Where: The top of the Empire State Building or the middle of Central Park are too predictable. Try something low-key and totally unexpected instead. Channel your inner Don Draper and ask a friendly barman at Grand Central's upscale, retro-chic cocktail lounge the Campbell Apartment to add a "Will you marry me?" message to a perfect Manhattan (just wrap it around the cocktail stirrer). Or take the subway to Brooklyn's DUMBO neighborhood, where you'll find the newly built Pier One at Brooklyn Bridge park—the stunning views of downtown Manhattan and the Brooklyn Bridge can't be beat.
Why: The history, architecture, and energy of this bustling metropolis sets the stage for a memorable moment.
Where to stay: Head to the hip Standard Hotel for a grown-up getaway in the hip Meatpacking District.