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From Conquerors by Roger Crowley,

A second detachment of five ships under Estevao de Gama followed on April 1. The amplified expedition included a number of observers who would write eyewitness accounts. Some were anonymous; others identified themselves. They included a Portuguese clerk, Tome Lopes, and an Italian commercial agent, Matteo de Bergamo, both in Estevao's squadron, who recorded the progress of an expedition that...

Since information about the sea routes was crucial at the time and there was essentially a "covert commercial war between Venice and Portugal", why would the Portuguese have allowed an Italian on board?

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    Wasn't this a case of family connections? I don't have a source to hand.
    – MCW ♦
    Sep 23, 2021 at 9:37
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    If he doesn't have nautical knowledge, he wouldn't help much other navigators. The difficult part is how exactly to get there, a coarse map is not enough. But he would confirm the general picture of the Portuguese claims about where their products come from. And, given the small size of Portuguese population (~1M), they didn't have the luxury of going "Portuguese only". Many foreigners with some expertise were around (e.g. the artillery man Hans Staden). The Spanish could afford to be more restrictive.
    – Luiz
    Sep 23, 2021 at 13:21
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    Probably because the fleet was partially funded by Italian. Besides that, Italy was not a unified nation back then.
    – ThirstforKnowledge
    Sep 23, 2021 at 14:47
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    Where did the Italian commercial agent, Matteo de Bergamo, come from? Maybe his family came from Bergamo, a city which was ruled by the Venetian Republice from 1428 to 1797. But there is no proof that he worked for anyone in Venice and not for someone in Genoa, Venice's main rival, or for someone somewhere else in Italy, or maybe even worked for a Portuguese company.
    – MAGolding
    Sep 23, 2021 at 18:24

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This expedition was financed by the Affaitadi family (they were bankers), of which Matteo de Bergamo was a clerk. It is natural that the investors would ask the da Gama brothers to take one of their trusted clerks with them. However, after the expedition that took place in 1503, under the direction of Francisco de Almeida, King Manuel I forbade that Italian merchants would participate again in those expeditions.

My source is a PhD thesis (in Portuguese, pp. 233–234).

Here is a translation of the relevant passage:

The Affaitadi [family] kept its control over the commerce of sugar and molasses, even when, from the first decade of the XVIth century on, the offer of these goods (whose production originated from the Canary Islands) increased in Flanders. They funded the second expedition to India (1502–1503) by Vasco da Gama and his brother Estevão da Gama, in whose fleet they sent their clerk Matteo de Bergamo. The profits of this operation, in terms of the amount of money invested and the profit made, were estimated as being above 150%. The same procedure was used by them with the expedition by D. Francisco de Almeida (1503). When the Portuguese monarch forbade the Italian merchants from taking part directly in this business […] in 1504…

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