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This flag of Columbus appears in Crampton 1990 with a swallowtail. I've always had a doubt: is this a personal flag, one belonging to him (Colombus), or is it a position flag, the flag of the captain of the ships sailing to America (that is Colombus as a member of a hierarchy, not Columbus as a chap with a flag)?
Jorge Candeias, 15 October 1999
In the records written in his logbook, he says that October 12th, when they arrived at San Salvador (of course, he didn't know at the time where he was exactly), they landed in small boats from the 3 ships. Cristopher Columbus took from the Santa María the Royal Flag, and the captains of the Pinta and the Niña, a Captain's flag each. About this last flag, we know it was a capitana flag (a Spanish military term) for the expedition. It was used to distinguish the ships under the command of Cristopher Columbus (3 ships in this trip). It was not a personal/private flag belonging to him, but a sign of the fleet under his authority (each ship having a captain with this flag). It could have been swallowtailed, but only oral transmission remains of the flag. The symbols it contains (the "F" for King Fernando and the "Y" for Queen Isabel, crowned, and separated by a cross) are engraved at his burial mound in the Cathedral of Seville, but no flag shape is described.
This flag was given by the monarchs of Spain to distinguish the fleet under the command of Cristopher Columbus. That is, it was a flag to be hold by each Captain (one captain per ship) on Columbus' flotilla. I am no military expert, but I imagine it is something as if all the ships of the American 6th Fleet had a common flag to fly on each ship, and the fleet's commander-in-chief were Columbus.
José Carlos Alegría, 15 and 19 October 1999
Regarding the three ships of the Columbian expedition, the actual names of the ships were the Santa Maria, the Pinta and the Santa Clara. The Santa Clara was the smallest and therefore nicknamed the "the small one" or "Niña". This was also a reference to the Captain's last name and was therefore a play on words on two levels.
James J. Ferrigan, 19 October 1999