Concierge.com's insider take:
Although it's only about five miles from Jerusalem, a trip to Bethlehem (technically located in the West Bank) requires some strategic planning, as Israeli-registered guides, cars, and Israelis themselves are prohibited. Travelers should take a taxi from Jerusalem to the Beit Jala checkpoint on the Israel–West Bank border (the trip will take about 30 minutes and cost about $17). From there, transfer to a West Bank–based taxi for another 30-minute ride. Ideally, you should order one in advance: Dar Tesha taxi service employs reliable, English-speaking drivers (972-2-276-0302). You can make the trip in a day, but if you're staying the night, check into the Jacir Palace InterContinental Bethlehem. Its 250 rooms are spread between two modern towers constructed of off-white Jerusalem stone and a gracious palace wing that also contains the lobby, lounge, restaurants, and bars. Ask at the reception desk to arrange a city tour and driver (Hebron-Jerusalem Road; 970-2-276-6777; email@example.com). Visit Christian holy sites such as the Church of the Nativity on Manger Square, the Shepherds Field central market, and the winery of the Salesian Cremisan Monastery in the suburb of Beit Jala, about a ten-minute drive from the city center.