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Assuming the reason for two days Yom Tov is because messengers could not reach those places in time to tell them the days of Rosh Chodesh, why is it that if someone visits Israel, but doesn't plan on staying there, they are required to keep two days Yom Tov? Following the logic above, once they are in the new location (e.g. Israel), they will surely know the correct dates for Yom Tov.

[my question also applies to the reverse case of someone from Israel visitng Chutz La'aretz]

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The truth is that while originally the practice was because of doubt about when Yom Tov would occur, that problem was solved when the calendar was fixed. Nevertheless the practice of two days of Yom Tov was retained as a custom.

In general an individual who travels to another local must retain their own customs while not publicly deviating from the local custom. As such an individual from chutz l'aretz who visits Eretz Yisrael is expected to retain their own custom against performing melachah, etc. on the "Second Day of Yom Tov" and pray the Yom Tov tefillos privately (M.B. 496:13). Conversely a "ben Eretz Yisrael visiting chutz l'Aretz must refrain from melachah on the second day of Yom Tov (Shulchan Aruch, Orach Chaim 496:3) even in private (M.B. 496:9).

There are a number of particulars in this so it is advisable, as always, to study and consult your Rav prior to acting.

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But while normally I understand that individuals keep their customs when they go to other places, in this case even their custom would "agree" that they don't need to keep two days. In other words, their custom says "In Chutz La'aretz you must keep two days," so when their in Israel, why should they have to keep it? –  yydl May 12 '10 at 15:00
    
Its not a halachic custom in the sense do what your fathers did when they visited Israel. Its do what your fathers did when they were not in Isreal. And also do this when you are in Isreal, even though they would not have. Dont forget your fathers would not keep 2 days if they live outside Isreal today, because they know when the month is. But that wont help them bec they dont live today. –  user1040 Nov 27 '11 at 13:19
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Just to add, the opinion of the Chacham Tzvi (167) and a number of other authorities is exactly this, that since the custom of the communities outside of Isreal to keep two days only applies outside of Isreal (for if the entire community would move to Israel they would only observe one day) so too a person who is visting Israel only observes one day. However, even according to this opinion, the reverse is not true, and a person from Israel visting a community outside of Israel is not required to observe the second day of yom tov (although practically he may not do melacha even privately so as not to deviate from the norm). The reason for this is that since observing the second day is based on the custom of the communities outside of Israel to perserve the earlier practice before there was a fixed calendar, he is not bound by this custom unless he decides to remain outside of Israel, thus joining the communities outside of Israel.

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