My youngest sister's birthday present was a trip to the Big Apple (how exciting!) complete with a train ride to the city, theater tickets, a Times Square hotel room, and a tour of Madame Tussauds.
While the intinerary was not nailed down to the minute, or even hour - my sister is much happier (translate: relaxed and comfortable) when she has a relative idea of the plan of action. Being that it was her first time to the city, I knew she'd most remember the iconic NYC elements: Times Square, the Empire State Building, Rockefeller Center, NBC... taxis, pizza, subway signs...
(The itinerary is based on simplicity, direction, and a underlying sense of... a plan of action.)