Day 1 - Old City Highlights: Jaffa Gate, Tower of David, Western Wall, Church of the Holy Sepulchre, and the Old City's Four Quarters on foot.
Day 2 - Ancient Jerusalem Underground: City of David, Hezekiah's Tunnel, Western Wall Tunnels, and the Davidson Center archaeological park.
Day 3 - Museums & Remembrance: Israel Museum in the morning, Yad Vashem in the afternoon, finishing at the Knesset if a tour slot is available.
Day 4 - Modern Jerusalem & Markets: Mahane Yehuda Market, Ben Yehuda Street, German Colony, and Mamilla Avenue, with an evening in the market's bars and restaurants.
Day 5 - Desert Day Trip: Sunrise at Masada followed by an afternoon floating in the Dead Sea, or alternatively a half-day in Bethlehem.