealthy; he made a donation on entry of four ducats while better-off entrants gave as many as ten. Surrounded by men of greater means and accomplishments, and living at the heart of a trading empire that held the European monopoly on the finest goods of the Orient through the Levant, Cabot can be forgiven for overreaching in whatever direction fate happened to turn him.

Cabot’s Venice was built on sea power. The republic defended fiercely its stranglehold on the supply of the East’s finest goods with a navy, built and equipped at the Arsenal, that had all but driven the rival Genoese out of the eastern Mediterranean and battled the Ottomans to maintain Venice’s domination of the European trade. All shipping out of Venice was controlled by the state, but with its merchant galleys, oversight was the most acute. These vessels held the Venetian monopoly on the transport of precious goods. Essentially anything expensive and unusual—Persian carpets, jewels, spices, rare books, elephant ivory—was consigned to their relative safety (and costly freight charges). Leased to merchants by public auction, the galleys serviced established trade routes in distinct flotillas. The flotilla known as the Flanders Galleys made an annual voyage north to Sluys in the Low Countries. England too had become an important destination for this northern flotilla. Southampton on the English Channel was first visited by the Flanders Galleys in 1319 and was chosen as the main English port for galley service following alarming riots against foreign merchants in London in the 1450s.

Venetian traders also sent out round ships, or carracks, that specialized in bulk commodities such as malmsey, the sweet white table wine sourced at Candia, Venice’s fortified station at Crete. But the galleys presented a particular spectacle of sails, oars, and pomp. The commander of a galley flotilla, the capitaneus, or captain, was a noble elected by the republic’s citizen assembly, the Great Council of nobles. The flotilla captain was served by what amounted to a seagoing court that included a priest, a notary, physicians, musicians, and personal servants. Constructed in the Arsenal, each vessel was manned by 170 oarsmen. Defense was provided by 30 bowmen (ballestraria), “impoverished gentlemen” or nobles, according to Sanudo, who were chosen by election. The crew, which numbered more than 200, included navigating officers, a purser and his assistant, a caulker, carpenters, a cook, and a cellarman. These ships were as resplendent in their accoutrements as the wares they conveyed, fitted out to serve as floating reception and banquet halls worthy of hosting monarchs and ambassadors. They were at once a form of commercial transport, trade fair, and diplomatic mission that was without equal in Renaissance Europe.

Venice was the perfect metropolis for an ambitious seafarer with new ideas of tapping the Orient’s riches to arise. Yet in searching for hard evidence of nautical savvy in Cabot’s formative years in Venice, one ends up finding for the most part a property developer. On September 27, 1482, he acquired for five hundred ducats a down-at-heels property, “certain houses of sergeants, partly habitable and partly ruined,” in the parish of San Giacomo dell’Orio in San Palo. The name of the parish—St. James of the Orient—makes no sense. Many explanations would revolve around a corruption of the proper name—one of them, de luprio, which means a dried swamp and would be appropriate to the particular terrain before it was developed, figures in the Cabot property records. But it is apt nevertheless that a man who would one day set out to prove a nonexistent westward route to Asia had owned real estate in a parish whose church was dedicated to a nonexistent saint of the Orient.

A month later, on October 30, Cabot made additional property plays in the town of Chioggia, about fifteen miles away in the southwestern corner of Venice’s laguna. He acquired two homes, one in the parish of San Nicolò dei Mendicoli, the other in San Nicolò de Chioggia, as well as “a stretch of meadow land and three salt works” within the town’s boundaries.

On January 13, 1484, Cabot pledged these Chioggia properties as security for the seventy-five-ducat dowry of his wife, Mattea. He was about to renovate and flip the San Giacomo dell’Orio property in Venice. In December that year, he sold the property, now featuring a “newly built house,” for sixteen hundred ducats, more than triple what he had paid for it about two years earlier.

The records for these real estate deals tell us he was the son of a merchant named Egidius (Giulio, Zilio), and had a brother, Piero, who had an interest in the San Giacomo dell’Orio property. We also hear about his Venetian wife, Mattea, and when Cabot sells the San Giacomo dell’Orio property on December 11, 1484, Cabot is identified as the “father of a family of sons.” At least two of his three sons thus were born by then, and were probably toddlers.

Property deals were but one part of Cabot’s entrepreneurial ventures. He was identified in a number of confraternity references as a pellizer, a trader in hides, which would have been mainly those of sheep and other domestic animals. But his dealings also could have extended to the furs that lined the somber Venetian cloaks and to wool, even English wool, as one 1482 record calls him more broadly a merchant, and the terms of his 1476 citizenship would have given him plenty of leeway in the sort of business he conducted. Venetian records also capture Cabot in October 1483 selling a female slave in the Venetian territory of Crete; he had purchased her somewhere in the sultanate of Egypt, which extended all the way to Lebanon and Syria. Slaves were common in Cabot’s Venice. They were found serving as household servants and gondoliers, and in the case of women, they inevitably bore children to owners.

Property developer, hide dealer, slave owner: Nowhere in surviving documents on Cabot’s life in Venice do we find professional mariner, let alone aspiring explorer. Even so, he could have been to sea regularly as a merchant, and there are indications that his life at home in Venice moved in the margins of seafaring. The purchasers of the renovated property he sold in San Giacomo dell’Orio in 1484 were the sons of Taddeo da Pozzo, who in turn witnessed the will of the wife of Alvise Ca’da Mosto (Alvise Cadamosto), a Venetian explorer and merchant still alive in Venice in 1488 who made voyages to West Africa under the Portuguese in 1455 and 1456 and may have been the first to sight the Cape Verdes. A number of sailors and artisans involved in ship construction joined the confraternity of San Giovanni Evangelista the same year as Cabot; the nobles of Cabot’s scuola included Polo Balbi, whose brother Benedetto was close to the ship patron and cartographer Cristoforo Soligo.

