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The Dead Sea region is pleasant between October and April, but suffers from searing dry heat during the summer. Beginning the day with a tour of Masada can help beat the heat and the crowds. Ein Bokek, with its unique hotels and spas by the Dead Sea, attracts visitors even in broiling hot summer. Bethlehem is best early or late in the day if you want to avoid the crowds. Before you set out, check the hours for the Church of the Nativity. The area to the west of Jerusalem is agreeable any time of the year.
Some advanced planning pays off if you want to visit this region during a religious holiday, since transportation can be difficult during Jewish holidays like Yom Kippur and the Muslim observance of Ramadan. On Passover, Israelis tend to mob the Dead Sea. Similarly, Christmas is celebrated three times in Jerusalem and Bethlehem, according to the Western, Orthodox, and Armenian rites. Visit Manger Square on Christmas Eve for an unforgettable holiday, but book hotels far in advance.