Q: Did Elrond Ever Visit his Brother Elros in Numenor?
ANSWER: This is an interesting question. The answer is “no” but it may take some effort to convince everyone of that. All we know for sure is that after the Valar decided that enough Edain had reached the island of Númenor Cirdan sent no more mariners to Númenor. By the time Veantur reached Middle-earth in Second Age year 600 Elros had been dead for 158 years.
Because J.R.R. Tolkien never wrote about any reunion between Elrond and Elros, there is no reason to assume one happened. Hence, once Elros bade his brother farewell (presumably when he sailed away) they never saw each other again.
Nor could Elrond have communicated with his brother. The palantiri, gifts of the Eldar to the Faithful Númenoreans, would not be brought to Númenor or Middle-earth for thousands of years. Hence, Elros and Elrond had no direct way of sending messages to each other.
On the other hand, one could guess that Cirdan’s people occasionally sent ships to Aman early in the Second Age, even if they were only 1-way trips (although Tolkien never says return voyages were forbidden). Elrond could conceivably have sent a message to Tol Eressëa with a request that it be sent to Númenor. The Eldar of Tol Eressëa did befriend and tutor the Dúnedain in Númenor.
And so you could, by extrapolation, argue that maybe Elros could have sent a message back to Middle-earth via the Eldar of Tol Eressëa.
It is also possible that the Eldar of Middle-earth had some other less direct way of communicating with Aman.
But in the final analysis all we can say for sure is that Elros and Elrond would have been able to correspond with each other directly during the 50 or so years that Cirdan’s ships visited Númenor and then returned to Middle-earth. After that there is no evidence of any opportunity for them to have communicated with each other. At best Elros could have left behind a final message for his brother that Veantur could have conveyed to Middle-earth.
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Interesting I always wondered about why we don’t hear anything about ships of Lindon coming to Numenor (after the initial stage of tranportation of Edain and their goods of course), elven ships of Tol Eressea could go east to that island in the Second Age so why not Cirdan’s ships long after the colonization? Later it’s only numenorean ships (inlcuding Aldarion’s) visiting elves of Lindon, Cirdan and Gil-Galad, but not Cirdan and Gil-Galad’s elves going TO Numenor. Hmm theoretically there would not be any ban I think, and elves of Lindon would supposedly be able to explore the seas adn not only go ‘westwards’ to Undying Lands. There would be still many Teleri/Falathrim elves eager to brave the seas and explore islands, right? So maybe they could visit Numenor…but we simply are not given anything on that from Tolkien :).