Yet living as he did in San Palo, in the commercial heart of a major maritime trading center, and with a membership in an organization as large and as distinguished as San Giovanni Evangelista, Cabot probably can be linked to almost anyone interesting. At the same time, he unquestionably lived in one of Europe’s most vibrant, prosperous, and knowledgeable centers of maritime commerce. Recalling his time in Venice as he waited to board a pilgrim galley so he could visit Jerusalem, our Spanish traveler Pero Tafur would write how “each day I went about seeing many remarkable and delightful things. Every hour there came news from all countries of the world, for the sea-borne traffic is very great, and ships are continually arriving from all parts, and if one desires to have news of any place it is only necessary to enquire of the ships.”

And Venice had been the home of Marco Polo, who remained the most celebrated traveler in Cabot’s time. His late thirteenth-century adventures in the Orient proliferated through manuscripts and found an even wider audience in the late fifteenth century through Gutenberg’s printing press. Polo’s story continued to be the main reference for Europe’s knowledge of Asia’s riches, rulers, and geography. More than a century after the Mogul khans had given way to the Ming dynasty, Europeans, Columbus included, continued to expect that an empire ruled by the Great Khan lay in easternmost Asia.

More recently, a Venetian noble and merchant, Nicolò de’ Conti, who died in 1469, had traveled extensively in the Middle East, India, and Southeast Asia. He had spent his youth in Damascus and learned Arabic, and sometime between the late 1420s and the early 1430s, he had made an extensive journey by land and sea along Muslim trade routes that included visits to India, Ceylon, Burma, Java, Sumatra, and Borneo. In 1439 in Florence, the secretary to Pope Eugene III, Giovanni Francesco Poggio Bracciolini, interviewed Conti and set down his experiences. The Latin manuscript remained unpublished until the seminal year 1492, when Poggio Bracciolini’s material was incorporated into the fourth book of Cristoforo da Bollate’s Varietate Fortunae (vicissitudes of fortune). Bollate gave the Conti material the title India Recognita (Indies rediscovered); the dedication was dated at Turin on February 15, 1492, less than five months before Columbus set out to discover the Indies himself with a westward sea route.

Although Poggio Bracciolini’s account of Conti’s adventures perpetuated the idea that the Great Khan still ruled Cathay, it contained a wealth of information on the Indies, their peoples, and their riches. Columbus may have been influenced by this work, if not before setting sail in August 1492 then at least by the time of his second voyage in 1493. Cabot could have had his own worldview informed by word of the experiences of this celebrated Venetian long before Bollate committed the Poggio Bracciolini manuscript to print in Florence. Nevertheless, the only eyewitness account of an effort by Cabot to propound on the established trade routes to the East, set down by the Milanese ambassador in London in 1497, would leave a striking impression of a man whose knowledge base scarcely matched that of the average merchant wandering the Rialto.

The slave purchase and sale tell us Cabot had traveled at least as far as the Levant, the Venetian gateway to the Orient’s riches. The Milanese ambassador’s report gives ample cause to believe that if Cabot ever dealt in precious goods, he had a very poor grasp of how they reached him. Cabot’s milieu nevertheless teemed with shipbuilders, chart makers, and merchants who traded as far away as England, and he could have ventured this far afield, as animal hides, not to mention wool, were a major export there, carried as haul-back items on the Flanders Galleys.

His trade as a pellizer linked him to a critical aspect of seafaring: cartography, the trade pursued by Christopher Columbus’s brother, Bartolomé. Mariners relied on the one-of-a-kind charts called portolans that were drawn and painted on vellum. Similar to parchment, which was prepared from lambskin, vellum generally used calfskin, and was more robust and thus better suited to the harsh marine environment. Cabot might have supplied raw calfskin or prepared vellum for cartographers, and conceivably could have drawn portolan charts as well, as his future would contain evidence of his engineering and drafting skills, including an eyewitness reference to him drawing and painting a harbor plan.

Cabot developed a diverse résumé in Venice and was far from finished in expanding the limits of his interests and ambitions. This was an age of audacious polymaths. Leonardo da Vinci, who was roughly the same age, was working for the dukes of Milan from 1482 to 1499, producing paintings, the clay model for a massive equestrian statue, military engineering innovations, and the dome of a cathedral. To encourage innovation, the Venetian senate had passed the world’s first known patent law, the Statute on Industrial Brevets, in 1474, which granted individuals a ten-year protection within the republic for any “new and ingenious contrivance.” More than one thousand petitions were received by the Venetian government by the end of the sixteenth century, for inventions ranging from windmills, to poisons, to lasagna and meat pies.

The quantifiable, the measurable, were being harnessed by the imagination. Principles of geometry and mathematics transferred readily across disciplines. Construction required architecture, engineering, and surveying; surveying was a close cousin of cartography, which along with navigation shared with surveying the methodologies and tools of observation. A man who could work out the height of a building or point of land by knowing its distance and angle of elevation was working in the same discipline as a mariner using a quadrant or an astrolabe to determine his latitude at sea.

Acquiring and developing properties in Venice and Chioggia would have required in Cabot an expertise in construction in a marine environment, which in turn invited a facility with drafting and engineering. Cabot’s coming civil engineering schemes would be far more crucial to his future as an explorer than his experience trading hides around the Mediterranean. Yet the skill Cabot demonstrated above all was hustle, a willingness to take considerable risks not so much with empty oceans as with what could prove to be empty promises. He was also a man not so much constantly on the move as on the run.

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