Did he bring along interpreters or any kind of language learning materials?
Luis de Torres was Columbus' translator on his first voyage. He had converted from Judaism to avoid the expulsion, and could speak Hebrew, Arabic, and Aramaic. Columbus' intent was to have de Torres make contact with traders from the Middle East once they reached Asia, and begin learning the local languages through them.
When Columbus left the Caribbean the first time, he abducted several Tainos to serve as proof of his successful voyage and as translators on future expeditions. Only one, christened Diego, returned with Columbus on his second voyage as the first Spanish-Taino interpreter. Meanwhile, Luis de Torres had remained behind as part of the force charged with establishing a fort. He is presumed to have been killed along with the rest of that expedition when the Taino rose up againt the Spanish.