Empire State Building

Try imagining NYC’s skyline without the towering spire of the Empire State Building. Impossible, right? Taking a mere 11 months to construct, the 1,454-foot-tall emblem became the city’s highest building upon completion in 1931. During your visit, pay special attention to the lobby, restored in 2009 to its original Art Deco design. You can also impress your pals with these tidbits while queuing for the observation decks: In 1945, 14 tenants were killed when a plane crashed into the 79th floor during heavy fog; a terrace on the 103rd level was once intended for use as a docking station for airships; and the topper’s three tiers of lights can illuminate up to nine colors at a time.

Brooklyn Bridge

No mere river crossing, this span is an elegant reminder of New York’s history of architectural innovation. When it opened in 1883, the Brooklyn Bridge was a feat of engineering: It was the first structure to cross the East River and, at the time, the longest suspension bridge in the world. (It also made use of steel-wire cables, invented by the bridge’s original designer, John A. Roebling.) Now it attracts thousands of tourists and locals, who enjoy spectacular views of lower Manhattan and other city landmarks (such as the Statue of Liberty and Governors Island) as they stroll its more-than-mile-long expanse. Heads up, though: You may run into the occasional cyclist trying to navigate through the crowds on the pedestrian walkway.

Central Park

Gotham’s love affair with its most famous green space is well documented in song, literature and film, but there’s still plenty to adore about the country’s first landscaped public park. Urban visionaries Frederick Law Olmsted and Calvert Vaux sought a harmonious balance of scenic elements: pastoral (the open lawn of the Sheep Meadow), formal (the linear, tree-lined Mall) and picturesque (the densely wooded paths of the Ramble). Today, the 843-acre plot draws millions of visitors to its skyscraper-bordered vistas in all seasons: sunbathers and picnickers in summer, ice-skaters in winter, and bird-watchers in spring and fall. It’s also an idyllic venue for beloved cultural events like Shakespeare in the Park and the New York Philharmonic’s annual open-air performance.

Chrysler Building

We won’t argue if you want to call this glimmering pinnacle of Art Deco architecture NYC’s most eye-popping skyscraper. Triangle-shaped windows in its crown are lined with lights, creating a beautiful effect come nighttime. Oozing a moneyed sophistication oft identified with old New York, the structure pays homage to its namesake with giant eagles (replicas of ones added to Chrysler automobiles in the 1920s) in lieu of traditional gargoyles and a brickwork relief sculpture of racing cars, complete with chrome hubcaps. During the famed three-way race to construct Manhattan’s tallest building, the Chrysler added a needle-sharp stainless-steel spire to best 40 Wall Street—but was outdone shortly after its completion in 1930 by the Empire State Building.