Neighborhood: Upper East Side
Address: 830 5th Ave.
The Trump-Wollman Rink has been a Central Park staple for over 60 years. The surreal fact of an open-air skating pond inside the tranquility of the park, the cityscape looming around the edges, provides a classic holiday backdrop. Even the most jaded girlfriend will appreciate the gesture. And bonus: It's not nearly as crowded as Rockefeller Center's tourist-clogged rink.